Synthesis, screening and docking of fused pyrano[3,2-d]pyrimidine derivatives as xanthine oxidase inhibitor

Article abstract of DOI:10.1016/j.ejmech.2017.03.002

In view of developing effective xanthine oxidase (XO) enzyme inhibitors, a series of 100 pyrano[3,2-d]pyrimidine derivatives was synthesized and evaluated for its in vitro XO enzyme inhibition. Structure activity relationship has also been established. Am

Full text of DOI:10.1016/j.ejmech.2017.03.002

Accepted Manuscript
Synthesis, screening and docking of fused pyrano[3,2-d]pyrimidine derivatives as
xanthine oxidase inhibitor
Manroopraj Kaur, Amandeep Kaur, Suhani Mankotia, Harbinder Singh, Arshdeep
Singh, Jatinder Vir Singh, Manish Kumar Gupta, Sahil Sharma, Kunal Nepali, Preet
Mohinder Singh Bedi
PII:
S0223-5234(17)30151-4
10.1016/j.ejmech.2017.03.002
EJMECH 9262
DOI:
Reference:
To appear in: European Journal of Medicinal Chemistry
Received Date: 5 June 2016
Revised Date: 23 January 2017
Accepted Date: 2 March 2017
Please cite this article as: M. Kaur, A. Kaur, S. Mankotia, H. Singh, A. Singh, J.V. Singh, M.K. Gupta,
S. Sharma, K. Nepali, P.M.S. Bedi, Synthesis, screening and docking of fused pyrano[3,2-d]pyrimidine
derivatives as xanthine oxidase inhibitor, European Journal of Medicinal Chemistry (2017), doi: 10.1016/
j.ejmech.2017.03.002.
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Synthesis, screening and docking oAf fuCseCd pEyPraTnoE[3,D2-dM]pyrAimNidUineSdCeriRvaItiPveTs as xanthine oxidase inhibitor
Manroopraj Kaura, Amandeep Kaura, Suhani Mankotiaa, Harbinder Singha, Arshdeep Singha, Jatinder Vir Singha,
Manish Kumar Guptab, Sahil Sharmaa,*, Kunal Nepalia,*, Preet Mohinder Singh Bedia,*
aDepartment of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar, Punjab, India
bLloyd Institute of Management and Technology, Greater Noida, UP, India

ACCEPTED MANUSCRIPT
Synthesis, screening and docking of fused pyrano[3,2-d]pyrimidine derivatives as xanthine
oxidase inhibitor
Manroopraj Kaura, Amandeep Kaura, Suhani Mankotiaa, Harbinder Singha, Arshdeep Singha,
Jatinder Vir Singha, Manish Kumar Guptab, Sahil Sharmaa,*, Kunal Nepalia,*, Preet Mohinder
Singh Bedia,*
aDepartment of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar, Punjab, India
bLloyd Institute of Management and Technology, Greater Noida, UP, India
Corresponding author: 1) Mr. Sahil Sharma
Department of Pharmaceutical Sciences,
Guru Nanak Dev University,
Amritsar, Punjab-143005, India
Phone: +918427007614
Email:ss.gq2009@gmail.com
2) Dr. Kunal Nepali
Department of Pharmaceutical Sciences,
Guru Nanak Dev University,
Amritsar, Punjab-143005, India
3) Dr. Preet Mohinder Singh Bedi
Department of Pharmaceutical Sciences,
Guru Nanak Dev University,
Amritsar, Punjab-143005, India

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1. Introduction
The key enzyme which plays a major role in the catalytic sequence of purine nucleotide
metabolism in humans and some uricotelic species is xanthine oxidase, a versatile
molybdoflavoprotein [1-2]. Xanthine oxidase catalyzed oxidative hydroxylation of hypoxanthine
and xanthine produces uric acid which leads to many diseases like gout and hyperuricemia [3].
Additionally, gout and hyperuricemia causes risk of chronic kidney diseases and cardiovascular
diseases [4]. Xanthine oxidase also generates superoxide anion and H2O2 which gets converted to
reactive hydroxyl radicals in the presence of chelated iron which further leads to pathological
conditions involving inflammation, metabolic disorders, cellular aging, reperfusion damage,
atherosclerosis, hypertension and carcinogenesis [5-6]. So it becomes necessary to selectively
inhibit xanthine oxidase which may result in the broad spectrum chemotherapy of gout, cancer,
inflammation and oxidative damage.
Xanthine oxidase inhibitors can be generally classified into purine and non-purine based on their
scaffolds mimicking the naturally occurring purines [7]. Some analogues based on purine like
allopurinol [8], 2-alkylhypoxanthines (hypoxanthine analogues) [9], pterin and 6-formylpterin
(pteridine analogues) [10], have been developed as potent xanthine oxidase inhibitors. Reports
suggest that purine based XO inhibitors interacts with activities of purine and pyrimidine
metabolizing enzymes like guanine deaminase, HGPRT (hypoxanthine–guanine phosphoribosyl
transferase), PNP (purine nucleoside phosphorylase), OPRT (orotate phosphor ribosyl
transferase) and OMPDC (orotidine-5-monophos-phate decarboxylase) which leads to Steven
Johnson syndrome and also causes worsening of renal function induced in some of the patients
[11]. Keeping in view these side effects, some non-purine based XO inhibitors like febuxostat,
flavonoids [12] and curcumin [13] derivatives, have been developed.
In view of developing effective non-purine based xanthine oxidase (XO) inhibitors, we have
designed N-acetylpyrazolines [2], β-acetamido compounds [14], azaflavones [15] and 4,6-
diaryl/heteroarylpyrimidin-2(1H)-ones [16]. Recently working on similar lines, our research
group synthesized and evaluated fused pyran derivatives viz naphthopyrans [17],
naphthoflavones [3], 2,4-diarylpyrano[3,2-c]chromen-5(4H)-ones [18], 4-aryl/heteroaryl-4H-
fused pyrans [19], benzochromone derivatives [20], (Fig. 1) for in vitro xanthine oxidase
inhibition in view of some of the potent non-purine xanthine oxidase inhibitors possessing

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benzopyran skeleton. The potent inhibitory potential of these analogues was attributed to the
interactions of pyran ring with the active site of enzyme as indicated by molecular modeling
studies.
In order to continue our research for non-purine based xanthine oxidase inhibitors and motivated
by the positive results of fused pyrans in inhibition of xanthine oxidase, the present study screens
a library of novel pyrano[3,2-d]pyrimidine derivatives for in vitro xanthine oxidase inhibition.
The inhibition type and the interaction of the most potent inhibitor with the amino acid residues
of the enzyme have also been figured out.
2. Results and discussion
2.1. Chemistry
Target pyrano[3,2-d]pyrimidines were synthesized via a sequence of reactions starting from
malononitrile, where it was treated with aryl/heteroaryl aldehyde and C-H activated acidic
compound in the presence of catalytic amounts of DMAP under microwave irradiation [19]. The
desired product 4H-Pyran derivative was thus formed. 4H-Pyran derivatives were then treated
with DMF-DMA (1 mmol) at room temperature to form respective imine intermediate which
was further refluxed with p-amino anisidine in glacial acetic acid to obtain the desired cyclized
product pyrano[3,2-d]pyrimidine (Scheme 1). In this synthetic protocol various substituted
anilines have been employed, although the reaction proceed only in the presence of anisidine
pertaining to its high nucleophillicity of nitrogen atom due to the electron donating effect of para
substituted methoxy group to the phenyl ring.
2.2. Bioassay
All the synthetics have been evaluated for in vitro xanthine oxidase inhibitory potential [21].
Apigenin and allopurinol were used as positive control. The IC50 values were calculated only for
those compounds having more than 60% inhibition at 100µM concentration as listed in Table 1.

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2.3. Structure activity relationship
Careful observation of Table 1 revealed that substitution of phenyl ring with electron donating
groups as Ring R remarkably enhances the xanthine oxidase inhibitory effect, whereas the
placement of phenyl ring with halo and nitro groups diminishes the effect. A positive effect was
observed with the increase in number of electron donating substituents on phenyl ring as Ring R,
whereas least potential was observed in the case of hetero aryl and naphthyl ring as Ring R. The
overall preference order of Ring R is as follows: phenyl with electron donating group > phenyl >
phenyl with halo and nitro groups > hetero aryl > naphthyl.
In the case of Ring X cyclohex-2-enone and 2H-chromen-2-one fused compounds showed
significant potential as xanthine oxidase inhibitor. The preference order of Ring X is as follows:
cyclohex-2-enone > 2H-chromen-2-one > 5-methyl-1H-pyrazole > naphthyl.
Compound 9d was found to be the most potent compound among all the synthesized pyrano[3,2-
d]pyrimidines with IC50 value of 7 µM.
2.4. Enzyme kinetics
Compound 9d was further investigated for the type of inhibition and enzyme kinetic study was
carried out [22]. The Lineweaver-Burk plot (Fig. 2) revealed that the compound 9d was a mixed-
type XO inhibitor. The pattern of graph shows that it is a form of mixed inhibition scenario. The
Km, Vmax and slope are all affected by the inhibitor. The inhibitor has increased the Km and slope
(Km/Vmax) while decreasing the Vmax. Moreover carefully observing the Figure 2 it was found
that intersecting lines on the graph converge to the left of the y-axis and above the x-axis which
indicates that the value of α (a constant that defines the degree to which inhibitor binding affects
the affinity of the enzyme for substrate) is greater than 1. This confirms that the inhibitor
preferentially binds to the free enzyme and not to the enzyme substrate complex.
2.5. Molecular properties
We also calculated the compliance of compounds to the Lipinski’s rule of five [23]. The three
most potent compounds (4d, 8d and 9d) were selected for the calculation of molecular
properties. These compounds are completely consistent with Lipinski’s rule (Table 2).

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2.6. Docking study
A docking study was also performed to investigate the recognition pattern between xanthine
oxidase and most potent XO inhibitor 9d, (Fig. 3). The 9d was docked into the salicylic acid
binding site of XO using Gold software. The 9d fits well in the XO binding cavity and stabilized
by electrostatic and hydrophobic interactions. The binding site residues and overall binding
mode of 9d was found to be is similar to those observed with fabuxostat [24] and salicylic acid
[25] (Fig. 3). The binding conformation of salicylic acid in the X-ray structure of XO revealed
that salicylic acid is sandwiched between Phe914 and Phe1009. Here, salicylic acid is involved
in “face-to-face” and “face-to-edge” pai-pai stacking interactions with Phe914 and Phe1009
respectively. In the docking conformation of 9d, the orientation of ring D was found similar to
the salicylic acid (Fig. 3b). The major interactions of 9d with XO include arene-arene
interactions with Phe914 and Phe1009 and H-bond interactions interaction with Asn768. The
aromatic ring D of 9d is positioned in a cavity formed by hydrophobic residues Leu873, Phe914,
Phe1009 and Val1011, Leu1014 and more precisely found sandwiched between Phe914 and
Phe1009 (Fig. 3b). Here, it is involved in “face-to-face” and “face-to-edge” pai-pai stacking
interactions with Phe914 and Phe1009, respectively (d = 4.473Å and 3.402Å; Fig. 3a). This
arrangement of energetically favourable arene/arene interactions [25] is also observed in the co-
crystal structure of XO with salicylate [26] and fabuxostat [24]. This play an important role in
stabilizing the binding positions of aromatic substrates and represent one of the key features of
substrate recognition by XO. The side chain amino group of Asn768 (H-bond donor) has shown
two H-bond interactions with the hydroxy-oxygen and methoxy-oxygen (H-bond acceptor) of
aromatic ring E (d= 1.936Å and 2.229Å, respectively). The aliphatic rings A and B gets oriented
near hydrophobic residues Leu648 and Phe649 and suggested to be involved in van der Waals
interactions. Further, the ring D gets oriented towards the molybdenum ion moiety at a distance
of 4.864 Å (Fig. 3b). The study suggests that 9d may block the activity of the XO sufficiently
enough to prevent the substrate from binding to the active site.
3. Conclusion
In conclusion, a library of 100 pyrano[3,2-d]pyrimidines was successfully synthesized and
1
characterized by using H NMR, 13C NMR and MASS. All the synthesized compounds were
tested for their in vitro xanthine oxidase inhibitory activity. Compound 9d was found to be most
potentenzyme inhibitor among the series with IC50 value of 7 µM. Enzyme kinetic study

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confirmed that the inhibitor 9d preferentially binds to the free enzyme and not to the enzyme
substrate complex (mixed type inhibition). Molecular properties calculation of the most potent
compounds (4d, 8d and 9d) proved their drug likingness as these compounds showed no
violation to the Lipinski’s rule of five. Docking study suggested that the compound 9d may
block the activity of xanthine oxidase sufficiently enough to prevent the substrate from binding
to the active site.
4. Experimental section
4.1. Materials and measurements
The reagents were purchased from Sigma Aldrich, Loba and CDH, India and used without
further purification. All yields refer to isolated products after purification. Products were
characterized by comparison with authentic samples and by spectroscopic data (1H and 13C
1
NMR). H NMR and 13C NMR Spectra were recorded on Avance III HD 500 MHz Bruker
Biospin Nuclear Magnetic Resonance Spectrometer. The spectra were measured in CDCl3
1
relative to TMS (0.00 ppm). In H NMR chemical shifts were reported in δ values using
tetramethylsilane as internal standard with number of protons, multiplicities (s-singlet, d-doublet,
t-triplet, q-quartet, m-multiplet, dd-double doublet) and coupling constants (J) in Hz (Hertz) in
the solvent indicated. HRMS was recorded on micrOTOF-QII Bruker Daltonik LC–MS/MS
High Resolution Mass Spectrometer. Melting points were determined in open capillaries and
were uncorrected.
4.2. Procedure for the synthesis of 4H-Pyrans [19]
A mixture of aryl/heteroaryl aldehyde (1 mmol), malononitrile (1 mmol), C-H activated acidic
compound (1 mmol) and catalytic amounts of DMAP (5 mol %) was exposed to microwave
radiation in a microwave reactor operating at 150ºC with the maximum microwave power of 400
W. After the completion of reaction (evident by TLC), reaction mixture was poured on crushed
ice and kept aside for some time. Then it was filtered and dried to obtain the desired product, that
is, 4H-Pyran derivative.
* C-H activated acidic compound in case of (e) was generated in situ from the reaction of
hydrazine hydrate and ethyl acetoacetate.

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4.3. Synthesis of pyrano[3,2-d]pyrimidines
4H-Pyran derivative (1 mmol) was further treated with DMF-DMA (1 mmol) at room
temperature to form DMF-DMA condensed product (imine intermediate). After the completion
of reaction (evident by TLC), this imine intermediate was refluxed with p-amino anisidine (I
mmol) in glacial acetic acid. After the completion of reaction (evident by TLC), reaction mixture
was poured on crushed ice and kept aside for some time. Then it was filtered and dried to obtain
the desired cyclized product, that is, pyrano[3,2-d]pyrimidine derivative.
1
13
The structures of all the synthesized compounds were elucidated by H NMR and C NMR.
Obtained spectral data was in accordance with assumed structures. The characterization data for
the synthesized new compounds is given below:
4.3.1.
(E)-N,N-dimethyl-N’-[3-cyano-4-(2-methoxyphenyl)-4H-benzo[h]chromen-2-
yl]formamidine (imine intermediate)
1
Greenish brown solid; Yield: 80%, mp: 160-167ºC. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.43 (1H, s), 8.18 (1H, d, J = 10Hz), 7.78 (1H, d, J = 10 Hz), 7.95-7.98 (1H, m), 7.49-7.52 (1H,
m), 7.47 (1H, d, J = 10 Hz), 7.16-7.21 (2H, m), 7.11 (1H, d, J = 10 Hz), 6.92 (1H, d, J =10 Hz),
13
6.85-6.88 (1H, m), 5.55 (1H, s), 3.90 (3H, s), 3.22 (3H, s), 3.18 (3H, s). C NMR (CDCl3, 125
MHz, δ, TMS = 0): 160.33, 156.64, 153.33, 144.07, 133.25, 133.07, 129.97, 128.25, 127.76,
126.38, 123.25, 126.13, 123.95, 123.75, 121.11, 120.68, 120.36, 118.02, 111.15, 74.14, 55.80,
41.06, 35.90, 34.85.
4.3.2. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-phenyl-6-oxo-7,10-dioxa]anthracene (1a)
1
Yellowish brown solid; Yield: 82%, mp: 172-178ºC. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.69 (1H, s), 8.34 (1H, s), 8.06 (1H, d, J =10 Hz), 7.73 (1H, m), 7.52-7.53 (3H, m), 7.46 (1H, d,
J = 10 Hz), 7.40 (2H, d, J = 10 Hz), 7.28-7.31 (2H, m), 7.22 (1H, d, J = 10 Hz), 6.88 (2H, d, J =
13
10 Hz), 5.65 (1H, s), 3.76 (3H, s). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 165.81, 165.02,
164.28, 161.41, 161.05, 159.76, 157.34, 146.85, 136.89, 133.56, 132.48, 129.14, 118.70, 118.54,
110.75, 103.29, 84.20, 83.94, 83.68, 60.25, 54.10, 53.78, 38.20. MS: m/z: 450 (M + H)+.

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4.3.3.
1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(4-methoxyphenyl)-6-oxo-7,10-dioxa]
anthracene (2a)
1
Yellowish brown solid; Yield: 84%, mp: 163-167ºC. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.33 (1H, s), 7.48 (2H, d, J = 7.7 Hz), 7.15 (1H, m), 7.06 (2H, m), 6.95 (2H, d, J = 7.4 Hz), 6.65
(2H, d, J = 7.1 Hz), 6.55 (2H, d, J = 6.9 Hz), 6.32 (2H, d, J = 6.7 Hz), 4.74 (1H, s), 3.77 (3H, s),
3.76 (3H, s). 13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 174.43, 168.24, 162.02, 157.74, 150.72,
150.20, 145.81, 135.43, 130.15, 128.44, 127.42, 126.85, 125.50, 121.54, 117.50, 117.32, 115.11,
114.28, 112.24, 97.90, 55.94, 33.20. MS: m/z: 480 (M + H)+.
4.3.4.
1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(2-methoxyphenyl)-6-oxo-7,10-dioxa]
anthracene (3a)
1
Yellowish brown solid; Yield: 81%, mp: 167-170ºC. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.37 (1H, s), 8.15 (1H, d, J = 7.8 Hz), 7.84 (1H, s), 7.59 (1H, d, J = 7.2 Hz), 7.32-7.49 (7H, m),
6.86-7.21 (3H, m), 5.52 (1H, s), 4.09 (3H, s), 3.71 (3H, s). 13C NMR (CDCl3, 125 MHz, δ, TMS
= 0): 174.40, 168.14, 162.02, 158.74, 150.72, 150.21, 145.80, 135.44, 130.11, 128.42, 126.86,
125.50, 121.55, 121.01, 117.34, 115.12, 114.24, 112.20, 97.94, 56.22, 55.94, 35.34. MS: m/z:
480 (M + H)+.
4.3.5.
1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(3,4-dimethoxyphenyl)-6-oxo-7,10-dioxa]
anthracene (4a)
1
Greenish brown; Yield 67 %, mp: 160-161°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0): 8.31
(1H, s), 7.99-8.01 (1H, m), 7.49 (1H, s), 7.27-7.30 (2H, m), 7.20-7.22 (1H, m), 7.12-7.15 (2H,
m), 7.07 (1H, s), 6.99-7.00 (1H, m), 6.88-6.90 (1H, m), 6.70-6.76 (3H, m), 5.09 (1H, s), 3.65-
3.74 (8H, m). 13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 156.12, 156.01, 155.05, 152.26,
151.92, 149.86, 147.80, 144.49, 128.09, 127.83, 126.21, 119.79, 109.25, 108.93, 107.31, 106.66,
100.45, 92.95, 51.26, 51.08, 50.65. MS: m/z: 510 (M + H)+.
4.3.6. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(3,4,5-trimethoxyphenyl)-6-oxo-7,10-dioxa]
anthracene (5a)
1
Brownish green solid; Yield: 86%, mp: 160-164ºC. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.33 (1H, s), 7.46 (2H, d, J = 8.5 Hz), 7.17 (1H, m), 7.09 (2H, m), 6.57 (2H, d, J = 8.5 Hz), 6.36

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(2H, d, J = 7.7 Hz), 6.02 (2H, s), 4.77 (1H, s), 3.75 (3H, s), 3.73 (3H, s), 3.72 (3H, s), 3.70 (3H,
13
s). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 174.46, 168.12, 162.02, 150.75, 150.26, 145.83,
136.24, 135.48, 129.44, 128.40, 126.86, 125.52, 121.59, 117.54, 117.32, 115.14, 112.25, 106.47,
97.92, 56.59, 56.20, 55.97, 39.84. MS: m/z: 540 (M + H)+.
4.3.7.
1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(4-hydroxyphenyl)-6-oxo-7,10-dioxa]
anthracene (6a)
Reddish green solid; Yield: 83%, mp: 162-165ºC. 1H NMR (CDCl3,500 MHz, δ, TMS = 0): 8.34
(1H, s), 7.45 (2H, d, J = 7.8 Hz), 7.12 (1H, m), 7.03 (2H, m), 6.89 (2H, d, J = 7.6 Hz), 6.61 (2H,
d, J = 7.3 Hz), 6.55 (2H, d, J = 7.8 Hz), 6.32 (2H, d, J = 6.8 Hz), 4.74 (1H, s), 3.73 (3H, s). 13C
NMR (CDCl3, 125 MHz, δ, TMS = 0): 174.49, 168.15, 162.04, 155.58, 150.77, 150.29, 145.86,
135.43, 130.54, 128.42, 127.78, 126.87, 125.54, 121.50, 117.56, 117.36, 115.84, 115.19, 112.27,
97.94, 55.90, 33.25. MS: m/z: 466 (M + H)+.
4.3.8.
1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(3-hydroxyphenyl)-6-oxo-7,10-dioxa]
anthracene (7a)
Yellowish brown solid; Yield: 89%, mp: 173-177ºC. 1H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.31 (1H, s), 7.52 (2H, d, J = 7.5 Hz), 7.11 (1H, m), 7.05 (2H, m), 6.97 (1H, m), 6.62 (1H, d, J =
7.1 Hz), 6.54 (1H, d, J = 7.0 Hz), 6.53 (1H, s), 6.50 (2H, d, J = 7.5 Hz), 6.35 (2H, d, J = 6.8 Hz),
13
4.70 (1H, s), 3.79 (3H, s). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 174.48, 168.19, 162.05,
158.42, 150.77, 150.24, 145.84, 136.57, 135.42, 130.11, 128.49, 126.84, 125.56, 121.77, 121.54,
117.36, 115.18, 114.74, 112.20, 97.92, 55.98, 33.54.MS: m/z: 466 (M + H)+.
4.3.9. 1,2-Benzo-[1,3-diaza-4-(4-methoxyanilisne)-5-(3,4-dihydroxyphenyl)-6-oxo-7,10-dioxa]
anthracene (8a)
1
Greenish yellow solid; Yield: 80%, mp: 164-168ºC. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.32 (1H, s), 7.43 (2H, d, J = 8.5 Hz), 7.10 (1H, m), 7.07 (2H, m), 6.58 (2H, d, J = 7.9 Hz), 6.45
(2H, d, J = 8.5 Hz), 6.41 (1H, d, J = 7.5 Hz), 6.36 (1H, s), 6.33 (2H, d, J = 6.9 Hz), 4.79 (1H, s),
3.81 (3H, s). 13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 174.35, 168.16, 162.05, 150.74, 150.35,
147.24, 145.89, 144.38, 135.47, 129.18, 128.45, 126.87, 125.51, 123.37, 121.56, 117.34, 117.25,
116.19, 115.18, 112.24, 97.94, 55.95, 33.60.MS: m/z: 482 (M + H)+.

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4.3.10. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(4-hydroxy-3-methoxyphenyl)-6-oxo-7,10-
dioxa]anthracene (9a)
1
Yellowish brown solid; Yield: 84%, mp: 165-169ºC. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.33 (1H, s), 7.48 (2H, d, J = 8.0 Hz), 7.17 (2H, m), 7.03 (3H, m), 6.54 (2H, d, J = 7.5 Hz), 6.50
(2H, d, J = 8.0 Hz), 6.41 (1H, d, J = 7.1 Hz), 6.40 (1H, s), 6.36 (2H, d, J = 7.0 Hz), 4.71 (1H, s),
3.61 (3H, s). 13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 174.49, 168.12, 162.04, 151.38, 150.74,
150.22, 145.87, 142.74, 135.46, 128.77, 128.44, 126.85, 125.54, 122.80, 121.53, 117.56, 117.32,
116.84, 115.18, 114.55, 112.20, 97.95, 56.24, 55.90, 33.55. MS: m/z: 496 (M + H)+.
4.3.11.
1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(3-methylphenyl)-6-oxo-7,10-dioxa]
anthracene (10a)
Reddish green solid; Yield: 83%, mp: 170-174ºC. 1H NMR (CDCl3, 500 MHz, δ, TMS = 0): 8.51
(1H, s), 7.56 (2H, d, J = 8.6 Hz), 7.32 (1H, s), 7.13 (1H, m), 7.06 (2H, m), 7.02 (1H, m), 6.87
(1H, m), 6.86 (1H, m), 6.85 (1H, s), 6.59 (2H, d, J = 8.6 Hz), 6.37 (2H, d, J = 7.6 Hz), 4.79 (1H,
s), 3.78 (3H, s), 2.35 (3H, s). 13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 174.40, 168.17, 162.05,
150.76, 150.24, 145.88, 138.32, 135.47, 135.06, 130.97, 128.64, 128.42, 126.84, 126.12, 125.52,
121.50, 117.52, 117.34, 115.12, 112.24, 97.90, 55.94, 33.54. MS: m/z: 464 (M + H)+.
4.3.12.
1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(4-fluorophenyl)-6-oxo-7,10-dioxa]
anthracene (11a)
Yellowish brown solid; Yield: 88%; mp: 186-190°C. 1H NMR (CDCl3 ,500 MHz , δ, TMS = 0):
8.74 (1H, s), 8.35 (1H, s), 8.00 (1H, d, J = 10 Hz), 7.54- 7.56 (1H, m), 7.71-7.75 (1H, m), 7.45-
7.49 (3H, m), 7.39 (2H, d, J = 5 Hz), 7.10-7.12 (2H, m), 6.88 (2H, d, J = 5 Hz), 5.64 (1H, s),
3.72 (3H, s). 13CNMR (CDCl3, 125 MHz, δ, TMS = 0): 168.30, 165.47, 165.00, 164.28, 161.80,
161.65, 161.07, 159.74, 157.34, 143.13, 143.11, 138.16, 136.94, 135.66, 135.59, 129.26, 129.22,
129.18, 127.87, 120.51, 120.32, 118.87, 118.58, 110.61, 103.21, 60.42, 37.51. MS: m/z: 468 (M
+ H)+.

ACCEPTED MANUSCRIPT
4.3.13.
1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(3-chlorophenyl)-6-oxo-7,10-
dioxa]anthracene (12a)
Yellowish brown solid; Yield: 82%; mp: 170-174°C.1H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.35 (1H, s), 8.00 (1H, s), 7.45-7.48 (3H, m), 7.36-7.39 (3H, m), 7.27-7.30 (3H, m), 6.88-6.90
13
(3H, m), 5.63 (1H, s), 3.72 (3H, s). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 165.62, 165.00,
164.34 161.96, 161.81, 161.15, 160.21, 160.01, 157.39, 149.16, 138.24, 138.07, 136.86, 135.65,
133.78, 132.62, 132.16, 130.13 129.38, 129.30, 127.94, 125.78, 121.85, 119.14, 118.90, 118.55,
110.10, 102.66, 60.50, 38.03, 29.00.MS: m/z: 484 (M + H)+.
4.3.14.
1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(4-chlorophenyl)-6-oxo-7,10-dioxa]
anthracene (13a)
1
Greenish brown solid; Yield: 89%, mp: 170-174°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.29 (1H, s), 7.53 (2H, d, J = 7.5 Hz), 7.09 (2H, d, J = 6.3 Hz), 7.07 (1H, m), 7.02 (2H, m), 7.00
(2H, d, J = 6.0 Hz), 6.59 (2H, d, J = 7.5 Hz), 6.23 (2H, m), 4.66 (1H, s), 3.63 (3H, s). 13C NMR
(CDCl3, 125 MHz, δ, TMS = 0): 174.46, 168.19, 162.24, 150.73, 150.24, 145.88, 135.47,
133.29, 131.31, 130.56, 128.85, 128.43, 126.83, 125.54, 121.52, 117.58, 117.34, 115.18, 97.94,
55.98, 33.26. MS: m/z: 484 (M + H)+.
4.3.15.
1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(4-bromophenyl)-6-oxo-7,10-
dioxa]anthracene (14a)
Yellowish brown solid; Yield: 74%, mp: 160-164°C. 1H NMR (CDCl3, 500 MHz, δ, TMS = 0): 8.46
(1H, s), 8.12 (1H, d, J = 6.9 Hz), 7.60 (1H, m), 7.49 (2H, d, J = 8.0 Hz), 7.32-7.40 (4H, m), 7.17 (2H,
m), 6.85 (2H, d, J = 8.0 Hz), 6.37 (1H, m), 5.04 (1H, s), 3.78 (3H, s). 13C NMR (CDCl3, 125 MHz, δ,
TMS = 0): 174.48, 168.11, 162.05, 150.77, 150.24, 145.80, 135.48, 134.19, 131.68, 131.33, 128.42,
126.85, 125.54, 121.58, 120.12, 117.54, 117.32, 115.11, 112.25, 97.98, 55.96, 33.26.MS: m/z: 529
(M + H)+.
4.3.16. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(3-nitrophenyl)-6-oxo-7,10-dioxa]anthracene
(15a)
1
Yellowish brown solid; Yield: 87%; mp: 170-174°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0): 8.52
(1H, s), 8.42 (1H, s), 8.19 (2H, m), 7.91 (1H, s), 7.68 (1H, m), 7.59 (1H, m), 7.45 (1H, m), 7.35 (1H,

ACCEPTED MANUSCRIPT
13
d, J = 10 Hz), 7.23 (2H, d, J = 10 Hz), 6.83 (2H, m), 6.52 (1H, s), 5.31 (1H, s), 3.85 (3H, s). C
NMR (CDCl3, 125 MHz, δ, TMS = 0): 174.42, 168.19, 162.04, 150.75, 150.29, 148.39, 145.86,
136.02, 135.49, 135.24, 129.60, 128.41, 126.82, 125.53, 124.37, 121.56, 118.13, 117.53, 117.34,
115.10, 112.25, 97.96, 55.97, 32.46. MS: m/z: 495 (M + H)+.
4.3.17. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(4-nitrophenyl)-6-oxo-7,10-dioxa]anthracene
(16a)
Yellowish brown solid; Yield: 81%, mp: 178-182°C. 1H NMR (CDCl3, 500 MHz, δ, TMS = 0): 8.49
(1H, s), 8.21 (2H, d, J = 8.7 Hz), 8.14 (1H, m), 7.69 (2H, d, J = 8.7 Hz), 7.33-7.45 (3H, m), 7.15
13
(2H, d, J = 8.4 Hz), 6.85 (2H, d, J = 12 Hz), 6.36 (1H, s), 5.23 (1H, s), 3.78 (3H, s). C NMR
(CDCl3, 125 MHz, δ, TMS = 0): 174.48, 168.19, 162.09, 150.79, 150.29, 145.86, 145.42, 141.29,
135.46, 130.00, 128.45, 126.87, 125.53, 121.56, 121.00, 117.55, 117.32, 115.19, 112.25, 97.95,
55.94, 33.96. MS: m/z: 495 (M + H)+.
4.3.18. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(thiophene)-6-oxo-7,10-dioxa]anthracene (17a)
Yellowish brown solid; Yield: 93%, mp: 160-164°C.1H NMR (CDCl3, 500 MHz , δ, TMS = 0): 8.51
(1H, s), 8.15 (1H, d, J = 5.00 Hz), 7.64 (2H, m), 7.34-7.49 (2H, m), 7.23 (2H, d, J = 10 Hz), 6.98-
7.07 (2H, m), 6.86 (2H, d, J = 10 Hz), 6.63 (1H, s), 5.51 (1H, s), 3.77 (3H, s). 13C NMR (CDCl3, 125
MHz, δ, TMS = 0): 174.48, 168.10, 162.00, 157.74, 150.29, 145.86, 139.49, 135.46, 128.44, 126.90,
126.85, 126.74, 125.50, 123.65, 121.58, 117.56, 117.32, 115.12, 112.24, 97.94, 55.98, 23.42.MS:
m/z: 456 (M + H)+.
4.3.19.
1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(pyridine-4-yl)-6-oxo-7,10-dioxa]anthracene
(18a)
1
Yellowish brown solid; Yield: 82%, mp: 160-164°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.46 (1H, s), 7.43 (2H, d, J = 8.0 Hz), 7.24 (3H, m), 7.11 (2H, m), 7.06 (2H, m), 6.63 (2H, d, J =
13
8.0 Hz), 6.31 (2H, m), 4.76 (1H, s), 3.71 (3H, s). C NMR (CDCl3, 125 MHz, δ, TMS = 0):
174.49, 168.11, 162.04, 150.78, 150.25, 149.98, 145.81, 146.53, 135.43, 128.42, 126.81, 125.51,
124.32, 121.59, 117.54, 117.39, 115.14, 112.29, 97.95, 55.94, 33.24. MS: m/z: 451 (M + H)+.

ACCEPTED MANUSCRIPT
4.3.20. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(indol-2-yl)-6-oxo-7,10-dioxa]anthracene
(19a)
1
Brown solid; Yield: 85%, mp: 172-176°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0): 8.32 (1H,
s), 7.44 (2H, d, J = 8.6 Hz), 7.29 (1H, s), 7.16 (1H, m), 7.08 (4H, m), 7.03 (2H, m), 6.58 (2H, d,
J = 8.6 Hz), 6.37 (2H, m), 6.13 (1H, s), 4.80 (1H, s), 3.76 (3H, s). 13C NMR (CDCl3, 125 MHz,
δ, TMS = 0): 174.48, 168.19, 162.00, 150.78, 150.24, 145.89, 136.69, 135.48, 135.26, 128.00,
128.47, 126.81, 125.54, 122.20, 121.58, 120.11, 119.00, 117.58, 117.34, 115.18, 112.24, 111.18,
101.66, 97.94, 55.98, 23.94. MS: m/z: 491 (M + H)+.
4.3.21.
1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(naphthyl)-6-oxo-7,10-dioxa]anthracene
(20a)
1
Brownish black solid; Yield: 83%, mp: 163-167°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.31 (1H, s), 7.77 (1H, m), 7.64 (1H, m), 7.51 (2H, d, J = 8.5 Hz), 7.31 (1H, m), 7.29 (1H, m),
7.26 (1H, m), 7.19 (1H, m), 7.12 (1H, m), 7.10 (1H, m), 7.02 (2H, m), 6.53 (2H, d, J = 8.5 Hz),
13
6.33 (2H, d, J = 7.1 Hz), 4.72 (1H, s), 3.66 (3H, s). C NMR (CDCl3, 125 MHz, δ, TMS = 0):
174.49, 168.10, 162.05, 150.75, 150.25, 145.89, 135.47, 135.26, 133.70, 131.82, 128.42, 128.09,
127.62, 127.54, 127.34, 127.00, 126.84, 126.00, 125.54, 125.11, 121.54, 117.52, 117.34, 115.18,
112.24, 97.94, 55.96, 33.64. MS: m/z: 500 (M + H)+.
4.3.22. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(phenyl)-10-oxa]anthracene (1b)
1
Brownish yellow solid; Yield: 78%, mp: 168-172°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.46 (1H, s), 8.13 (1H, d, J = 8.1 Hz), 7.53- 7.60 (5H, m), 7.43-7.49 (5H, m), 7.13 (2H, d, J = 8.7
13
Hz), 6.83 (2H, d, J = 8.7 Hz), 6.45 (1H, s), 5.05 (1H, s), 3.77 (3H, s). C NMR (CDCl3, 125
MHz, δ, TMS = 0): 172.86, 172.63, 151.80, 150.74, 150.28, 143.44, 135.47, 132.77, 129.30,
128.32, 127.44, 126.48, 126.39, 126.14, 125.73, 121.13, 120.25, 118.00, 117.38, 115.14, 55.94,
40.75. MS: m/z: 432 (M + H)+.
4.3.23. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(4-methoxyphenyl)-10-oxa]anthracene (2b)
1
Yellowish brown solid; Yield: 84%, mp: 164-168°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.49 (1H, s), 8.05 (1H, d, J = 8.6 Hz), 7.69 (1H, d, J = 8.4 Hz), 7.37 (1H, m), 7.31 (1H, m), 7.25
(1H, d, J = 8.0 Hz), 7.03 (1H, m), 6.95 (2H, m), 6.65 (4H, m), 6.52 (2H, d, J = 8.0 Hz), 5.39

ACCEPTED MANUSCRIPT
13
(1H, s), 3.76 (3H, s), 3.72 (3H, s). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 172.88, 172.64,
158.20, 151.87, 150.75, 150.24, 135.79, 135.48, 132.74, 129.32, 127.48, 126.44, 126.19, 125.75,
121.18, 120.22, 118.04, 117.35, 115.18, 114.84, 55.92, 40.77. MS: m/z: 462 (M + H)+.
4.3.24. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(2-methoxyphenyl)-10-oxa]anthracene (3b)
1
Brownish solid; Yield: 79%, mp: 171-174°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0): 8.37
(1H, s), 8.15 (1H, d, J = 7.8 Hz), 7.84 (1H, s), 7.59 (2H, d, J = 8.0 Hz), 7.44- 7.49 (4H, m), 7.28-
7.33 (5H, m), 6.59 (2H, d, J = 8.0 Hz), 5.52 (1H, s), 3.74 ( 3H, s), 3.71 (3H, s). 13C NMR
(CDCl3, 125 MHz, δ, TMS = 0): 172.80, 172.69, 157.98, 151.84, 150.77, 150.25, 135.49,
132.74, 129.36, 128.68, 127.45, 127.38, 126.42, 126.11, 125.75, 121.64, 121.19, 120.24, 118.09,
117.36, 115.12, 114.89, 103.56, 55.94, 56.28, 30.84. MS: m/z: 462 (M + H)+.
4.3.25. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(3,4-dimethoxyphenyl)-10-oxa]anthracene
(4b)
1
Yellowish brown solid; Yield: 68%, mp: 174-178°C. H NMR (CDCl3,500 MHz, δ, TMS = 0):
8.32 (1H, s), 8.09 (1H, d, J = 8.8 Hz), 7.69 (1H, d, J = 8.6 Hz), 7.39 (2H, m), 7.34 (1H, m), 7.21
(1H, d, J = 8.3 Hz), 7.06 (1H, d, J = 8.0 Hz), 6.54 (1H, d, J = 7.9 Hz), 6.48 (2H, d, J = 7.6 Hz),
6.46 (1H, d, J = 7.4 Hz), 6.43 (1H, d, J = 7.0 Hz), 6.35 (2H, d, J = 6.7 Hz), 5.34 (1H, s), 3.80
13
(3H, s), 3.76 (3H, s), 3.74 (3H, s). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 172.85, 172.64,
151.89, 150.74, 150.32, 150.24, 147.34, 136.75, 135.40, 132.77, 127.45, 126.48, 126.11, 125.74,
121.60, 121.11, 120.24, 118.00,117.32, 115.81, 115.14, 113.34, 103.56, 56.28, 55.90, 41.00. MS:
m/z: 492 (M + H)+.
4.3.26.
1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(3,4,5-trimethoxyphenyl)-10-oxa]
anthracene (5b)
1
Yellowish brown solid; Yield: 82%, mp: 165-169°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.43 (1H, s), 8.11 (1H, d, J = 8.4 Hz), 7.74 (2H, d, J = 8.5 Hz), 7.41 (1H, m), 7.37 (1H, m), 7.23
(1H, d, J = 8.0 Hz), 7.01 (1H, d, J = 7.6 Hz), 6.53 (2H, d, J = 8.5 Hz), 6.51 (2H, s), 6.37 (2H,
13
m), 5.38 (1H, s), 3.74 (3H, s), 3.71 (3H, s), 3.68 (3H, s), 3.63 (3H, s). C NMR (CDCl3, 125
MHz, δ, TMS = 0): 172.85, 172.64, 151.84, 151.34, 150.75, 137.77, 136.74, 135.42, 132.77,

ACCEPTED MANUSCRIPT
127.41, 126.42, 126.11, 125.74, 121.19, 120.20, 118.00, 117.34, 115.11, 56.94, 56.24, 55.98,
41.39. MS: m/z: 522 (M + H)+.
4.3.27. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(4-hydroxyphenyl)-10-oxa]anthracene (6b)
1
Greenish brown solid; Yield: 84%, mp: 173-177°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.49 (1H, s), 8.08 (1H, d, J = 7.9 Hz), 7.71 (1H, d, J = 7.7 Hz), 7.36 (1H, m), 7.31 (2H, m), 7.21
(1H, d, J = 7.3 Hz), 7.05 (1H, d, J = 7.0 Hz), 6.89 (2H, d, J = 6.7 Hz), 6.61 (2H, d, J = 9.0 Hz),
13
6.50 (2H, d, J = 6.3 Hz), 6.31 (2H, d, J = 6.1 Hz), 5.33 (1H, s), 3.78 (3H, s). C NMR (CDCl3,
125 MHz, δ, TMS = 0): 172.84, 172.60, 156.00, 151.84, 150.77, 150.26, 136.02, 135.47, 132.74,
129.78, 127.44, 126.42, 126.11, 125.79, 121.15, 120.25, 118.01, 117.33, 116.49, 115.18, 103.55,
55.99, 40.73. MS: m/z: 448 (M + H)+.
4.3.28. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(3-hydroxyphenyl)-10-oxa]anthracene (7b)
1
Yellowish brown solid; Yield: 82%, mp: 171-174°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.32 (1H, s), 8.04 (1H, d, J = 7.5 Hz), 7.67 (1H, m), 7.33 (2H, m), 7.28 (1H, m), 7.19 (1H, d, J =
7.1 Hz), 7.02 (1H, m), 6.61 (1H, d, J = 6.6 Hz), 6.57 (2H, d, J = 7.5 Hz), 6.53 (1H, s), 6.52 (2H,
d, J = 6.2 Hz), 6.37 (2H, d, J = 6.0 Hz), 5.39 (1H, s), 3.80 (3H, s). 13C NMR (CDCl3, 125 MHz,
δ, TMS = 0): 172.88, 172.65, 159.02, 151.89, 150.74, 150.20, 144.86, 135.40, 132.77, 130.78,
127.45, 126.44, 126.11, 125.75, 121.18, 120.96, 120.22, 118.05, 117.39, 115.11, 113.99, 113.45,
103.57, 55.98, 41.07. MS: m/z: 448 (M + H)+.
4.3.29. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(3,4-dihydroxyphenyl)-10-oxa]anthracene
(8b)
1
Yellowish brown solid; Yield: 86%, mp: 168-172°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.41 (1H, s), 8.07 (1H, d, J = 8.7 Hz), 7.69 (1H, d, J = 8.5 Hz), 7.39 (2H, m), 7.30 (2H, d, J =
8.0 Hz), 7.13 (1H, m), 7.00 (1H, d, J = 7.8 Hz), 6.52 (2H, d, J = 8.0 Hz), 6.45 (1H, d, J = 7.0
Hz), 6.44 (3H, m), 6.36 (1H, s), 5.32 (1H, s), 3.85 (3H, s). 13C NMR (CDCl3, 125 MHz, δ, TMS
= 0): 172.80, 172.65, 151.84, 150.74, 150.22, 147.88, 144.83, 137.42, 135.41, 132.77, 127.42,
126.44, 126.11, 125.78, 122.33, 121.18, 118.04, 117.89, 117.33, 115.32, 115.10, 103.55, 55.99,
41.07. MS: m/z: 464 (M + H)+.

ACCEPTED MANUSCRIPT
4.3.30.
1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(4-hydroxy-3-methoxyphenyl)-10-oxa]
anthracene (9b)
1
Greenish brown solid; Yield: 81%, mp: 162-166°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.31 (1H, s), 8.02 (1H, d, J = 7.8 Hz), 7.59 (1H, d, J = 7.4 Hz), 7.45 (2H, m), 7.34 (2H, d, J =
9.0 Hz), 7.19 (1H, m), 6.57 (2H, d, J = 9.0 Hz), 6.50 (1H, d, J = 7.0 Hz), 6.47 (1H, d, J = 7.0
13
Hz), 6.40 (1H, s), 6.27 (2H, m), 5.38 (1H, s), 3.75 (3H, s), 3.71 (3H, s). C NMR (CDCl3, 125
MHz, δ, TMS = 0): 172.88, 172.66, 151.99, 151.86, 150.75, 150.20, 143.29, 137.04, 135.42,
132.79, 127.48, 126.42, 126.11, 122.00, 121.18, 120.24, 118.04, 117.39, 115.18, 113.74, 103.55,
56.20, 55.98, 41.04. MS: m/z: 478 (M + H)+.
4.3.31. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(3-methylphenyl)-10-oxa]anthracene (10b)
1
Yellowish brown solid; Yield: 86%, mp: 167-171°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.33 (1H, s), 8.15 (1H, d, J = 8.2 Hz), 7.72 (1H, d, J = 7.9 Hz), 7.35 (2H, m), 7.25 (2H, d, J =
7.5 Hz), 7.05 (1H, d, J = 7.5 Hz), 7.02 (1H, m), 6.87 (2H, d, J = 7.0 Hz), 6.86 (1H, s), 6.52 (2H,
13
d, J = 7.5 Hz), 6.38 (2H, m), 5.39 (1H, s), 3.71 (3H, s), 2.30 (3H, s). C NMR (CDCl3, 125
MHz, δ, TMS = 0): 172.87, 172.65, 151.86, 150.74, 150.22, 143.34, 138.99, 135.44, 132.77,
130.11, 127.42, 126.64, 126.48, 126.11, 125.77, 125.38, 118.02, 117.34, 115.18, 103.54, 55.98,
41.04, 24.66. MS: m/z: 446 (M + H)+.
4.3.32. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(4-fluorophenyl)-10-oxa]anthracene (11b)
1
Yellowish brown solid; Yield: 82%, mp 169-172°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.51 (1H, s), 8.28-8.32 (2H, m), 7.92 (2H, m), 7.59-7.70 (2H, m), 7.31- 7.48 (7H, m), 6.87 (2H,
d, J = 9.0 Hz), 5.83 (1H, s), 3.71 (3H, s).13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 172.86,
172.65, 160.45, 151.83, 150.75, 150.28, 139.00, 135.41, 132.77, 129.98, 127.45, 126.43,
126.18,125.79, 121.11, 120.23, 118.04, 117.34, 116.00, 115.19, 103.56, 55.94, 40.75. MS: m/z:
450 (M + H)+.
4.3.33. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(3-chlorophenyl)-10-oxa]anthracene (12b)
1
Yellowish brown solid; Yield: 78%, mp: 165-169°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.49 (1H, s), 8.10 (1H, d, J = 8.0 Hz), 7.69 (1H, d, J = 7.9 Hz), 7.34 (1H, m), 7.30 (1H, m), 7.23
(2H, d, J = 8.5 Hz), 7.08 (2H, d, J = 7.5 Hz), 7.07 (1H, s), 7.03 (1H, d, J = 7.1 Hz), 6.90 (1H,

ACCEPTED MANUSCRIPT
13
m), 6.57 (2H, d, J = 8.5 Hz), 6.34 (2H, d, J = 8.0 Hz), 5.40 (1H, s), 3.67 (3H, s). C NMR
(CDCl3, 125 MHz, δ, TMS = 0): 172.86, 172.65, 151.84, 150.74, 150.26, 144.89, 135.49,
134.85, 132.79, 130.66, 128.19, 127.42, 126.43, 126.17, 125.78, 121.25, 120.25, 118.00, 117.34,
115.19, 103.56, 55.98, 40.25. MS: m/z: 466 (M + H)+.
4.3.34. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(4-chlorophenyl)-10-oxa]anthracene (13b)
Yellowish brown solid; Yield: 85%, mp: 161-165°C. 1H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.54 (1H, s), 7.78 (1H, d, J = 7.0 Hz), 7.51-7.64 (5H, m), 7.28 (1H, s), 7.11-7.17 (5H, m), 6.87
13
(2H, d, J = 9.0 Hz), 6.30 (1H, s), 5.22 (1H, s), 3.75 (3H, s). C NMR (CDCl3, 125 MHz, δ,
TMS = 0): 172.80, 172.65, 151.86, 150.75, 150.24, 141.57, 135.42, 132.76, 131.89, 129.77,
129.42, 127.48, 126.47, 126.12, 125.75, 121.18, 120.25, 118.00, 117.39, 115.19, 103.54, 55.92,
40.78. MS: m/z: 466 (M + H)+.
4.3.35. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(4-bromophenyl)-10-oxa]anthracene (14b)
Dark brown solid; Yield: 81%, mp: 178-180°C. 1H NMR (CDCl3, 500 MHz, δ, TMS = 0): 8.51
(1H, s), 8.28-8.32 (2H, m), 7.92 (2H, m), 7.59-7.70 (2H, m), 7.31- 7.48 (7H, m), 6.87 (2H, d, J =
9.0 Hz), 5.83 (1H, s), 3.71 (3H, s).13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 172.86, 172.64,
151.84, 150.79, 150.24, 140.25, 135.49, 132.74, 132.29, 130.55, 127.49, 126.43, 126.18, 125.70,
121.19, 120.65, 120.23, 118.00, 117.54, 117.34, 115.16, 103.54, 55.97, 40.78. MS: m/z: 510 (M
+ H)+.
4.3.36. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(3-nitrophenyl)-10-oxa]anthracene (15b)
Dark brown solid; Yield: 84%, mp: 175-178°C. 1H NMR (CDCl3, 500 MHz, δ, TMS = 0): 8.35
(1H, s), 8.12 (1H, d, J = 8.6 Hz), 8.00 (1H, d, J = 8.2 Hz), 7.99 (1H, s), 7.64 (1H, d, J = 7.7 Hz),
7.45 (1H, d, J = 7.5 Hz), 7.40 (2H, m), 7.31-7.34 (2H, m), 7.25 (1H, d, J = 7.3 Hz), 7.01 (1H,
13
m), 6.53 (2H, d, J = 7.5 Hz), 6.37 (2H, m), 5.34 (1H, s), 3.73 (3H, s). C NMR (CDCl3, 125
MHz, δ, TMS = 0): 172.85, 172.68, 151.84, 150.76, 150.25, 148.99, 135.49, 134.45, 132.78,
130.26, 127.46, 126.43, 126.11, 125.78, 121.11, 120.25, 118: C, .65, 118.00, 117.39, 115.15,
103.54, 55.97, 39.75. MS: m/z: 477 (M + H)+.

ACCEPTED MANUSCRIPT
4.3.37. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(4-nitrophenyl)-10-oxa]anthracene (16b)
1
Yellowish brown Semi-solid; Yield: 88%, mp: 175-179°C. H NMR (CDCl3, 500 MHz, δ, TMS
= 0): 8.49 (1H, s), 8.21 (2H, d, J = 8.5 Hz), 8.14 (1H, m), 7.69 (2H, d, J = 8.5 Hz), 7.33-7.45 (
5H, m), 7.15 (2H, d, J = 8 Hz), 6.41 (2H, d, J = 9.0 Hz), 6.36 (1H, s), 5.23 (1H, s), 3.78 (3H, s).
13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 174.49, 168.10, 162.00, 151.84, 150.74, 150.28,
149.50, 145.92, 145.81, 145.42, 141.26, 135.43, 132.75, 129.20, 127.48, 126.49, 126.10, 125.70,
121.65, 121.18, 120.24, 118.09, 117.34, 115.19, 103.54, 55.97, 40.75. MS: m/z: 477 (M + H)+.
4.3.38. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(thiophen-2-yl)-10-oxa]anthracene (17b)
1
Greenish brown solid; Yield: 82%, mp: 172-175°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.41 (1H, s), 8.01 (1H, d, J = 8.0 Hz), 7.68 (1H, m), 7.39 (1H, m), 7.36 (1H, m), 7.31 (2H, d, J =
7.5 Hz), 7.06 (1H, d, J = 7.0 Hz), 6.72 (2H, m), 6.60 (1H, m), 6.56 (2H, d, J = 7.5 Hz), 6.39 (2H,
13
d, J = 6.4 Hz), 5.36 (1H, s), 3.75 (3H, s). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 172.85,
172.64, 151.85, 150.78, 150.26, 139.48, 135.45, 132.76, 127.45, 126.91, 126.71, 126.44, 126.11,
125.78, 123.65, 121.15, 120.24, 118.04, 117.36, 115.11, 103.55, 55.94, 27.25. MS: m/z: 438 (M
+ H)+.
4.3.39. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(pyridin-4-yl)-10-oxa]anthracene (18b)
1
Yellowish brown solid; Yield: 86%, mp: 164-167°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.59 (2H, d, J = 8.3 Hz), 8.51 (1H, s), 8.05 (1H, d, J = 8.2 Hz), 7.76 (1H, d, J = 7.8 Hz), 7.44
(2H, m), 7.39 (1H, m), 7.30 (1H, d, J = 7.7 Hz), 7.23 (2H, d, J = 7.5 Hz), 7.04 (1H, m), 6.51
13
(2H, d, J = 7.5 Hz), 6.45 (2H, d, J = 6.9 Hz), 5.41 (1H, s), 3.61 (3H, s). C NMR (CDCl3, 125
MHz, δ, TMS = 0): 172.85, 172.63, 151.85, 150.76, 150.25, 149.98, 146.54, 135.42, 132.76,
127.45, 126.43, 126.1, 125.72, 124.38, 121.11, 120.25, 118.00, 117.34, 115.16, 103.55, 55.98,
40.75. MS: m/z: 433 (M + H)+.
4.3.40. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(indol-2-yl)-10-oxa]anthracene (19b)
1
Yellowish brown solid; Yield: 82%, mp: 167-169°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.41 (1H, s), 8.13 (1H, d, J = 8.5 Hz), 7.79 (1H, d, J = 8.2 Hz), 7.41 (1H, m), 7.37 (2H, m), 7.29
(2H, d, J = 7.0 Hz), 7.08 (4H, s), 7.01 (1H, m), 6.57 (2H, d, J = 7.0 Hz), 6.32 (2H, m), 6.21 (1H,
s), 5.31 (1H, s), 3.69 (3H, s). 13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 172.85, 172.66, 151.84,

ACCEPTED MANUSCRIPT
150.76, 136.68, 135.41, 135.22, 132.70, 128.00, 127.48, 126.45, 126.19, 125.75, 122.20, 121.18,
120.25, 119.05, 118.00, 117.35, 115.10, 111.12, 103.54, 101.65, 55.98, 25.74. MS: m/z: 471 (M
+ H)+.
4.3.41. 1,2-Benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(naphthyl)-10-oxa]anthracene (20b)
1
Yellowish brown solid; Yield: 85%, mp: 172-175°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.45 (1H, s), 8.01 (1H, d, J = 7.5 Hz), 7.77 (1H, d, J = 7.4 Hz), 7.69 (1H, d, J =7.3 Hz), 7.64
(1H, d, J = 7.1 Hz), 7.51 (1H, d, J = 7.0 Hz), 7.35 (1H, m), 7.32 (1H, m), 7.30 (1H, m), 7.29
(1H, m), 7.22 (2H, d, J = 8.5 Hz), 7.19 (1H, m), 7.10 (1H, m), 7.01 (1H, m), 6.51 (2H, d, J = 8.5
Hz), 6.30 (2H, d, J = 7.0 Hz), 5.25 (1H, s), 3.55 (3H, s). 13C NMR (CDCl3, 125 MHz, δ, TMS =
0): 172.80, 172.65, 151.82, 150.75, 150.25, 135.48, 135.28, 133.74, 132.75, 131.84, 128.00,
127.56, 127.34, 126.48, 126.13, 125.74, 125.11, 121.11, 120.23, 118.00, 117.34, 115.18, 103.52,
55.94, 41.18. MS: m/z: 482 (M + H)+.
4.3.42. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(phenyl)-4-oxa]anthracene (1c)
1
Brownish green solid; Yield: 78%; mp: 173-176°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.45 (1H, s), 8.15 (1H, d, J = 8.1 Hz), 7.52- 7.59 (5H, m), 7.42-7.45 (5H, m), 7.14 (2H, d, J = 8.7
13
Hz), 6.86 (2H, d, J = 8.7 Hz), 6.43 (1H, s), 5.07 (1H, s), 3.74 (3H, s). C NMR (CDCl3, 125
MHz, δ, TMS = 0): 173.98, 171.54, 151.80, 150.77, 143.44, 135.46, 133.58, 129.30, 128.86,
128.34, 126.32, 123.21, 122.50, 118.98, 117.34, 115.42, 115.11, 103.57, 55.96, 38.63. MS: m/z:
432 (M + H)+.
4.3.43. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(4-methoxyphenyl)-4-oxa]anthracene (2c)
1
Yellowish brown solid; Yield: 89%, mp: 168-172°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.45 (1H, s), 8.06 (1H, d, J = 8.6 Hz), 7.64 (1H, d, J = 8.4 Hz), 7.39 (1H, m), 7.36 (1H, m), 7.25
(1H, d, J = 8.0 Hz), 7.06 (1H, m), 6.93 (2H, m), 6.67 (4H, m), 6.55 (2H, d, J = 8.0 Hz), 5.36
13
(1H, s), 3.75 (3H, s), 3.72 (3H, s). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 173.98, 171.52,
158.20, 151.81, 150.74, 135.78, 132.56, 129.32, 128.88, 128.36, 126.34, 123.20, 122.21, 118.90,
117.37, 115.48, 115.19, 103.56, 55.92, 38.65. MS: m/z: 462 (M + H)+.

ACCEPTED MANUSCRIPT
4.3.44. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(2-methoxyphenyl)-4-oxa]anthracene (3c)
1
Brownish black solid; Yield: 81%, mp: 171-174°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.35 (1H, s), 8.16 (1H, d, J = 7.8 Hz), 7.85 (1H, s), 7.61 (2H, d, J = 8.0 Hz), 7.45-7.49 (4H, m),
13
7.23-7.27 (5H, m), 6.57 (2H, d, J = 8.0 Hz), 5.51 (1H, s), 3.73 (3H, s), 3.72 (3H, s). C NMR
(CDCl3, 125 MHz, δ, TMS = 0): 173.92, 171.58, 158.26, 153.74, 152.88, 150.71, 135.46,
133.53, 129.38, 128.84, 128.62, 128.31, 127.33, 126.35, 123.24, 122.58, 121.66, 118.91, 117.34,
115.41, 115.17, 114.89, 103.56, 56.23, 55.90, 34.78. MS: m/z: 462 (M + H)+.
4.3.45. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(3,4-dimethoxyphenyl)-4-oxa]anthracene
(4c)
1
Brownish yellow solid; Yield: 83%, mp: 174-178°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.34 (1H, s), 8.10 (1H, d, J = 8.8 Hz), 7.66 (1H, d, J = 8.6 Hz), 7.40 (2H, m), 7.36 (1H, m), 7.24
(1H, d, J = 8.3 Hz), 7.07 (1H, d, J = 8.0 Hz), 6.55 (1H, d, J = 7.9 Hz), 6.45 (2H, d, J = 7.6 Hz),
6.47 (1H, d, J = 7.4 Hz), 6.45 (1H, d, J = 7.0 Hz), 6.36 (2H, d, J = 6.7 Hz), 5.36 (1H, s), 3.81
13
(3H, s), 3.75 (3H, s), 3.72 (3H, s). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 174.94, 172.56,
157.23, 151.84, 150.36, 138.78, 135.42, 132.51, 128.32, 126.34, 123.34, 123.21, 122.56, 121.67,
118.99, 117.35, 115.48, 114.12, 103.55, 56.28, 38.60. MS: m/z: 492 (M + H)+.
4.3.46.
1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(3,4,5-triimethoxyphenyl)-4-
oxa]anthracene (5c)
1
Brownish green solid; Yield: 87%, mp: 173-176°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.42 (1H, s), 8.14 (1H, d, J = 8.4 Hz), 7.75 (2H, d, J = 8.5 Hz), 7.43 (1H, m), 7.38 (1H, m), 7.24
(1H, d, J = 8.0 Hz), 7.03 (1H, d, J = 7.6 Hz), 6.55 (2H, d, J = 8.5 Hz), 6.54 (2H, s), 6.38 (2H,
13
m), 5.39 (1H, s), 3.73 (3H, s), 3.72 (3H, s), 3.69 (3H, s), 3.62 (3H, s). C NMR (CDCl3, 125
MHz, δ, TMS = 0): 174.51, 171.58, 153.76, 151.84, 151.39, 150.76, 137.77 136.77, 135.42,
132.56, 128.88, 128.38, 126.32, 123.25, 122.58, 118.99, 117.35, 115.44, 115.10, 103.57, 56.23,
39.28. MS: m/z: 522 (M + H)+.
4.3.47. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(4-hydroxyphenyl)-4-oxa]anthracene (6c)
1
Brownish black solid; Yield: 82%, mp 171-174°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.47 (1H, s), 8.08 (1H, d, J = 7.9 Hz), 7.71 (1H, d, J = 7.7 Hz), 7.39 (1H, m), 7.34 (2H, m), 7.26

ACCEPTED MANUSCRIPT
(1H, d, J = 7.3 Hz), 7.05 (1H, d, J = 7.0 Hz), 6.90 (2H, d, J = 6.7 Hz), 6.62 (2H, d, J = 9.0 Hz),
13
6.51 (2H, d, J = 6.3 Hz), 6.34 (2H, d, J = 6.1 Hz), 5.35 (1H, s), 3.73 (3H, s). C NMR (CDCl3,
125 MHz, δ, TMS = 0): 173.92, 171.54, 156.00, 153.78, 151.84, 150.72, 136.00, 135.47, 133.59,
129.75, 128.82, 128.34, 123.20, 122.54, 118.90, 117.32, 116.44, 115.18, 103.55, 55.94, 38.62.
MS: m/z: 448 (M + H)+.
4.3.48. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(3-hydroxyphenyl)-4-oxa]anthracene (7c)
1
Yellowish brown solid; Yield: 79%, mp: 169-173°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.35 (1H, s), 8.05 (1H, d, J = 7.5 Hz), 7.64 (1H, m), 7.35 (2H, m), 7.29 (1H, m), 7.21 (1H, d, J =
7.1 Hz), 7.04 (1H, m), 6.65 (1H, d, J = 6.6 Hz), 6.58 (2H, d, J = 7.5 Hz), 6.52 (1H, s), 6.50 (2H,
d, J = 6.2 Hz), 6.38 (2H, d, J = 6.0 Hz), 5.41 (1H, s), 3.80 (3H, s). 13C NMR (CDCl3, 125 MHz,
δ, TMS = 0): 173.94, 171.58, 159.00, 1523.74, 151.74, 150.78, 144.82, 135.42, 130.74, 133.59,
128.84, 128.32, 126.35, 122.52, 120.94, 117.38, 115.42, 115.11, 113.40, 103.54, 55.98, 38.97.
MS: m/z: 448 (M + H)+.
4.3.49. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(3,4--dihydroxyphenyl)-4-oxa]anthracene
(8c)
1
Brownish green solid; Yield: 85%, mp: 172-176°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.43 (1H, s), 8.08 (1H, d, J = 8.7 Hz), 7.66 (1H, d, J = 8.5 Hz), 7.42 (2H, m), 7.31 (2H, d, J =
8.0 Hz), 7.14 (1H, m), 7.02 (1H, d, J = 7.8 Hz), 6.51 (2H, d, J = 8.0 Hz), 6.46 (1H, d, J = 7.0
Hz), 6.45 (3H, m), 6.34 (1H, s), 5.31 (1H, s), 3.73 (3H, s). 13C NMR (CDCl3, 125 MHz, δ, TMS
= 0): 173.98, 171.54, 153.72, 151.00, 150.74, 147.85, 144.82, 137.41, 135.42, 133.50, 128.80,
128.32, 126.34, 123.24, 122.58, 122.30, 118.92, 117.88, 117.32, 115.10, 103.54, 55.94, 38.92.
MS: m/z: 464 (M + H)+.
4.3.50.
1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(4-hydroxy-3-methoxyphenyl)-4-oxa]
anthracene (9c)
1
Brownish yellow solid; Yield: 84%, mp: 171-174°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.33 (1H, s), 8.05 (1H, d, J = 7.8 Hz), 7.60 (1H, d, J = 7.4 Hz), 7.46 (2H, m), 7.32 (2H, d, J =
9.0 Hz), 7.23 (1H, m), 6.58 (2H, d, J = 9.0 Hz), 6.53 (1H, d, J = 7.0 Hz), 6.48 (1H, d, J = 7.0
Hz), 6.41 (1H, s), 6.28 (2H, m), 5.39 (1H, s), 3.74 (3H, s), 3.71 (3H, s). 13C NMR (CDCl3, 125

ACCEPTED MANUSCRIPT
MHz, δ, TMS = 0): 173.95, 171.52, 153.74, 151.90, 151.00, 150.75, 143.25, 137.00, 135.42,
133.55, 128.85, 128.39, 126.32, 122.50, 122.09, 117.46, 117.35, 115.45, 115.12, 103.57, 56.28,
55.95, 38.96. MS: m/z: 478 (M + H)+.
4.3.51. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(3-methylphenyl)-4-oxa]anthracene (10c)
1
Yellowish brown solid; Yield: 76%, mp: 162-166°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.35 (1H, s), 8.17 (1H, d, J = 8.2 Hz), 7.71 (1H, d, J = 7.9 Hz), 7.37 (2H, m), 7.24 (2H, d, J =
7.5 Hz), 7.06 (1H, d, J = 7.5 Hz), 7.03 (1H, m), 6.87 (2H, d, J = 7.0 Hz), 6.84 (1H, s), 6.55 (2H,
13
d, J = 7.5 Hz), 6.36 (2H, m), 5.36 (1H, s), 3.72 (3H, s), 2.30 (3H, s). C NMR (CDCl3, 125
MHz, δ, TMS = 0): 173.94, 171.58, 153.78, 151.86, 150.74, 143.34, 138.95, 135.47, 133.54,
129.20, 128.85, 128.30, 126.65, 126.34, 125.32, 122.56, 118.94, 117.35, 115.42, 115.18, 103.54,
55.96, 38.92, 24.68. MS: m/z: 446 (M + H)+.
4.3.52. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(4-florophenyl)-4-oxa]anthracene (11c)
1
Yellowish brown solid; Yield: 85%, mp: 165-168°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.52 (1H, s), 8.24-8.30 (2H, m), 7.93 (2H, m), 7.68-7.73 (2H, m), 7.33- 7.40 (7H, m), 6.88 (2H,
13
d, J = 9.0 Hz), 5.84 (1H, s), 3.71 (3H, s). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 173.90,
171.58, 160.42, 153.76, 151.84, 150.72, 139.02, 135.54, 133.54, 129.90, 128.86, 128.34, 126.35,
123.25, 122.00, 118.91, 117.34, 116.00, 115.48, 115.16, 103.56, 55.94, 38.60. MS: m/z: 450 (M
+ H)+.
4.3.53. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(3-chlorophenyl)-4-oxa]anthracene (12c)
1
Yellowish brown solid, Yield: 79%, mp: 166-169°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.48 (1H, s), 8.11 (1H, d, J = 8.0 Hz), 7.67 (1H, d, J = 7.9 Hz), 7.35 (1H, m), 7.32 (1H, m), 7.25
(2H, d, J = 8.5 Hz), 7.09 (2H, d, J = 7.5 Hz), 7.06 (1H, s), 7.05 (1H, d, J = 7.1 Hz), 6.92 (1H,
13
m), 6.55 (2H, d, J = 8.5 Hz), 6.36 (2H, d, J = 8.0 Hz), 5.43 (1H, s), 3.72 (3H, s). C NMR
(CDCl3, 125 MHz, δ, TMS = 0): 173.92, 171.54, 153.74, 151.85, 150.75, 144.89, 135.42,
134.86, 133.59, 130.75, 128.84, 128.35, 126.48, 126.32, 123.21, 122.54, 118.93, 17.32, 115.19,
103.56, 55.94, 38.12. MS: m/z: 466 (M + H)+.

ACCEPTED MANUSCRIPT
4.3.54. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(4-chlorophenyl)-4-oxa]anthracene (13c)
1
Brownish green solid; Yield: 82%, mp: 169-173°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.54 (1H, s), 7.75 (1H, d, J = 7.0 Hz), 7.50-7.60 (5H, m), 7.25 (1H, s), 7.12-7.17 (5H, m), 6.88
13
(2H, d, J = 9.0 Hz), 6.33 (1H, s), 5.26 (1H, s), 3.74 (3H, s). C NMR (CDCl3, 125 MHz, δ,
TMS = 0): 173.92, 171.54, 153.72, 151.84, 150.76, 141.53, 135.46, 133.59, 131.84, 129.78,
129.41, 128.88, 128.32, 126.34, 122.58, 118.93, 117.36, 115.45, 115.18, 103.57, 55.98, 38.64.
MS: m/z: 466 (M + H)+.
4.3.55. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(4-bromophenyl)-4-oxa]anthracene (14c)
1
Brownish yellow solid; Yield: 84%, mp: 170-173°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.53 (1H, s), 8.27-8.32 (2H, m), 7.91 (2H, m), 7.58-7.61 (2H, m), 7.32-7.41 (7H, m), 6.88 (2H, d,
J = 9.0 Hz), 5.84 (1H, s), 3.73 (3H, s). 13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 173.94,
171.56, 153.74, 151.82, 150.76, 142.49, 135.46, 133.52, 132.29, 130.56, 128.84, 128.32, 126.35,
123.21, 122.54, 120.61, 118.95, 117.35, 115.18, 103.52, 55.96. MS: m/z: 510 (M + H)+.
4.3.56. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(3-nitrophenyl)-4-oxa]anthracene (15c)
1
Brownish yellow solid; Yield: 87%, mp: 173-176°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.37 (1H, s), 8.14 (1H, d, J = 8.6 Hz), 8.01 (1H, d, J = 8.2 Hz), 7.98 (1H, s), 7.65 (1H, d, J = 7.7
Hz), 7.44 (1H, d, J = 7.5 Hz), 7.43 (2H, m), 7.32-7.35 (2H, m), 7.27 (1H, d, J = 7.3 Hz), 7.02
13
(1H, m), 6.54 (2H, d, J = 7.5 Hz), 6.38 (2H, m), 5.32 (1H, s), 3.73 (3H, s). C NMR (CDCl3,
125 MHz, δ, TMS = 0): 173.94, 171.58, 153.74, 151.80, 150.76, 148.94, 144.39, 135.46, 134.48,
133.59, 130.21, 128.85, 128.32, 126.35, 123.24, 122.51, 118.94, 118.65, 117.39, 115.10, 103.52,
55.92, 37.64. MS: m/z: 477 (M + H)+.
4.3.57. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(4-nitrophenyl)-4-oxa]anthracene (16c)
1
Yellowish brown solid; Yield: 74%, mp: 167-171°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.51 (1H, s), 8.23 (2H, d, J = 8.5 Hz), 8.15 (1H, m), 7.70 (2H, d, J = 8.5 Hz), 7.34-7.44 ( 5H, m),
13
7.16 (2H, d, J = 8 Hz), 6.43 (2H, d, J = 9.0 Hz), 6.36 (1H, s), 5.23 (1H, s), 3.73 (3H, s). C
NMR (CDCl3, 125 MHz, δ, TMS = 0): 174.49, 172.83, 155.62, 151.58, 150.73, 149.58, 146.83,
135.73, 133.63, 129.93, 127.98, 126.84, 125.36, 123.25, 122.47, 121.84, 118.83, 117.83, 115.73,
115.36, 102.64, 57.94, 38.93. MS: m/z: 477 (M + H)+.

ACCEPTED MANUSCRIPT
4.3.58. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(thiophene)-4-oxa]anthracene (17c)
1
Brownish yellow solid; Yield: 82%, mp: 165-169°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.43 (1H, s), 8.04 (1H, d, J = 8.0 Hz), 7.69 (1H, m), 7.43 (1H, m), 7.37 (1H, m), 7.33 (2H, d, J =
7.5 Hz), 7.05 (1H, d, J = 7.0 Hz), 6.74 (2H, m), 6.63 (1H, m), 6.53 (2H, d, J = 7.5 Hz), 6.40 (2H,
13
d, J = 6.4 Hz), 5.38 (1H, s), 3.76 (3H, s). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 174.83,
172.83, 153.74, 151.83, 150.63, 139.47, 136.71, 133.52, 128.94, 128.01, 126.92, 126.11, 126.03,
123.26, 123.08, 122.52, 118.95, 117.97, 114.62, 114.13, 102.73, 54.85, 25.14. MS: m/z: 438 (M
+ H)+.
4.3.59. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(pyridine)-4-oxa]anthracene (18c)
1
Brownish yellow solid; Yield: 86%, mp: 173-176°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.61 (2H, d, J = 8.3 Hz), 8.52 (1H, s), 8.07 (1H, d, J = 8.2 Hz), 7.73 (1H, d, J = 7.8 Hz), 7.45
(2H, m), 7.40 (1H, m), 7.34 (1H, d, J = 7.7 Hz), 7.22 (2H, d, J = 7.5 Hz), 7.03 (1H, m), 6.54
13
(2H, d, J = 7.5 Hz), 6.46 (2H, d, J = 6.9 Hz), 5.43 (1H, s), 3.73 (3H, s). C NMR (CDCl3, 125
MHz, δ, TMS = 0): 173.52, 171.83, 153.06, 151.58, 150.84, 149.94, 146.89, 135.73, 133.52,
128.84, 128.27, 126.12, 124.13, 123.47, 122.46, 118.94, 116.73, 114.62, 114.13, 103.82, 55.82,
38.93. MS: m/z: 433 (M + H)+.
4.3.60. 1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(indole)-4-oxa]anthracene (19c)
1
Brownish black solid; Yield: 82%, mp: 172-176°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.44 (1H, s), 8.12 (1H, d, J = 8.5 Hz), 7.81 (1H, d, J = 8.2 Hz), 7.43 (1H, m), 7.40 (2H, m), 7.32
(2H, d, J = 7.0 Hz), 7.10 (4H, s), 7.03 (1H, m), 6.56 (2H, d, J = 7.0 Hz), 6.33 (2H, m), 6.23 (1H,
s), 5.33 (1H, s), 3.70 (3H, s). 13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 173.85, 172.94, 154.82,
152.96, 150.72, 140.17, 136.72, 134.82, 131.84, 130.97, 128.84, 128.12, 126.90, 123.93, 121.35,
118.84, 117.37, 115.47, 114.26, 110.57, 108.47, 103.63, 55.27, 25.26, 25.02. MS: m/z: 471 (M +
H)+.
4.3.61. .1,2-Benzo-[1,3-diaza-10-(4-methoxyaniline)-9-(naphthyl)-4-oxa]anthracene (20c)
1
Brownish yellow solid; Yield: 85%, mp: 174-178°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.43 (1H, s), 8.03 (1H, d, J = 7.5 Hz), 7.75 (1H, d, J = 7.4 Hz), 7.73 (1H, d, J =7.3 Hz), 7.63
(1H, d, J = 7.1 Hz), 7.51 (1H, d, J = 7.0 Hz), 7.38 (1H, m), 7.34 (1H, m), 7.29 (2H, m), 7.23

ACCEPTED MANUSCRIPT
(2H, d, J = 8.5 Hz), 7.19 (1H, m), 7.11 (1H, m), 7.03 (1H, m), 6.55 (2H, d, J = 8.5 Hz), 6.31
(2H, d, J = 7.0 Hz), 5.26 (1H, s), 3.73 (3H, s). 13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 175.25,
117.94, 163.68, 151.84, 150.41, 136.83, 134.62, 132.58, 132.15, 128.38, 128.13, 126.73, 126.36,
126.19, 125.58, 124.57, 124.10, 123.74, 122.63, 118.47, 117.47, 115.32, 115.28, 103.57, 55.47,
36.93. MS: m/z: 482 (M + H)+.
4.3.62. 4-(4-methoxyaniline)-5-(phenyl)-8,9-dihydro-5H-chromeno[2,3-d]pyrimidin-6(7H)-one
(1d)
1
Greenish brown solid; Yield: 81%, mp: 182-186°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.34 (1H, s), 7.51 (2H, m), 7.31 (2H, d, J = 7.5 Hz), 7.07 (1H, m), 7.06 (2H, d, J = 7.1 Hz), 6.51
(2H, d, J = 7.5 Hz), 6.34 (1H, m), 4.73 (1H, s), 3.71 (3H, s), 2.98 (2H, m), 2.01 (2H, m), 1.46
13
(2H, m). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 198.95, 175.54, 167.02, 161.27, 150.79,
145.86, 135.41, 135.12, 129.17, 128.72, 125.83, 117.34, 115.18, 112.23, 109.83, 55.97, 36.73,
32.14, 28.65, 19.24. MS: m/z: 399 (M + H)+.
4.3.63. 4-(4-methoxyaniline)-5-(4-methoxyphenyl)-8,9-dihydro-5H-chromeno[2,3-d]pyrimidin-
6(7H)-one (2d)
Reddish brown solid; Yield: 83%, mp 184-188°C. 1H NMR (CDCl3 , 500 MHz, δ, TMS = 0):
8.35 (1H, s), 7.45 (2H, d, J = 7.5 Hz), 7.31 (2H, d, J = 8.5 Hz), 6.53 (2H, d, J = 8.5 Hz), 6.33
(2H, d, J = 7.5 Hz), 4.72 (1H, s), 3.72 (3H, s), 3.69 (3H, s), 2.93 (2H, m), 1.95 (2H, m), 1.45
13
(2H, m). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 197.90, 173.67, 166.03, 162.25, 153.75,
149.73, 143.67, 139.43, 128.23, 126.34, 116.34, 114.24, 112.23, 110.26, 108.45, 53.67, 35.73,
31.15, 26.23, 17.34. MS: m/z: 430 (M + H)+.
4.3.64. 4-(4-methoxyaniline)-5-(2-methoxyphenyl)-8,9-dihydro-5H-chromeno[2,3-d]pyrimidin-
6(7H)-one (3d)
Dark brown solid; Yield: 89%, mp: 192-195°C. 1H NMR (CDCl3, 500 MHz, δ, TMS = 0): 8.43
(1H, s), 7.35 (2H, d, 8.0 Hz), 6.95 (1H, d, J = 6.9 Hz), 6.70 (1H, m), 6.67 (1H, d, J = 7.0 Hz),
6.54 (2H, d, J = 8.0 Hz), 6.30 (2H, d, J = 7.5 Hz), 4.70 (1H, s), 3.68 (3H, s), 3.65 (3H, s), 2.91
(2H, m), 1.98 (2H, m), 1.46 (2H, m). 13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 196.76, 175.34,

ACCEPTED MANUSCRIPT
165.04, 160.21, 157.73, 148.38, 142.86, 133.42, 129.14, 125.86, 121.08, 117.54, 114.1, 112.35,
111.34, 109.85, 57.89, 54.97, 35.73, 28.63, 21.25, 18.56. MS: m/z: 430 (M + H)+.
4.3.65.
4-(4-methoxyaniline)-5-(3,4-dimethoxyphenyl)-8,9-dihydro-5H-chromeno[2,3-
d]pyrimidin-6(7H)-one (4d)
Brownish green solid; Yield: 83%, mp: 191-195°C. 1H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.45 (1H, s), 7.45 (2H, d, J = 8.5 Hz), 7.28 (1H, s), 7.08-7.11 (1H, m), 6.51 (2H, d, J = 8.5 Hz),
6.27 (2H, d, J = 7.4 Hz), 4.77 (1H, s), 3.73 (3H, s), 3.71 (3H, s), 3.68 (3H, s), 2.89 (2H, m), 1.97
(2H, m), 1.48 (2H, m). 13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 196.78, 177.46, 169.07,
163.35, 152.65, 148.73, 145.87, 144.54, 135.43, 128.47, 122.45, 117.36, 116.34, 115.23, 114.13,
111.34, 109.76, 56.78, 54.78, 35.76, 32.56, 28.56, 18.56. MS: m/z: 460 (M + H)+.
4.3.66.
4-(4-methoxyaniline)-5-(3,4,5-trimethoxyphenyl)-8,9-dihydro-5H-chromeno[2,3-
d]pyrimidin-6(7H)-one (5d)
Yellowish brown solid; Yield: 76%, mp: 196-199°C. 1H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.38 (1H, s), 7.41 (2H, d, J = 9.5 Hz), 6.55 (2H, d, J = 9.5 Hz), 6.37 (2H, s), 4.78 (1H, s), 3.75
13
(3H, s), 3.74 (3H, s), 3.72 (3H, s), 3.69 (3H, s), 2.90 (2H, m), 1.99 (2H, m), 1.43 (2H, m). C
NMR (CDCl3, 125 MHz, δ, TMS = 0): 199.34, 179.45, 168.05, 164.38, 156.56, 146.56, 136.25,
135.34, 129.47, 118.34, 116.23, 111.32, 107.85, 106.47, 56.53, 56.25, 55.97, 36.75, 32.75, 29.54,
18.34. MS: m/z: 490 (M + H)+.
4.3.67. 4-(4-methoxyaniline)-5-(4-hydroxyphenyl)-8,9-dihydro-5H-chromeno[2,3-d]pyrimidin-
6(7H)-one (6d)
Brown solid; Yield: 83%, mp: 181-184°C. 1H NMR (CDCl3, 500 MHz , δ, TMS = 0): 8.35 (1H,
s), 7.85-7.88 (2H, d, J = 8.5 Hz), 7.43 (2H, d, J = 8.0 Hz), 6.99-7.03 (2H, d, J = 8.5 Hz), 6.59
(2H, m), 6.53 (2H, d, J = 8.0 Hz), 4.76 (1H, s), 3.75 (3H, s), 2.93 (2H, m), 1.95 (2H, m), 1.47
13
(2H, m). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 196.67, 174.67, 165.07, 160.45, 156.76,
150.45, 143.87, 135.46, 129.57, 127.78, 116.45, 114.83, 113.41, 110.34, 107.84, 54.96, 36.79,
31.17, 25.64, 17.39. MS: m/z: 416 (M + H)+.

ACCEPTED MANUSCRIPT
4.3.68. 4-(4-methoxyaniline)-5-(3-hydroxyphenyl)-8,9-dihydro-5H-chromeno[2,3-d]pyrimidin-
6(7H)-one (7d)
Yellowish brown solid; Yield: 72%, mp: 184-187°C. 1H NMR (CDCl3,500 MHz, δ, TMS = 0):
8.44 (1H, s), 7.85 (1H, m), 7.50-7.53 (3H, m), 7.45 (2H, d, J = 8.0 Hz), 6.54 (2H, d, J = 8.0 Hz),
6.38 (2H, d, J = 7.2 Hz), 4.73 (1H, s), 3.77 (3H, s), 2.91 (2H, m), 1.97 (2H, m), 1.41 (2H, m).
13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 199.64, 173.59, 164.97, 159.56, 156.87, 150.57,
145.45, 135.56, 133.56, 130.13, 121.54, 115.56, 114.56, 112.74, 110.67, 109.34, 106.39, 53.76,
36.73, 32.49, 27.62, 15.28. MS: m/z: 416 (M + H)+.
4.3.69.
4-(4-methoxyaniline)-5-(3,4-dihydroxyphenyl)-8,9-dihydro-5H-chromeno[2,3-
d]pyrimidin-6(7H)-one (8d)
Yellow solid; Yield: 82%, mp: 184-187°C. 1H NMR (CDCl3, 500 MHz, δ, TMS = 0): 8.32 (1H,
s), 7.47 (2H, m), 7.39-7.42 (2H, m), 7.02-7.03 (1H, m), 6.54 (2H, d, J = 8.0 Hz), 6.36 (1H, s),
13
6.32 (2H, m), 4.76 (1H, s), 3.79 (3H, s), 2.89 (2H, m), 1.89 (2H, m), 1.37 (2H, m). C NMR
(CDCl3, 125 MHz, δ, TMS = 0): 199.58, 174.67, 165.07, 160.34, 152.73, 147.25, 145.86,
144.37, 135.46, 129.15, 123.13, 117.35, 117.21, 116.12, 114.14, 111.25, 108.65, 53.97, 32.43,
30.42, 27.43, 15.32. MS: m/z: 432 (M + H)+.
4.3.70.
4-(4-methoxyaniline)-5-(4-hydroxy-3-methoxyphenyl)-8,9-dihydro-5H-chromeno[2,3-
d]pyrimidin-6(7H)-one (9d)
1
Greenish brown solid; Yield: 84%, mp: 190-194°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.39 (1H, s), 7.28 (1H, s), 7.16 (2H, d, J = 10 Hz), 6.84-6.92 (5H, m), 6.52 (1H, s), 4.86 (1H, s),
3.85 (3H, s), 3.78 (3H, s), 2.76 (2H, m), 2.43 (2H, m), 2.05-2.08 (2H, m). 13C NMR (CDCl3, 125
MHz, δ, TMS = 0): 196.35, 164.93, 161.15, 159.90, 156.89, 147.08, 145.29, 139.27, 133.57,
130.93, 124.46, 123.71, 121.59, 115.66, 114.88, 114.21, 111.08, 98.49, 56.06, 55.49, 36.86,
30.30, 27.58, 20.10. MS: m/z: 446 (M + H)+.
4.3.71.
4-(4-methoxyaniline)-5-(3-methylphenyl)-8,9-dihydro-5H-chromeno[2,3-d]pyrimidin-
6(7H)-one (10d)
Reddish brown solid; Yield: 80%, mp: 193-196°C. 1H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.45 (1H, s), 7.86 (1H, m), 7.52-7.55 (3H, m), 7.41 (2H, d, J = 8.0 Hz), 6.55 (2H, d, J = 8.0 Hz),

ACCEPTED MANUSCRIPT
6.39 (1H, m), 4.66 (1H, s), 3.69 (3H, s), 2.91 (2H, m), 2.35 (3H, s), 1.86 (2H, m), 1.39 (2H, m).
13C NMR (CDCl3, 125 MHz, δ, TMS = 0): 200.56, 177.52, 168.36, 163.35, 156.73, 147.84,
138.35, 135.46, 135.05, 130.97, 128.64, 126.14, 116.35, 115.15, 113.45, 109.67, 56.96, 38.47,
34.58, 29.63, 24.68, 17.26. MS: m/z: 414 (M + H)+.
4.3.72.
4-(4-methoxyaniline)-5-(4-fluorophenyl)-8,9-dihydro-5H-chromeno[2,3-d]pyrimidin-
6(7H)-one (11d)
Yellowish brown solid; Yield: 83%, mp: 192-195°C. 1H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.38 (1H, s), 7.94-7.99 (2H, d, J = 7.5 Hz), 7.55-7.58 (2H, d, J = 7.5 Hz), 7.43-7.49 (2H, d, J =
8.5 Hz), 6.52 (2H, d, J = 8.5 Hz), 4.69 (1H, s), 3.70 (3H, s), 2.97 (2H, m), 1.93 (2H, m), 1.47
13
(2H, m). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 198.34, 174.52, 165.04, 162.39, 159.94,
152.73, 147.63, 134.73, 130.71, 119.51, 115.48, 115.13, 112.26, 109.83, 57.47, 37.84, 32.14,
26.47, 14.48. MS: m/z: 418 (M + H)+.
4.3.73.
4-(4-methoxyaniline)-5-(3-chlorophenyl)-8,9-dihydro-5H-chromeno[2,3-d]pyrimidin-
6(7H)-one (12d)
1
Brownish yellow solid; Yield: 73%, mp: 184-187°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.48 (1H, s), 8.16 (1H, s), 7.49 (1H, s), 7.17-7.22 (2H, m), 7.11(1H, d, J = 5 Hz), 6.78 (2H, d, J =
13
5 Hz), 5.37 (1H, s), 3.71 (3H, s), 2.65-2.76 (2H, m), 2.33-2.35 (2H, m), 1.94-2.05 (2H, m). C
NMR (CDCl3, 125 MHz, δ, TMS = 0): 196.02, 166.03, 161.62, 159.60, 156.35, 156.23, 145.62,
133.45, 132.12, 130.09, 128.65, 127.04, 126.64, 124.54, 115.63, 113.73, 98.55, 55.44, 36.86,
31.55, 27.44, 20.28. MS: m/z: 434 (M + H)+.
4.3.74.
4-(4-methoxyaniline)-5-(4-chlorophenyl)-8,9-dihydro-5H-chromeno[2,3-d]pyrimidin-
6(7H)-one (13d)
1
Brownish yellow solid; Yield 83%, mp: 189-193°C. H NMR (CDCl3, 500 MHz, δ, TMS = 0):
8.41 (1H, s), 7.96-8.01 (2H, d, J = 7.5 Hz), 7.56-7.59 (2H, d, J = 7.5 Hz), 7.45-7.49 (2H, d, J =
8.5 Hz), 6.49 (2H, d, J = 8.5 Hz), 4.69 (1H, s), 3.70 (3H, s), 2.97 (2H, m), 1.93 (2H, m), 1.47
13
(2H, m). C NMR (CDCl3, 125 MHz, δ, TMS = 0): 194.56, 173.63, 167.04, 162.45, 153.95,
146.52, 135.42, 133.52, 131.36, 130.42, 127.85, 116.53, 114.31, 111.46, 105.42, 58.73, 37.53,
36.92, 24.63, 14.58. MS: m/z: 434 (M + H)+.