Hydroxyapatite nanoparticles (HAP NPs): A green and efficient heterogeneous catalyst for three-component one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media

Article abstract of DOI:10.1039/c5nj02123e

Hydroxyapatite nanoparticles (HAP NPs) are found to be an efficient catalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media via a three-component one-pot condensation of isatoic anhydride and aromatic aldehydes with primary amines or ammonium salts. The nanocatalyst (characterized by FT-IR, XRD, SEM-EDS and TEM techniques) is easily recyclable six times without the significant loss of catalytic activity. Other remarkable features include the wide range of functional group tolerance and good to excellent yields of the products under mild reaction conditions.

Full text of DOI:10.1039/c5nj02123e

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Hydroxypatite nanoparticles (HAP NPs): As a green and efficient
heterogeneous catalyst for three-component one-pot synthesis of 2,3-
dihydroquinazolin-4(1H)-one derivatives in aqueous media
Nasrin Razavi, Batool Akhlaghinia*
Abstract
Hydroxypatite nanoparticles (HAP NPs) is found to be an efficient catalyst for synthesis of 2,3ꢀ
dihydroquinazolinꢀ4(1H)ꢀone derivatives in aqueous media via a threeꢀcomponent oneꢀpot
condensation of isatoic anhydride and aromatic aldehydes with primary amines or ammonium
salts. The nano catalyst (which characterized by FTꢀIR, XRD, SEMꢀEDS and TEM techniques)
is easily recyclable six times without the significant loss of catalytic activity. Other remarkable
features include the wide range of functional group tolerance and providing good to excellent
yields of the products under mild reaction conditions.
Keywords:
Hydroxypatite nanoparticles (HAP NPs), 2,3ꢀdihydroquinazolinꢀ4(1H)ꢀones, oneꢀpot reaction,
threeꢀcomponent reaction, heterogeneous catalyst.
Introduction
Quinazolinones derivatives as an important class of fused heterocyclic compounds and valuable
intermediates in synthetic organic chemistry are present in a large family of products with
potential biological and pharmaceutical activities.1 These exhibit various medicinal properties
such as antiꢀtumor,2 antiꢀcancer,3 antibacterial,4 anticonvulsant,5 antiꢀinflammatory,6 antifungal,7
antihypertension,8 antiꢀdiabetes,9 analgesic,10 herbicidal, diuretic, as well as plant growth

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regulation11 and some of them have been shown to act as potent HIVꢀ1 reverse transcriptase
inhibitors.12 In view of their widely increased application value, a number of classical methods
for the synthesis of 2,3ꢀdihydroquinazolinꢀ4(1H)ꢀones have been reported in the literature.13ꢀ15
These methods include: (i) condensation of oꢀaminobenzamide with aldehydes or ketones using
Lewis or Brønsted acids16 (ii) reductive cyclization of oꢀnitrobenzamide /or oꢀazidoꢀbenzamide
16 a,
with aldehydes or ketones using SnCl2/or metallic samarium in the presence of iodine or SmI2
17
(iii) condensation of isatoic anhydride, primary amine or ammonium salts with aldehydes or
ketones in the presence of pꢀtoluenesulfonic acid (PTSA),16 b citric acid,18 silica sulfuric acid
(SSA),19 silicaꢀbonded Nꢀpropylsulfamic acid,20 silicaꢀbonded Sꢀsulfonic acid,21 MCMꢀ41ꢀ
g
SO3H,22 ethylenediamine diacetate,16
Ga(OTf)3,23 KAl(SO4)2.12H2O,24 Al(H2PO4)3,25
montmorillonite Kꢀ10,26 heteropolyacids (HPAs),27 powdered diethylaminoethyl cellulose as
biomassꢀderived support for phosphotungstic acid,28 SrCl3.6H2O,29 molecular iodine,30 magnetic
Fe3O4, nanoꢀindium oxide, Al/Al2O3 nanoparticles,31ꢀ33 or with the aid of ultrasound irradiation
catalyzed by dodecylbenzenesulfonic acid34 and microwave in the presence of Amberlystꢀ1535 or
CuꢀCNTs.36
2,3ꢀDihydroquinazolinꢀ4(1H)ꢀone derivatives were previously prepared by multiꢀstep
reactions.37 In comparison multiꢀcomponent reactions (MCRs), not only produced 2,3ꢀ
dihydroquinazolinꢀ4(1H)ꢀone derivatives in a single step but also the diversity could be achieved
simply by varying the reacting components. Moreover, today development of an efficient, rapid,
simple, low cost, easy workꢀup and environmentally benign protocol with energy conservation
using a recyclable catalyst and a green solvent under mild reaction conditions for the synthesis
of 2,3ꢀdihydroquinazolinꢀ4(1H)ꢀone derivatives is desirable and in demand.38

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In recent years, HAP has attracted considerable interest in many areas. HAP as the main
component of hard tissues of vertebrates such as bones and teeth has properties such as ionꢀ
exchange ability, adsorption capacity, acidꢀbase properties and efficient catalytic activity in
organic reactions. The small size of HAP NPs as one of the important biocompatible and
bioactive material with higher surface area and lower particle size can provide greater catalytic
activity in organic synthesis. However, few common applications as catalyst or catalyst support
have emerged so far.39
In the present study, we would like to report a new application of HAP NPs, as an inexpensive,
nonꢀtoxic, nonꢀinflammatory, green heterogeneous catalyst for threeꢀcomponent oneꢀpot
synthesis of 2,3ꢀdihydroquinazolinꢀ4(1H)ꢀones in aqueous media.
Results and Discussion
Synthesis and characterization of HAP NPs
Following our interest in development of efficient and environmentally benign heterogeneous
catalysts in organic transformation,40 in this research, initially, HAP NPs was simply synthesized
according to the method reported previously (Scheme 1).41
Scheme 1 Preparation of HAP NPs.

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The nano catalyst was characterized by the following techniques: FTꢀIR spectroscopy, Xꢀray
diffraction (XRD), scanning electron microscopy (SEMꢀEDS) and transmission electron
microscopy (TEM).
The FTꢀIR spectrum of HAP NPs is shown in Figure 1. Broad bands centered at 3421 and 1649
cmꢀ1 are due to stretching and bending vibrations of molecularly adsorbed water. Also, the
stretching vibration around 3570 cmꢀ1 confirms the presence of hydroxyl groups. The absorption
bands at 1093 (νs, as), 1036 (νs, as), 604 (δ) and 567 (δ) cm−1 are attributed to asymmetric
stretching and bending vibration frequencies of PO43− ion respectively. The symmetric stretching
vibrations of the PO43− ion were also found at around 962 and 470 cm−1. The above results of FTꢀ
IR spectrum suggest that the HAP NPs were synthesized successfully.
120
100
80
1649
470
60
40
20
0
3421
3570
567
604
1036
1093
1400
3400
2400
400
Wavenumbers (cm -1)
Figure 1 FTꢀIR spectrum of HAP NPs.
Figure 2a shows the XRD pattern of HAP NPs. In pattern, well defined Bragg peaks were
obtained at specific 2 angles indicated that nanoparticles were ordered. The diffraction peaks,
θ
particularly in the planes (002), (211), (300), (202), (310), (222), (213) and (004) are wellꢀ
matched to hexagonal phase hydroxyapatite with space group of P63/m (JCPDS: 74ꢀ0565). The

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average crystallite size of HAP NPs were calculated to be 16 nm using the DebyeꢀScherrer
).42
equation d=K L/βcos(
θ
The structure and morphology of the HAP NPs were further confirmed by scanning electron
microscopy (SEM) (Figure 2b). It can be seen that the morphology of the synthesized HAP NPs
are nearly nanorod particles. As the shape of the synthesized HAP NPs is not clearly defined in
the SEM images (Figure 2b), the transmission electron microscopy (TEM) was recorded to
determine the exact size and shape of HAP NPs (Figure 2c). The TEM analysis revealed the
synthesized HAP NPs with nanorod shape and particle size of around 10 to 80 nm.
The energy dispersive spectrum (EDS) confirms the presence of Ca, P and O elements in the
structure of HAP NPs (Figure 2d).
a
b

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c
d
Figure 2 (a) XRD pattern of HAP NPs, (b) SEM images of HAP NPs, (c) TEM images of HAP
NPs, (d) The EDS spectrum of HAP NPs.
Synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives in the presence of HAP NPs
As a result of our great interest in preparation of heterocyclic compounds by applying
heterogeneous catalysts,40 a, b herein we wish to report an efficient procedure to synthesize 2,3ꢀ
dihydroquinazolinꢀ4(1H)ꢀone derivatives through a threeꢀcomponent oneꢀpot condensation of
isatoic anhydride, aromatic aldehyde and primary amines/ or ammonium salts using HAP NPs as
catalyst in aqueous media (Scheme 2).
O
CHO
O
R2(H)
R2NH2
or
(NH4 )+ Xꢀ
N
O
HAP NPs
H2O, 110 oC
+
+
N
H
R1
N
H
O
R1= H, 4ꢀOH, 2ꢀOH, 4ꢀOMe, 3ꢀOMe, 4ꢀMe,4ꢀN(Me)2, 4ꢀCl, 2,6(Cl)2, 4ꢀBr, 4ꢀCN
R2= Ph, 4ꢀMeC6H4, 4ꢀClC6H4, 4ꢀBrC6H4
R1
2ꢀ
X= AcOꢀ, Clꢀ, CO3

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Scheme 2 Synthesis of 2,3ꢀdisubstitutedꢀ2,3ꢀdihydroquinazolinꢀ4(1H)ꢀone derivatives in the
presence of HAP NPs in H2O.
Then, the reaction of isatoic anhydride, benzaldehyde and aniline was chosen a model reaction.
Subsequently, to study the effects of solvent, temperature, molar ratios of reactants and the
amount of catalyst on the reaction rate and yield, the model reaction was carried out under
different conditions. The results are summarized in Table 1. By applying 1:1:1 molar ratio of
isatoic anhydride: aniline: benzaldehyde in the absence of catalyst, the yield was poor even for
longer time (Table 1, entry 1). Among all the solvents screened, such as EtOH, H2O/EtOH (1:1),
acetonitrile, DMF, 1,4ꢀdioxane, EtOAc, dichloromethane and H2O, water is the best (Table
1,entries 2ꢀ9). The reaction temperature also played an important role in this reaction. Therefore,
we tried to optimize the reaction temperature on model reaction. As could be seen on Table 1, at
110ºC, the reaction proceeded quickly in highest yield (Table 1, entries 10, 11). It should be
noted that 0.05 g of catalyst was efficient enough to catalyze the reaction, and increasing the
amount of catalyst did not improve the yield significantly (Table 1, entry 12). The catalytic effect
of HAP NPs was efficiently decreased in solvent free condition (Table 1, entry 14). Additional
amounts of aniline or benzaldehyde has not any influence on the reaction rate (Table 1, entries
15ꢀ16).
Table 1 Synthesis of 2,3ꢀdiphenylꢀ2,3ꢀdihydroquinazolinꢀ4(1H)ꢀone in the presence of HAP NPs
under different reaction conditions.
Molar ratios of
Entry
1
isatoic anhydride:
aniline: benzaldehyde
Catalyst
(g)
Solvent
H2O
Temperature
(ºC)
Time
(h)
Isolated Yield
(%)
1:1:1
ꢀ
110
24
20

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2
3
4
5
6
7
8
9
1:1:1
1:1:1
1:1:1
1:1:1
1:1:1
1:1:1
1:1:1
1:1:1
0.05
0.05
0.05
0.05
0.05
0.05
0.05
0.05
EtOH
80
80
3
3
5
6
6
5
6
3
85
80
40
50
20
60
10
85
H2O/ EtOH
(1:1)
CH3CN
80
DMF
120
101
77
1,4
Dioxane
EtOAc
CH2Cl2
H2O
40
100
10
11
12
13
1:1:1
1:1:1
1:1:1
1:1:1
0.05
0.05
0.1
H2O
H2O
H2O
H2O
110
120
110
110
1
1
1
4
95
95
95
80
0.025
14
15
1:1:1
0.05
0.05
ꢀ
110
110
6
1
60
95
1:1.2:1
H2O
16
1:1:1.2
0.05
H2O
110
1
95
Encouraged by the initial success in the production of 2,3ꢀdiphenylꢀ2,3ꢀdihydroquinazolinꢀ
4(1H)ꢀone via the multicomponent reaction strategy, to investigate the general scope and
versatility of this method in the preparation of substituted 2,3ꢀdihydroquinazolinꢀ4(1H)ꢀone
derivatives, isatoic anhydrides, different substituted amines and aldehydes were examined under
optimized conditions. Condensation of aniline with commercially available aromatic aldehydes
having electronꢀdonating and electron withdrawing substituents produced 3aꢀl in high yields
(Table 2, entries 1ꢀ12). According to the results, aldehydes bearing electronꢀdonating groups

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produced the desired products more quickly than the aldehydes with electronꢀwithdrawing
groups. Though metaꢀ and para substituted aromatic aldehydes reacted quickly, orthoꢀsubstituted
aromatic aldehydes give product in longer reaction time (Table 2, entry 9, 10). Subsequently, the
substrate scope of amines was examined for this threeꢀcomponent reaction. From Table 2, it can
be observed that in the condensation reaction of substituted anilines with aromatic aldehydes the
nature of substituent on the aromatic ring of amines has no noticeable effect on the reaction rate
as the corresponding products were obtained in high yields and in short reaction times (Table 2,
entries 13ꢀ15). Excitingly, the results shown in Table 2 confirm that the reaction was compatible
successfully with a broad range of substituents (both electronꢀdonating and electronꢀwithdrawing
groups) in the amines or the aldehydes.
Table 2 Synthesis of 2,3ꢀdihydroquinazolinꢀ4(1H)ꢀones catalyzed by HAP NPs.
Entry
R1
R2
Product
Time(min)
Isolated Yield (%)
1
2
3
4
H
H
H
H
H
3a
3b
3c
3d
60
30
30
30
95
90
90
95
4ꢀOH
2ꢀOH
4ꢀOMe

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5
6
H
H
3ꢀOMe
3e
3f
30
30
30
60
180
60
60
60
30
90
95
4ꢀMe
7
H
N(Me)2
4ꢀCl
3g
3h
87
85
8
H
9
H
2,6ꢀ(Cl)2
5ꢀBrꢀ2ꢀOH
4ꢀBr
3i
3j
85
90
90
90
85
10
11
12
13
H
H
3k
3l
4ꢀCN
H
H
4ꢀMe
3m
H
H
14
15
16
17
18
4ꢀCl
4ꢀBr
4ꢀMe
4ꢀMe
4ꢀBr
3n
3o
3p
3q
3r
30
30
40
45
60
90
90
80
75
85
4ꢀMe
4ꢀOMe
4ꢀMe
As some ammonium salts are the source of ammonia in the synthesis of nitrogen containing
heterocyclic compounds, 2,3ꢀdihydroquinazolinꢀ4(1H)ꢀones derivatives were prepared under the
optimal reaction conditions with different ammonium sources such as acetate, chloride and
carbonate (Table 3). Accordingly, the corresponding 2,3ꢀdihydroquinazolinꢀ4(1H)ꢀones (4aꢀc)
were synthesized efficiently in the presence of HAP NPs. In comparison, under the same reaction
conditions ammonium acetate was reacted more quickly with isatoic anhydride and aldehyde
than ammonium chloride and ammonium carbonate.

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Table 3 Synthesis of 2,3ꢀdihydroquinazolinꢀ4(1H)ꢀones derivatives using ammonium salts in the
presence of HAP NPs.
Entry
Ammonium
salts
R1
Product
Time (min)
Isolated Yield (%)
1
2
3
4
5
6
NH4OAc
NH4Cl
H
H
4a
4a
4a
4b
4c
4c
60
90
90
85
80
90
85
80
(NH4)2CO3
NH4OAc
NH4OAc
NH4Cl
H
90
4ꢀMe
4ꢀCl
4ꢀCl
45
60
120
1
13
All known products were characterized by comparing their physical data and H and C NMR
spectra with those of authentic samples reported in the literature. Also, most of the known
products were characterized by FTꢀIR spectroscopy, mass spectrometry and elemental analysis.
The data for novel compounds (Table 2, 3j and 3r) are reported in this paper.
In the FTꢀIR spectra of compounds 3aꢀr, the strong and sharp absorption bands due to NH and
C=O groups were observed around 3379ꢀ 3282 cm−1 and 1655ꢀ1608 cm−1 respectively.
Moreover, absorption bands at 3312ꢀ3303 and 3192ꢀ3187 cmꢀ1 in the FTꢀIR spectra of
compounds 4aꢀc can be attributed to stretching vibrations of NH and NHꢀCO respectively. Also,
1
in the HNMR spectra, the NH proton of dihydroquinazolin ring, appeared as a broad signal at

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13
8.36ꢀ7.03 ppm. C NMR spectra show a signal at 171ꢀ162 ppm which assigned to C=O group
that confirmed the synthesis of 2,3ꢀdihydroquinazolinꢀ4(1H)ꢀones.
31, 32
On the basis of our experimental results and by referring to the literature,23,
the plausible following mechanism was proposed to account the condensation of isatoic
anhydride and aromatic aldehydes with primary amines/ or ammonium salts catalysed by HAP
NPs (Scheme 3). The question is how this catalyst operates? Evidently, HAP NPs function as a
good Lewis acid, which in the initial step attracts and activates the isatoic anhydride (1) by
coordination with carbonyl groups and provides active sites on which the reaction occurs
successively leading to the desired product. The nucleophilic attack of primary amine/ or
ammonium salt (2) to carbonyl group followed by extrusion of CO2 results the formation of
intermediate I. HAP NPs also promote the condensation of I with aldehyde (3) which produces
an imine intermediate III. An intramolecular nucleophilic attack of the amide nitrogen to imine,
which is catalysed by HAP NPs, produces cyclized intermediate V which upon 1,5ꢀproton
transfer leads to formation of 2,3ꢀdihydroquinazolinꢀ4(1H)ꢀones. Finally, HAP NPs reꢀenter to
the catalytic cycle. Nevertheless, at this time there is no experimental evidence for the formation
of the above mentioned intermediates in this manner, and further studies to elucidate the details
of the mechanism are ongoing.

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Scheme 3 Plausible reaction pathway catalysed by HAP NPs.

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To investigate the reusability of HAP NPs, after initial experimentation, the catalyst was
recovered by centrifugation, washed with hot ethanol, dried under vacuum at 50 ºC and subjected
to second run (Figure 3). The results of this experiment and five subsequent experiments were
almost consistent in yields (95, 95, 95, 92, 90, 90 %). Although slightly more time was required
to complete the reaction in the sixth run, the yields are comparable to those seen earlier.
98
98
98
98
96
94
92
90
88
86
95
95
95
95
95
95
92
90
90
First
Second
Third
Fourth
Fifth
Sixth
Isolated Yield (%)
Conversion*
* The data referred to conversion of benzaldehyde.
Figure 3 Synthesis 2,3ꢀdiphenylꢀ2,3ꢀdihydroquinazolinꢀ4(1H)ꢀone in the presence of reused
HAP NPs.
Finally, the efficiency of the present protocol was compared with different heterogeneous
catalysts reported previously in literature. The results are shown in Table 4. It can be seen from
Table 4, that the green nano catalyst gives better yield in shorter reaction time than the other
heterogeneous catalysts.

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Table 4 Comparison of catalytic activity between HAP NPs and other reported catalysts.
Entry
Catalyst
Solvent
Temperature
(°C)
Time Yield
Reference
(min)
(%)
1
2
3
Ga(OTf)3
EtOH
H2O
70
reflux
80
60
79
23
24
32
KAl(SO4)2.12H2O
Nanoꢀindium oxide
60
65
EtOH/H2O
(1/2)
320
87
4*
5
PTA@DEAEC
Silica sulfuric acid
Nano Fe3O4
EtOH
EtOH
H2O
reflux
reflux
reflux
360
390
120
79
80
80
28
19
31
6
7
8
SrCl3.6H2O
EtOH/H2O
(1/3 )
reflux
110
90
60
94
95
29
Hydroxypatite
H2O
present study
nanoparticles (HAP)
*
Powdered diethylaminoethyl cellulose as biomassꢀderived support for phosphotungstic acid.
Conclusion
In summary, we have described for the first time, a successful strategy for the
efficient and convenient preparation of substituted 2,3ꢀdihydroquinazolinꢀ4(1H)ꢀone derivatives
using HAP NPs as a catalyst in water by the multiꢀcomponent oneꢀpot condensation of isatoic
anhydride with amines/ or ammonium salts and aldehydes. The novelty and synthetic valuability
of this methodology developed the mild reaction conditions, avoiding the use of organic
solvents, easy experimental procedure, ease of product isolation, and recovery of the catalyst for
at least six runs without any significant impact on the yield of the products. These conditions
may be ideally suited for an effective synthesis on a larger scale.
Experimental
General

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The purity determinations of the products were accomplished by thin layer chromatography
(preparative TLC was carried out using a Merck GF 254 silica gel on a glass support). The
melting points of products were determined with an Electrothermal Type 9100 melting point
apparatus. The FTꢀIR spectra were recorded on an Avatar 370 FTꢀIR Therma Nicolet
spectrometer. The NMR spectra were provided on Brucker Avance 300, 400 and 500 MHz
instruments in DMSOꢀd6 and CDCl3. Elemental analyses were performed using a Thermo
Finnegan Flash EA 1112 Series instrument. Mass spectra were recorded with a CH7A Varianmat
Bremem instrument at 70 eV; in m/z (rel %). Transmission electron microscopy (TEM) was
performed with a Leo 912 AB (120 kV) microscope (Zeiss, Germany). Elemental compositions
were determined with a Leo 1450 VP scanning electron microscope equipped with an SC7620
energy dispersive spectrometer (SEMꢀEDS) presenting a 133 eV resolution at 20 kV. The crystal
structure of catalyst was analyzed by Xꢀray diffraction (XRD) with a Bruker D8 ADVANCE
diffractometer using a Cu target (λ= 1.54 Å). All yields refer to isolated products after
purification by recrystallization or thin layer chromatography.
Preparation of HAP NPs
To a solution of Ca(NO3)2 .4 H2O (50 mL, 1.08 M , at pH adjusted to 10 with NH4OH ) in a
threeꢀnecked 500 mL roundꢀbottomed flask equipped with condenser, argon gas inlet tube and
dropping funnel, solution of (NH4)2HPO4 (50 mL , 0.65 M at pH adjusted to 10 with NH4OH)
was added at 90 °C with stirring. After 5h the suspension was centrifuged at 10,000 rpm for 10
min and washed repeatedly with CO2ꢀfree distilled water (3×20 mL). HAP NPs were dried at
50°C under vacuum for 12h.41
Typical procedure for synthesis of 2,3-diphenyl-2,3-dihydroquinazolin-4(1H)-one

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HAP NPs (0.05 g) was added to a mixture of isatoic anhydride (1 mmol, 0.163 g), benzaldehyde
(1 mmol, 0.106 g) and aniline (1 mmol, 0.093 g) in H2O (5 mL). The mixture was stirred for 1h
º
at 110 C. The progress of reaction was monitored by TLC (EtOAc: petroleum ether, 1:2). After
completion of the reaction, the nano catalyst was separated by centrifugation. The mixture was
extracted by ethyl acetate (3×3 mL). The organic layer was dried over anhydrous sodium sulfate.
Ethyl acetate was evaporated under reduced pressure to give the crude product. Pure product was
obtained by recrystallization from ethanol obtaining 0.285 g of white solid (95% yield).
2,3-Diphenylquinazolin-4(1H)-one (3a):31 white solid; mp 205ꢀ206 ºC; FTꢀIR (KBr): νmax/cmꢀ1
3294 (NH), 3064, 3031, 2917, 2827, 2761, 1634 (CO), 1613, 1510, 1488, 1454, 1390, 1358,
1311, 1248, 1159, 1025, 923, 868, 808, 751, 695, 620, 542, 506; 1H NMR (300 MHz, DMSOꢀd6,
ppm) δ 6.27 (s, 1H, CH), 6.77ꢀ6.70 (m, 2H, Ph), 7.50ꢀ7.08 (m, 8H, Ph), 7.73ꢀ7.69 (m, 3H), 7.90
(d, J= 11.7 Hz, 2H, Ph); 13C NMR (75 MHz, DMSOꢀd6, ppm) δ 73.7, 115.6, 115.7, 123.9, 125.9,
126.4, 126.6, 127.0, 128.5, 128.7, 129.3, 130.1, 134.1, 137.3, 141.1, 146.0, 168.4; MS, m/z (%):
300 [3, M+], 195 [32, M+ꢀ105], 119 [42, M+ꢀ181].
2-(4-Hydroxyphenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one (3b):43 white solid; mp 228ꢀ
229 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3330 (NH), 3210, 3056, 3031, 2835, 2810, 1608 (CO), 1568,
1
1501, 1453, 1413, 1272, 1222, 1167, 1153, 1115, 874, 835, 757, 697, 608, 531, 489; H NMR
(300 MHz, DMSOꢀd6, ppm) δ 6.16 (s, 1H, CH), 6.64ꢀ6.77 (m, 4H, Ph), 7.16ꢀ7.34 (m, 8H, Ph),
7.50 (1H, br s, NH), 7.72 (dd, J= 7.5 Hz, J= 1.2 Hz, 1H, Ph), 9.49 (1H, br s, OH); 13C NMR (100
MHz, DMSOꢀd6, ppm) δ 72.5, 114.6, 114.9, 115.2, 117.2, 125.9, 126.5, 127.8, 127.9, 128.4,
130.8, 133.6, 140.8, 146.7, 157.3, 162.3; MS, m/z (%):316 [40, M+], 223 [84, M+ꢀ93].
2-(2-Hydroxyphenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one (3c):43 white solid; mp 199ꢀ
201 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3294 (NH), 3231, 3068, 2925, 2839, 1613 (CO), 1487, 1396,

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1
1352, 1296, 1233, 1158, 1109, 1029, 845, 790, 751, 696, 629, 551, 527; H NMR (400 MHz,
DMSOꢀd6, ppm) δ 6.39 (s, 1H, CH), 6.71 (t, J= 7.4 Hz, 2H, Ph), 6.81 (dd, J= 11.2 Hz, J= 8.8 Hz,
2H, Ph), 7.09 (t, J= 7.6 Hz, 1H, Ph), 7.17 (d, J= 13.3 Hz, 2H, Ph), 7.30ꢀ7.20 (m, 4H, Ph), 7.33 (t,
J= 7.5 Hz, 2H, Ph), 7.76 (d, J= 7.6 Hz, 1H, NH), 10.01 (s, 1H, OH); 13C NMR (100 MHz,
DMSOꢀd6, ppm) δ 68.1, 114.9, 114.9, 115.5, 117.3, 118.6, 126.0, 126.1, 126.6, 127.8, 128.5,
129.3, 133.5, 140.8, 146.6, 154.1, 162.5; MS, m/z (%):316 [2.5, M+], 223 [100, M+ꢀ93], 119 [32,
M+ꢀ197].
2-(4-Methoxyphenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one (3d):43 white solid; mp 201ꢀ
203 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3297 (NH), 3064, 3015, 2933, 2839, 1634 (CO), 1611, 1589,
1
1509, 1488, 1390, 1300, 1250, 1170, 1111, 1029, 874, 835, 750, 695, 604, 552; H NMR (300
MHz, DMSOꢀd6, ppm) δ 3.68 (s, 3H, OCH3), 6.21 (s, 1H, CH), 6.86ꢀ6.77 (m, 2H, Ph), 7.35ꢀ7.09
13
(m, 5H, Ph), 7.49ꢀ7.44 (m, 3H, Ph), 7.90ꢀ7.69 (m, 4H); C NMR (75 MHz, DMSOꢀd6, ppm) δ
55.4, 72.9, 114.1, 115.0, 115.4, 115.6, 117.8, 127.0, 127.2, 128.3, 128.8, 133.9, 134.0, 141.2,
147.2, 156.6, 163.2; MS, m/z (%):330 [7, M+], 236 [100, M+ꢀ93], 120 [33, M+ꢀ210].
2-(3-Methoxyphenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one (3e):44 white solid; mp 187ꢀ
189 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3290 (NH), 3011, 2933, 2843, 1637 (CO), 1610, 1503, 1489,
1395, 1319, 1263, 1172, 1155, 1033, 874, 799, 771, 760, 701, 534; 1H NMR (300 MHz, DMSOꢀ
d6, ppm) δ 3.68 (3H, OCH3), 6.25 (s, 1H, CH), 6.70ꢀ6.85 (m, 3H, Ph), 6.94ꢀ6.95 (m, 2H, Ph),
13
7.18ꢀ7.38 (m, 7H, Ph), 7.65 (1H, br s, NH), 7.72 (dd, J= 7.8 Hz, J= 1.2 Hz, 1H, Ph); C NMR
(100 MHz, CDCl3, ppm) δ 54.4, 73.1, 112.9, 113.7, 115.8, 118.5, 125.7, 126.0, 127.1, 127.8,
128.0, 130.7, 132.7, 139.3, 144.4, 158.9, 162.3; MS, m/z (%):330 [5, M+], 236 [100, M+ꢀ93], 119
[46, M+ꢀ211].

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2-(4-Methylphenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one (3f):31 white solid; mp 214ꢀ
215; FTꢀIR (KBr): νmax/cmꢀ1 3298 (NH), 3060, 2921, 2823, 1635 (CO), 1612, 1507, 1489, 1393,
1
1311, 1249, 1159, 1111, 1025, 874, 820, 750, 695, 604, 547, 481; H NMR (300 MHz, DMSOꢀ
d6, ppm) δ 2.25 (s, 3H, CH3), 6.16 (d, J= 2.7 Hz, 1H, CH), 6.86ꢀ6.70 (m, 4H, Ph), 7.29ꢀ7.11 (m,
8H, Ph), 7.51 (1H, br s, NH), 7.70 (d, J= 11.4 Hz, 1H, Ph); 13C NMR (75 MHz, DMSOꢀd6, ppm)
δ 20.6, 75.8, 110.1, 115.2, 122.5, 123.4, 123.7, 125.3, 127.5, 128.0, 128.8, 129.6, 132.4, 136.8,
137.7, 141.3, 144.1, 146.9, 171.5; MS, m/z (%): 314 [46, M+], 221 [100, M+ꢀ93], 119 [65, M+ꢀ
195].
2-(4-(Dimethylamino)phenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one (3g):45 white solid;
mp 183ꢀ184 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3297 (NH), 3056, 2990, 2888, 2802, 1634 (CO), 1611,
1
1523, 1504, 1441, 1394, 1347, 1188, 1160, 1049, 947, 878, 823, 756, 694, 604, 549; H NMR
(300 MHz, DMSOꢀd6, ppm) δ 2.83 (s, 6H, CH3), 6.13 (s, 1H, CH), 6.60ꢀ6.63 (m, 2H, Ph), 6.68ꢀ
6.76 (m, 2H, Ph), 7.16ꢀ7.35 (m, 8H, Ph), 7.72 (dd, J= 7.8 Hz, J= 1.2 Hz, 1 H, Ph); 13C NMR (75
MHz, DMSOꢀd6, ppm) δ 72.9, 73.0, 112.2, 115.1, 115.8, 117.7, 126.3, 126.6, 127.8, 128.2,
128.3, 129.0, 134.0, 141.4, 147.1, 147.2, 150.6, 162.8; MS, m/z (%): 343 [3, M+], 221 [74, M+ꢀ
122], 119 [67, M+ꢀ224].
2-(4-Chlorophenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one (3h):34 white solid; mp 219ꢀ
220 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3296 (NH), 3064, 2937, 2814, 2753, 1633 (CO), 1613, 1508,
1
1488, 1414, 1390, 1312, 1249, 1159, 1088, 1014, 869, 832, 754, 694, 587, 543, 516; H NMR
(300 MHz, DMSOꢀd6, ppm) δ 6.33 (s, 1H, CH), 6.72ꢀ6.80 (m, 2H, Ph), 7.18ꢀ7.43 (m, 10H, Ph),
13
7.67 (1H, br s, NH), 7.72 (dd, J= 7.8 Hz, J= 1.2 Hz, 1H, Ph); C NMR (75 MHz, DMSOꢀd6,
ppm) δ 73.6, 114.2, 115.0, 115.5, 115.6, 117.8, 127.0, 127.2, 128.6, 128.8, 133.8, 134.0, 141.2,
147.1, 162.8; MS, m/z (%): 336 [3, M++2], 334 [28, M+], 241 [86, M+ꢀ93], 222 [75, M+ꢀ112].

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2-(2,6-Dichlorophenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one (3i):46 white solid; mp
234ꢀ236 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3282 (NH), 3064, 1630 (CO), 1533, 1490, 1439, 1414,
1342, 1315, 1249, 1194, 1127, 865, 784, 749, 697, 518; 1H NMR (300 MHz, DMSOꢀd6, ppm) δ
6.65 (d, J= 8.1 Hz, 1H, Ph), 6.69 (s, 1H, CH), 7.14ꢀ7.41 (m, 10H, Ph), 7.67 (dd, J= 7.8 Hz, J=
1.2 Hz, 1H, Ph); 13C NMR (75 MHz, DMSOꢀd6+CDCl3, ppm) δ 69.2, 114.1, 114.4, 117.5, 125.4,
125.8, 126.4, 127.3, 127.9, 128.1, 128.6, 131.6, 132.9, 133.8, 135.0, 139.3, 144.6, 161.9; MS,
m/z (%): 371 [30, M++2], 369 [85, M+], 222 [100, M+ꢀ147], 120 [40, M+ꢀ249].
2-(5-Bromo-2-hydroxyphenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one (3j): white solid;
mp 208ꢀ210 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3379 (NH), 3141, 2937, 2708, 2573, 1632 (CO), 1609,
1
1491, 1441, 1405, 1322, 1271, 1247, 1227, 1110, 1077, 922, 856, 816, 762, 702, 619, 525; H
NMR (300 MHz, DMSOꢀd6, ppm) δ 6.38 (s, 1H, CH), 6.83ꢀ6.72 (m, 3H, Ph), 7.38ꢀ7.19 (m, 8H,
Ph), 7.77 (dd, J= 7.8 Hz, J= 1.2 Hz, 1H, Ph), 10.37 (1H, br s, OH); 13C NMR (75 MHz, DMSOꢀ
d6, ppm) δ 68.2, 68.3, 110.3, 115.2, 115.3, 118.1, 118.2, 126.5, 126.7, 128.3, 129.0, 129.2, 129.7,
132.6, 134.3, 141.0, 146.9, 154.0, 154.2, 162.9; MS, m/z (%): 397 [5, M++2], 395 [41, M+], 222
[64, M+ꢀ1173], 120 [44, M+ꢀ275]; Anal. Calcd for C20H15Br N2O2. Calcd. C, 60.78; H, 3.83; N,
7.09; O, 8.10. Found, C, 60.56; H, 3.58; N, 6.85; O, 7.9 %.
2-(4-Bromophenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one (3k):31 white solid; mp 222ꢀ
223 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3295 (NH), 3058, 3031, 2941, 2831, 2745, 1634 (CO), 1609,
1585, 1486, 1412, 1388, 1312, 1248, 1158, 1113, 1070, 1009, 910, 871, 827, 752, 694, 623, 542,
513; 1H NMR (300 MHz, DMSOꢀd6, ppm) δ 6.30 (d, J= 3.6 Hz, 1H, CH), 6.78ꢀ6.69 (m, 2H, Ph),
7.38ꢀ7.16 (m, 8H, Ph), 7.53ꢀ7.49 (m, 2H, Ph), 7.74ꢀ7.65 (m, 2H), 13C NMR (75 MHz, DMSOꢀd6,
ppm) δ 72.4, 115.3, 115.7, 118.1, 121.1, 121.9, 126.6, 128.4, 129.1, 129.2, 131.7, 134.2, 140.5,

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141.0, 146.8, 162.5; MS, m/z (%): 381 [5, M++2], 379 [95, M+], 286 [96, M+ꢀ93], 222 [95, M+ꢀ
157].
2-(4-Cyanophenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one (3l):31 white solid; mp 203ꢀ
204 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3310 (NH), 3051, 2937, 2228 (CN), 1641 (CO), 1617, 1490,
1
1443, 1395, 1323, 1238, 1188, 1151, 1082, 914, 820, 761, 746, 697, 582, 530; H NMR (400
MHz, CDCl3, ppm) δ 5.045 (s, 1H, NH), 6.12 (s, 1H, CH), 6.66 (d, J= 8 Hz, 1H, CH), 6.93ꢀ6.85
(m, 1H, Ph), 7.34ꢀ7.06 (m, 6H, Ph), 7.47 (d, J= 8 Hz, 2H, Ph), 7.55 (d, J= 8 Hz, 2H, Ph), 7.99 (d,
J= 7.6 Hz, 1H, Ph); 13C NMR (125 MHz, CDCl3, ppm) δ 73.7, 112.8, 115.3, 117.1, 118.1, 120.2,
126.5, 127.1, 127.5, 129.1, 129.2, 132.5, 134.2, 140.2, 144.6, 145.0, 162.7; MS, m/z (%): 325 [2,
M+], 221 [87, M+ꢀ104], 119 [ 66, M+ꢀ206].
3-(4-Methylphenyl)-2-phenyl-2,3-dihydroquinazolin-4(1H)-one (3m):34 white solid; mp 198ꢀ
199 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3298 (NH), 3060, 3035, 2921, 2835, 1635 (CO), 1611, 1511,
1
1486, 1455, 1395, 1334, 1313, 1241, 1157, 1111, 1029, 878, 821, 753, 699, 604, 516; H NMR
(300 MHz, DMSOꢀd6, ppm) δ 2.26 (s, 3H, CH3), 6.24 (s, 1H, CH), 6.77ꢀ6.69 (m, 2H, Ph), 7.39ꢀ
13
7.11 (m, 10H, Ph), 7.72 (dd, J= 7.8 Hz, J= 1.5 Hz, 1H, Ph); C NMR (100 MHz, DMSOꢀd6,
ppm) δ 20.6, 72.8, 114.8, 115.4, 117.5, 126.2, 126.6, 128.0, 128.3, 128.4, 129.2, 133.8, 135.4,
138.3, 140.8, 146.6, 162.3.
3-(4-Chlorophenyl)-2-phenyl-2,3-dihydroquinazolin-4(1H)-one (3n):31 white solid; mp 216ꢀ
217 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3298 (NH), 3063, 3035, 2945, 2839, 2753, 1633 (CO), 1608,
1
1510, 1490, 1453, 1392, 1314, 1249, 1158, 1089, 1017, 869, 821, 754, 700, 630, 506, 438; H
NMR (500 MHz, DMSOꢀd6, ppm) δ 6.22 (d, J= 3.0 Hz, 1H, CH), 6.68ꢀ6.61 (m, 2H, Ph), 7.29ꢀ
7.16 (m, 10H, Ph), 7.57 (1H, br s, NH), 7.63 (d, J= 7.8 Hz, 1H, Ph); 13C NMR (125 MHz,
DMSOꢀd6, ppm) δ 72.9, 115.2, 115.4, 118.0, 122.1, 127.1, 128.4, 128.5, 128.7, 128.8, 128.9,

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130.5, 134.3, 139.9, 140.7, 147.1, 162.8; MS, m/z (%): 334 [5, M+], 254 [40, M+ꢀ80], 206 [98,
M+ꢀ128].
3-(4-Bromophenyl)-2-phenyl-2,3-dihydroquinazolin-4(1H)-one (3o):31 white solid; mp 228ꢀ
229 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3300 (NH), 3056, 3035, 2929, 2831, 1633 (CO), 1609, 1578,
1510, 1487, 1456, 1389, 1314, 1250, 1159, 1067, 1012, 872, 820, 789, 755, 701, 627, 562, 506;
1H NMR (300 MHz, DMSOꢀd6, ppm) δ 6.31 (d, J= 3.6 Hz, 1H, CH), 6.78ꢀ6.69 (m, 2H, Ph),
13
7.37ꢀ7.15 (m, 8H, Ph), 7.51ꢀ 7.50 (m, 2H, Ph), 7.74ꢀ7.64 (m, 2H); C NMR (75 MHz, DMSOꢀ
d6, ppm) δ 72.7, 115.3, 115.7, 118.1, 121.1, 121.9, 126.6, 128.4, 129.1, 129.2, 131.7, 134.3,
140.5, 141.0, 146.9, 162.6; MS, m/z (%): 379 [30, M+], 300 [77, M+ꢀ79], 206 [100, M+ꢀ173].
2,3-Di(4-methylphenyl)-2,3-dihydro-quinazolin-4(1H)-one (3p):47 white solid; mp 242ꢀ243
ºC; FTꢀIR (KBr): νmax/cmꢀ1 3297 (NH), 3060, 3039, 2962, 2933, 2835, 2757, 1637 (CO), 1609,
1510, 1484, 1439, 1391, 1300, 1245, 1157, 1107, 1028, 874, 820, 784, 753, 694, 602, 549, 515;
1H NMR (300 MHz, DMSOꢀd6, ppm) δ 2.26 (s, 3H, CH3), 3.69 (s, 3H, CH3), 6.17 (s, 1H, CH),
6.72ꢀ6.76 (m, 2H, Ph), 6.83 (d, J= 3 Hz, 1H, Ph), 6.87 (d, J= 2.7 Hz, 1H, Ph), 7.30ꢀ7.12 (m, 7H,
Ph), 7.71 (dd, J= 7.8 Hz, J= 1.2 Hz, 1H, Ph); 13C NMR (75 MHz, DMSOꢀd6, ppm) δ 21.0, 73.2,
115.1, 115.2, 115.8, 117.9, 126.6, 127.0, 128.6, 128.7, 128.8, 129.5, 134.1, 135.7, 138.7, 141.2,
146.9, 147.0, 162.7.
2-(4-Methoxyphenyl)-3-(p-tolyl)-2,3-dihydroquinazolin-4(1H)-one (3q):31 white solid; mp
247ꢀ249 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3297 (NH), 3060, 3032, 2964, 2836, 2761, 1637 (C=O),
1609, 1510, 1484, 1439, 1391, 1300, 1245, 1157, 1107, 1028, 882, 820, 784, 753, 695, 656, 602,
549, 515; 1H NMR (300 MHz, DMSOꢀd6, ppm) δ 2.25 (s, 3H, CH3), 3.68 (s, 3H, OCH3), 6.16 (d,
J= 2.7 Hz, 1H, CH), 6.86ꢀ6.70 (m, 4H, Ph), 7.29ꢀ7.11 (m, 7H, Ph), 7.50 (1H, br s, NH), 7.70 (d,
J= 11.4 Hz, 1H, Ph); 13C NMR (75 MHz, DMSOꢀd6, ppm) δ 20.6, 55.4, 72.4, 110.1, 115.3,

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122.5, 123.5, 123.7, 125.3, 127.5, 128.0, 128.8, 129.6, 132.5, 136.8, 137.6, 141.3, 144.2, 146.8,
158.7, 171.3; MS, m/z (%): 344 [3, M+], 236 [100, M+ꢀ108], 91 [45, M+ꢀ239].
3-(4-Bromophenyl)-2-(p-tolyl)-2,3-dihydroquinazolin-4(1H)-one (3r): white solid; mp 247ꢀ
249 ºC; FTꢀIR (KBr): νmax/cmꢀ1 3306 (NH), 3051, 2945, 2921, 2827, 1634 (CO), 1608, 1580,
1
1507, 1487, 1386, 1332, 1315, 1250, 1159, 1070, 1012, 874, 820, 752, 752, 489; H NMR (300
MHz, DMSOꢀd6, ppm) δ 2.23 (s, 3H, CH3), 6.26 (s, 1H, CH), 6.70ꢀ6.78 (m, 2H, Ph), 7.11 (d, J=
8.1 Hz, 2H, Ph), 7.21ꢀ7.31 (m, 5H, Ph), 7.51 (d, J= 8.4 Hz, 2H, Ph), 7.63 (1H, br s, NH), 7.72 (d,
J = 7 Hz, 1H, Ph); 13C NMR (75 MHz, DMSOꢀd6, ppm) δ 21.0, 72.6, 72.7, 115.2, 115.3, 115.5,
118.0, 118.9, 127.0, 128.4, 128.7, 129.4, 131.9, 134.3, 137.8, 138.2, 140.4, 147.0, 147.1, 162.8;
MS, m/z (%): 393 [87, M+];300 [70, M+ꢀ93], 220 [100, M+ꢀ173]; Anal. Calcd for C22H20N2O2.
Calcd. C, 76.72; H, 5.85; N, 8.13; O, 9.29. Found, C, 76.42; H, 5.53; N, 7.88; O, 9.03 %.
2-Phenyl-2,3-dihydroquinazolin-4(1H)-one (4a):30 white solid; mp 223ꢀ224 ºC; FTꢀIR (KBr):
νmax/cmꢀ1 3303 (NH), 3187 (NH), 3129, 3060, 3031, 2941, 2802, 2708, 1655 (CO), 1613, 1511,
1
1483, 1439, 1390, 1300, 1237, 1148, 1029, 914, 861, 810, 748, 699, 663, 641, 529, 489; H
NMR (400 MHz, DMSOꢀd6, ppm) δ 5.76 (s, 1H, CH), 6.67 (t, J= 7.6 Hz, 1H, Ph), 6.75 (d, J= 8.0
Hz, 1H, Ph), 7.12 (s, 1H, NH), 7.24 (t, J= 7.6 Hz, 1H, Ph), 7.41ꢀ7.34 (m, 3H, Ph), 7.50 (d, J=7.6
Hz, 2H, Ph), 7.61 (d, J= 7.6 Hz, 1H, Ph), 8.30 (s, 1H, NH); 13C NMR (100 MHz, DMSOꢀd6,
ppm) δ 66.5, 114.4, 114.9, 117.1, 126.9, 127.4, 128.3, 128.5, 133.3, 141.6, 147.9, 163.6; MS, m/z
(%): 224 [5, M+], 146 [100, M+ꢀ78], 119 [87, M+ꢀ105].
2-(p-Tolyl)-2,3-dihydroquinazolin-4(1H)-one (4b):30 white solid; mp 228ꢀ230 ºC; FTꢀIR
(KBr): νmax/cmꢀ1 3312 (NH), 3192 (NH), 3133, 3062, 2941, 2851, 1658 (CO), 1609, 1564, 1509,
1484, 1441, 1385, 1298, 1245, 1150, 1131, 1020, 943, 822, 771, 751, 685, 656, 611, 530, 503,
424; 1H NMR (300 MHz, DMSOꢀd6, ppm) δ 2.29 (s, 3H, CH3), 5.70 (s, 1H, CH), 6.75ꢀ6.66 (m,

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2H, Ph), 7.03 (1H, br s, NH), 7.38ꢀ7.16 (m, 5H, Ph), 7.60 (d, J= 10.2 Hz, 1H, Ph), 8.21 (1H, br s,
NH);13C NMR (75 MHz, DMSOꢀd6, ppm) δ 21.1, 66.8, 114.8, 115.4, 117.4, 127.2, 127.7, 129.2,
133.6, 138.1, 139.1, 148.3, 164.0; MS, m/z (%): 238 [3, M+], 146 [96, M+ꢀ92], 119 [100, M+ꢀ
119].
1
2-(4-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one (4c):30 white solid; mp 206ꢀ207 ºC; H
NMR (300 MHz, DMSOꢀd6, ppm) δ 5.78 (s, 1H, CH), 6.67ꢀ6.77 (m, 2H, Ph), 7.17 (1H, br s,
NH), 7.26 (t, J= 7.8 Hz, 1H, Ph), 7.41ꢀ7.61 (m, 4H, Ph), 7.64 (d, J= 5.5 Hz, 1H, Ph), 8.36 (1H, br
13
s, NH); C NMR (100 MHz, DMSOꢀd6, ppm) δ 65.8, 114.5, 114.9, 117.3, 127.4, 128.3, 128.8,
133.0, 133.4, 140.7, 147.7, 163.5; MS, m/z (%): 258 [22, M+], 146 [100, M+ꢀ112], 120 [97, M+ꢀ
138].
Acknowledgements
The authors gratefully acknowledge the partial support of this study by Ferdowsi University of
Mashhad Research Council (Grant no. p/3/32111).
Notes and references
Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Mashhad 9177948974, Iran.
* Corresponding author: Phone: +98ꢀ51ꢀ3880ꢀ5527, Fax: +98ꢀ51ꢀ3879ꢀ5457,
Eꢀmail: akhlaghinia@um.ac.ir
Electronic Supplementary Information (ESI) available: [details of any supplementary
information available should be included here].
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