UV365 light promoted catalyst-free synthesis of pyrimido[4,5-b] quinoline-2,4-diones in aqueous-glycerol medium

Article abstract of DOI:10.1039/c8nj01459k

Herein, a highly efficient and environmentally benign protocol for the synthesis of biologically important pyrimido[4,5-b]quinolinone-2,4-diones from aromatic amines, barbituric acid and aryl aldehyde is reported. This process takes place at room temperat

Full text of DOI:10.1039/c8nj01459k

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PAPER
Jason B. Benedict et al.
The role of atropisomers on the photo-reactivity and fatigue of
diarylethene-based metal–organic frameworks
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ARTICLE
UV light promoted catalyst-free synthesis of pyrimido[4,5-
365
b]quinoline-2,4-diones in aqueous-glycerol medium.
Received 00th January 20xx,
Accepted 00th January 20xx
a,b,†
a,†
c
Geetmani Singh Nongthombam,
George Kupar Kharmawlong, John Elisa Kumar, and
a
Rishanlang Nongkhlaw *
DOI: 10.1039/x0xx00000x
A highly efficient and environment benign protocol for the synthesis of biologically
important pyrimido[4,5-b]quinolinone-2,4-diones from aromatic amines, barbituric acid
and aryl aldehyde is reported herein. This process operates at room temperature under
direct irradiation from UV365 light source in the absence of a photocatalyst. The reported
approach demonstrates several merits such as high yield, clean reaction condition,
chromatography-free synthesis and use of cheap water-glycerol solvent system which is
also an environment friendly solvent. The applicability of this protocol for large-scale
synthesis of pyrimido[4,5-b]quinolinone-2,4-diones without wasting any expensive
www.rsc.org/
chemical is an added advantage.
photocatalysts come in the form of complex expensive systems so
explorations are still going strong on developing cheaper
alternatives. UV365 bridges the gap between the high-energy UV295
and photocatalyst-dependent visible light reactions. Based on the
prospect of carrying out organic transformations using UV365 under
Introduction
Light has always been an essential element in the universe and is
fundamental for the survival of mankind. The importance and
influence of light in several scientific discoveries has been catalyst-free condition, we envisioned several synthetic routes
acknowledged by the United Nations by declaring the year 2015 as which would lead to pharmaceutically important heterocyclic
compounds.
the International Year of Light and Light-based Technologies.
Pyrimido[4,5-b]quinolinone-2,4-diones are an important class of
Photocatalysis,
a catalytic technique which came into
th
heterocyclic compounds (Fig. 1) which possesses profound
significance in the latter half of the 20 century has been regarded
as a cutting edge discovery in the field of green chemistry
2
1–26
1–6
biological activities
viz. anti-malarial, anti-bacterial, analgesic,
.
anti-tumor, etc. They have also found applications in the synthesis
of electroluminescent materials, due to their high fluorescent
Furthermore, photocatalysis gives rise to amazing and often
unusual reaction pathways not commonly observed in reactions
performed in the absence of light. Many researchers have
2
7–30
activity
pyrimidine starting material
compounds was also prepared via. MCR mixture of aldehydes,
. Its derivatives were previously synthesized from
3
1–37
7
–14
. Subsequently, this class of
reported
the use of UV295 in photocatalytic degradation of dyes
and complex organic structures; however, it is not environment
friendly and poses detrimental effect on human health. On the
contrary, UV365 which lies in the region adjacent to the visible light
in the electromagnetic spectrum is environmentally benign. The use
of visible light has been proposed by many concerned chemists as a
catalyst alternative but, most organic compounds do not
themselves absorb in the visible region and so UV is a powerful
3
8–40
anilines, and tetronic acid
. In the later years, Aknin et al.
successfully synthesized 5-arylpyrimido[4,5-b]quinoline-2,4-(1H,
41
3
H)-dione derivatives by replacing tetronic acid with barbituric
acid and this protocol was further refined by Panahi and co-
42
workers by using L-proline as the catalyst; however, no reports on
its preparation under photocatalytic condition have been found till
date.
3
65
1
5
alternative for such cases. When visible light is employed,
complicated strategies must be designed which allows efficient
transfer of energy from visible light to the involved organic systems.
This novel approach can be achieved through the use of
photosensitizers/photocatalysts, which possesses the proficiency to
either pass on energy directly to the concerned organic molecules
or engage in single-electron transfer via. their photoexcited states
O
OOC
COO
NH
NH
O
HO
N
N
O
5-Deazaflavin
O
OH
COO
O
OH
HN
1
6–20
HO
NH
which is based on photoredox activation phenomena
. These
O
Coenzyme F420
O
P
O
N
N
O
O
CH3
H
Fig. 1 Some biologically important pyrimido[4,5-b]quinolone-2,4-
diones.
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was dispersed in water-glycerol and irradiated for 15 minutes. It
was then followed by slow addition of aryl aldehyde into the
solution and further irradiation for another 45 minutes. The whole
process was conducted under continuous bubbling (air) condition
so as to avoid any unreacted starting material residues.
Results and discussion
Our present work involves synthesis of several pyrimido[4,5-
b]quinolone-2,4-dione derivatives by exposing
a mixture of
barbituric acid, aryl amines and aryl aldehydes to long ultraviolet
light (i.e. UV365). The proposed system could be realized only in the
presence of a suitable solvent for thorough dispersion of the
reactant molecules. Initially, water was selected as an ideal eco-
friendly medium for our system and the yield of the product
obtained was also found to be in good amount; however, the
reaction mixture required longer exposure time and more number
of lamps had to be employed. The solvent system was further
tested with a series of solvent combinations and it was found that a
mixture of water and glycerol (1:1) exhibited promising results. For
O
R1
HN
N
R
O
N
O
R
H
Aldehyde-barbituric acid
Aldehyde-aniline
this solvent system, the photocatalytic process required only eight Fig. 2 Intermediate products formed under normal circumstances
lamps and the yield was much better than the water mediated
system. Meanwhile, the photocatalytic process was also tried with
The completion of the reaction could be easily monitored by the
ethanol medium but it did not show any productivity instead
change in the color of the reaction medium as well as from the
unwanted intermediates were formed. Here, the choice of solvents
appearance of solid precipitates (Fig. 3). Initially, the mixture of
was restricted to only the eco-friendly ones. In addition to the
barbituric acid and aryl amine dissolves in water-glycerol medium
solvent studies, the reaction was also screened (Table 1.) for the
on exposure to the UV365 lamps under continuous bubbling
possibility of preparing the target molecules under conventional
condition.
conditions (room temperature stirring, reflux, ultrasound, etc.) but
it always ended with intermediate products.
Table 1 Solvent and condition optimization for the synthesis of 4a.
a
b
a
Reaction
Time(hr)
Yield
(%)
Solvent
Condition
Water
RT Stirring
RT Stirring
7
7
0
0
Water-glycerol
Fig. 3 (a) Barbituric acid and aniline mixture after 15 minutes of
UV365 irradiation. (b) Barbituric acid, aniline and benzaldehyde after
RT Stirring
Ethanol
Water
7
7
0
0
4
5 minutes UV365 irradiation.
Reflux
Reflux
Water-glycerol
Ethanol
7
7
0
0
The product was recovered by simple filtration and the residue was
washed several times with warm water so as to remove any glycerol
remnants.
Reflux
Water
Ultrasound
Ultrasound
2
2
0
0
Water-glycerol
b
a
Ethanol
Water
Ultrasound
2
0
UV365 irradiation (8 lamps)
2
1
1
66
98
0
Cooling Fan
UV254
Water-glycerol UV365 irradiation (8 lamps)
Ethanol UV365 irradiation (8 lamps)
RT= room temperature; a=observed yield of 4a
Air Pump
Cooling
Fan
Cooling
Fan
UV365
Cooling Fan
The one-pot reaction of barbituric acid with aryl amines and aryl
aldehydes always resulted in unwanted intermediate products.
The two kinds of intermediates which were normally formed were Fig. 4 (a) Graphical diagram of the Multi-Lamp photoreactor.
aldehyde-barbituric acid intermediate and aldehyde-aniline
intermediate (Fig. 2). In order to avoid the formation of the
intermediates, we fragmented the continuous one hour photo-
irradiation into two parts: Firstly, barbituric acid and aryl amine
(
b) Multi-Lamp photoreactor instrument.
2
| J. Name., 2012, 00, 1-3
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R
CHO
O
NH2
O
HN
UV365 Irradiation
R1
+
+
HN
O
N
H
O
H O-glycerol
2
R1
R
O
N
H
N
H
1
2a-e
3
a-j
4
a-x
Scheme 1. Synthesis of pyrimido[4,5-b]quinoline-2,4-dionederivatives under UV365 irradiation.
Table 2 Pyrimido[4,5-b]quinoline-2,4-dione derivatives synthesized via. Scheme 1.
o
Entry
R
H
R
1
Time (mins)
Yield (%) Melting Point ( C)
a
b
4
a
b
H
H
60
60
60
60
60
60
90
60
60
90
60
90
90
90
60
90
90
90
60
90
90
90
98
95
93
94
90
90
87
97
91
88
95
89
85
90
93
87
93
91
96
91
87
88
224-226 , 225-230
a
4
4-F
196-198
a
4
c
3-Br
4-Br
4-NO
2-Cl
2-Cl
H
H
200-202
a
4
d
e
H
218-220
a
4
2
H
231-233
a
4
f
H
204-206
a
4
4
g
4-CH3
4-OCH
H
184-186
a
h
190-192
3
a
4
4
i
j
4-CH
3
180-182
a
4-CH3
4-NO2
3-Cl
4-CH3
200-201
a
4
k
4-OCH3
4-CH3
4-Cl
231-233
a
4
l
270-272
a
4
m
2-Cl
186-188
a
4
n
o
p
q
3-Br
4-CH
3
>300
a
4
4-CH
4-Cl
3-F
3
4-OCH
3
197-199
a
4
4
4-CH
H
3
3
218-220
a
198-200
a
4r
4s
4t
3-F
4-CH
>300
a
4-F
4-OCH
4-Br
3
194-196
a
4-NO
2
238-240
a
4
u
v
4-F
4-CH
3
204-206
a
4
2-Cl
4-Br
193-195
a
4
w
3-Cl
4-Cl
H
H
60
60
85
93
202-204
a
4
x
194-196
4
2
a = found; b= reported
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The multi-lamp photoreactor comprises of twelve UV365 lamps and acid, aryl amine and aryl aldehyde proceeds via. aldehyde-barbituric
several combinations are possible for the lamps i.e. 2,4,6,8 and 12 acid intermediate which then reacts with the aryl amine moiety. It
(Fig. 4). The intensity of each combination was also recorded using must be noted that they employed L-proline as catalyst for the
a photometer and the details are given in Table 3.
process and it corroborates their proposed mechanism. However, in
our catalyst-free reaction condition, the aldehyde-barbituric acid
intermediate did not show any tendency to react further with the
aryl amine moiety. In order to determine, whether our reaction
proceeds via radical pathway or simple condensation pathway, we
performed a small set of experiment. Here, firstly a mixture of
barbituric acid and aniline was exposed to UV365 for 15 minutes and
Table 3 Intensity of UV365 with respect to the number of lamps
Intensity corresponding to the
Number of UV365 Lamps
-2
lamps(µWcm )
2
4
6
8
1260
1803
3840
4590
6940
1
the byproduct was isolated and upon characterization by H-NMR
spectroscopy it was found to be IS
1
. Next, we repeated the same
reaction condition in the presence of H O which is a precursor of
2
2
hydroxyl radical, a radical inhibitor. It was observed that in the
presence of the radical inhibitor, our expected intermediate IS was
1
not formed. A mixture of aniline and alloxan was isolated from the
reaction mixture. We did some literature survey and further verified
that alloxan is indeed formed by reaction of hydroxyl radical with
12
4
3
barbituric acid under Fenton condition . Since the presence of
radical inhibiting hydroxyl radical prohibits the formation of our
Our model reaction for the synthesis of 4a was tested with all the
possible lamp combinations and we also varied the solvent system
in order to estimate the efficiency of the system (Table 4). It was
found that the water-glycerol system gave the best yield on
exposure to 8 UV365 lamps. In the case of water mediated system,
the optimum number of lamps required for best yield was found to
be 12. Considering the optimum number of lamps and product
yield, water-glycerol was selected to be the better choice over
water system. This protocol was extended to several substituted
aryl amines and aryl aldehydes (Scheme 1). The substituted aryl
aldehydes did not exhibit much variation in the yield of the product;
however, an interesting observation was made when substituted
aryl amines were used. When strong electron donating substituent
1
desired intermediate (IS ), we concluded that barbituric acid and
aniline does not undergo simple condensation but follow radical
pathway. After considering the outcome of this experimental
study, we concluded that under photocatalytic condition our
reaction follows a radical pathway leading to aniline-barbituric acid
intermediate which further reacts with aldehyde to yield our target
molecule. Finally, a probable mechanism involving free radicals was
conceptualized (Scheme 2).
(
such as OCH
product yield was slightly higher as compared to other substituents
Table 2). In order to compensate this setback for the other
3
) was present in the aryl ring of the amine, the
(
substituted aryl amines, the irradiation time was increased to 1.5
hours for aryl amines with substituents other than methoxy group.
Table 4 Optimization of UV365 intensity by varying the number of
lamps for the synthesis of 4a under different conditions.
a
Number Reaction Yield
Solvent
Condition
of lamps Time (hr) (%)
Water
UV365 irradiation
2
2
1
1
1
1
1
1
1
1
1
0
Water-glycerol UV365 irradiation
Water UV365 irradiation
Water-glycerol UV365 irradiation
Water UV365 irradiation
Water-glycerol UV365 irradiation
Water UV365 irradiation
Water-glycerol UV365 irradiation
Water UV365 irradiation
0
4
10
27
30
65
60
98
75
4
6
6
8
8
12
Water-glycerol UV365 irradiation
12
1
98
a=observed yield of 4a
4
2
Scheme 2. Proposed mechanism for UV365 aided synthesis of 4a via.
As per Nezhad and co-workers , the mechanism for the synthesis
free radical pathway.
of pyrimido[4,5-b]quinoline-2,4-dione derivatives from barbituric
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Initially, free radical is generated from the carbonyl of the was recovered by simple filtration followed by washing with warm
barbituric acid on photo-irradiation which then interacts with Millipore water and drying.
the -NH group of the aryl amine moiety. During the process
the aryl aldehyde also generates a free radical on photo
Conclusions
irradiation and participates in the free radical interactions. The
In summary, a green, efficient and environmentally benign UV365
2
hydrogen exchange which takes place in IS is being facilitated
light mediated synthesis of several pyrimido[4,5-b]quinolinone-2,4-
dione derivatives was successfully carried out under water-glycerol
medium. The merits and novelty of this process does not end here;
it can be further investigated for the synthesis of numerous classes
of heterocycles. The ease of operation of the protocol under clean
and simple column-free work up condition is worth mentioning.
by a six membered transition state (TS1) thereby leading to IS3
In the final step, IS undergoes tautomerization so as to
.
4
recover the aromaticity of the third ring leading to our target
molecule.
Table 5 Ecoscale based comparison for the synthesis of 4a as per
4
2
UV365 protocol and L-proline protocol .
Acknowledgements
Parameter Penalty points
The authors would like to acknowledge Dr. M. K. Sahoo for
allowing access to the UV reactor system. Analytical assistance
from SAIF-NEHU and Department of Chemistry-NEHU is highly
appreciated.
UV365
L-proline
1
2
. Yield
1
5.5
. Price of reaction components
Inexpensive (< $10)
0
0
0
0
Analytical data of synthesised compounds:
a
3
4
. Safety
5-phenyl-5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H,3H)-dione
o
(
1
4a): Yield: 98%; Melting point: 224-226 C; IR (KBr): ν 3335, 3025,
Safe for environment
. Technical setup
Common setup
–1 1
690, 1619, 1495, 1409, 1123, 780, 556 cm ; H-NMR (400 MHz,
): δ 11.15 (s, 1H), 10.17 (bs, 2H), 8.10 (d, 1H, J = 7.2Hz),
.47-7.56 (m, 1H), 7.33-7.35 (m, 2H), 7.04-7.18 (m, 5H), 5.93 (s, 1H);
DMSO-D
6
7
-
0
-
13
C-NMR (100 MHz, DMSO-D
133.0, 129.5, 128.8, 127.4, 126.6, 125.2, 124.4, 120.9, 91.6, 30.6.
Anal. Calcd. for C17 : C, 70.09; H, 4.50; N, 14.42%; Found: C,
6
): δ 167.7, 161.5, 150.6, 144.2, 135.7,
Unconventional
activation technique
b
2
13 3 2
H N O
7
5
0.25; H, 4.45; N, 14.29%.
-(4-fluorophenyl)-5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H,
5
. Temperature/time
o
Room temperature, < 1 h
Heating, > 1 h
0
-
-
3H)-dione (4b): Yield: 95%; Melting point: 196-198 C; IR (KBr): ν
–1 1
3
(
375, 3033, 1687, 1622, 1505, 1402, 1124, 776, 557 cm ; H-NMR
400 MHz, DMSO-D ): δ 11.25 (s, 1H), 10.11 (bs, 2H), 7.30-7.23 (m,
3H), 7.03-6.99 (m, 4H), 6.95-6.91 (m, 1H), 5.88 (s, 1H); C-NMR
100 MHz, DMSO-D ): δ 165.1, 160.8, 158.7, 150.8, 140.3, 136.9,
32.6, 129.4, 128.2, 128.1, 124.2, 120.2, 113.7, 91.9, 30.1. Anal.
Calcd. for C17 : C, 66.02; H, 3.91; N, 13.59%; Found: C,
6.19; H, 3.84; N, 13.66%.
3
6
13
6
. Workup and purification
Simple filtration
(
1
6
0
0
Ecoscale score
100-3 = 97 100-8.5 = 91.5
3 2
H12FN O
6
5
3
3
-(3-bromophenyl)-5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H,
Experimental
o
H)-dione (4c): Yield: 93%; Melting point: 200-202 C; IR (KBr): ν
–1 1
356, 3032, 1690, 1615, 1487, 1389, 1125, 780, 557 cm ; H-NMR
): δ 11.11 (s, 1H), 10.16 (s, 2H), 7.42-7.34 (m,
All the chemicals involved in the synthesis were purchased from
Alfa Aesar, Sigma-Aldrich & Merck and were used without further
purification. The purity of the products was confirmed by infrared
FT-IR), H-NMR, and C-NMR. FT-IR spectra were recorded in KBr
pellets on a Perkin Elmer Spectrum 400 FTIR instrument, and the
frequencies are expressed in cm . H-NMR and C-NMR spectra
were recorded on a BrukerAvance II-400 spectrometer in DMSO-d
chemical shifts in δ). Elemental analyses were carried out on a
Heraeus CHN-O-Rapid analyzer. The UV365 irradiation was
conducted in a UV reactor fitted with twelve lamps (8W each) of
Herber Scientific make; model HML, Compact-LP-MP-812.
(
400 MHz, DMSO-D
6
13
2
H), 7.23-7.09 (m, 5H), 7.01 (d, 1H, J = 7.6Hz), 5.91 (s, 1H); C-NMR
): δ 167.7, 159.8, 150.5, 147.7, 142.2, 134.8,
29.6, 129.5, 129.2, 127.3, 125.8, 123.0, 121.1, 109.1, 91.1, 30.6.
: C, 55.15; H, 3.27; N, 11.35%; Found:
(
100 MHz, DMSO-D
6
1
13
(
1
Anal. Calcd. for C17
C, 55.28; H, 3.34; N, 11.19%.
5
3
3
3 2
H12BrN O
-1
1
13
6
-(4-bromophenyl)-5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H,
(
o
H)-dione (4d): Yield: 94%; Melting point: 218-220 C; IR (KBr): ν
–1 1
376, 3021, 1691, 1614, 1478, 1405, 1126, 778, 555 cm ; H-NMR
): δ 11.26 (s, 1H), 10.12 (bs, 2H), 7.65 (d, 2H, J =
.8Hz), 7.37-7.25 (m, 3H), 7.13-7.08 (m, 2H), 6.95 (d, 1H, J = 8.4Hz),
(
400 MHz, DMSO-D
6
8
1
3
General procedure for preparation of 4a-x:
5.86 (s, 1H); C-NMR (100 MHz, DMSO-D
6
): δ 163.2, 159.6, 150.5,
50.1, 144.0, 134.6, 131.8, 130.9, 130.1, 129.5, 129.0, 126.2, 125.2,
20.9, 117.3, 91.3, 30.4. Anal. Calcd. for C17 : C, 55.15; H,
.27; N, 11.35%; Found: C, 54.96; H, 3.25; N, 11.43%.
1
1
3
5
3
3
5
2
In a 100 ml borosilicate tube, barbituric acid (1mmol), aromatic
amine (1 mmol) and 30ml of Millipore water-glycerol (50:50) was
irradiated by 8 lamps of UV365 source for 15 minutes under
continuous air-bubbling condition; then aryl aldehyde (1 mmol) was
charged into the solution and further irradiated by 8 lamps of UV365
for another 45-75 minutes. On completion of the reaction
H
3 2
12BrN O
-(4-nitrophenyl)-5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H,
o
H)-dione (4e): Yield: 90%; Melting point: 231-233 C; IR (KBr): ν
387, 2999, 1692, 1622, 1496, 1412, 1346, 1227, 1111, 849, 779,
–1 1
56 cm ; H-NMR (400 MHz, DMSO-D ): δ 11.12 (s, 1H), 10.20 (s,
(
indicated by appearance of thick solid precipitate), the precipitate
6
H), 8.03-8.05 (m, 2H), 7.39-7.43 (m, 2H), 7.20-7.27 (m, 4H), 6.03 (s,
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1
3
1
1
H); C-NMR (100 MHz, DMSO-D ): δ 168.7, 160.0, 154.0, 150.5,
H-NMR (400 MHz, DMSO-D ): δ 11.11 (s, 1H), 10.09 (bs, 2H), 7.21-
6
6
1
44.9, 134.0, 129.6, 127.8, 126.4, 123.9, 122.8, 121.8, 90.2, 31.3. 7.15 (m, 3H), 7.10-7.06 (m, 3H), 6.95 (d, 1H, J = 7.6Hz), 5.92 (s, 1H),
1
3
Anal. Calcd. for C H N O : C, 60.71; H, 3.60; N, 16.66%; Found: C, 2.27 (s, 3H); C-NMR (100 MHz, DMSO-D ): δ 163.5, 161.5, 150.5,
1
7
12
4
4
6
60.58; H, 3.63; N, 16.72%.
147.5, 136.5, 132.2, 130.2, 130.0, 129.3, 126.2, 125.4, 124.4, 122.2,
5
-(2-chlorophenyl)-5,10-dihydropyrimido[4,5-b]quinoline-
117.0, 90.2, 30.5, 20.4. Anal. Calcd. for C H ClN O : C, 63.63; H,
18
14
3 2
o
2,4(1H,3H)-dione (4f): Yield: 90%; Melting point: 204-206 C; IR 4.15; N, 12.37%; Found: C, 63.72; H, 4.11; N, 12.29%.
–1 1
(KBr): ν 3345, 3019, 1697, 1617, 1405, 1121, 780, 558 cm ; H-NMR 7-chloro-5-(2-chlorophenyl)-5,10-dihydropyrimido[4,5-b]quinoli
o
(
7
(
1
3
400 MHz, DMSO-D
.2Hz), 7.29-7.25 (m, 3H), 7.08-6.97 (m, 4H), 5.78 (s, 1H); C-NMR (KBr): ν 3334, 3021, 1691, 1405, 1122, 778, 554 cm ; H-NMR (400
100 MHz, DMSO-D ): δ 168.2, 164.8, 151.1, 150.6, 142.6, 137.3, MHz, DMSO-D ): δ 11.11 (s, 1H), 10.19 (bs, 2H), 7.73 (d, 1H, J =
33.1, 132.3, 130.6, 129.9, 129.5, 126.9, 126.0, 124.8, 120.8, 80.0, 7.2Hz), 7.45 (t, 1H, J = 7.2Hz), 7.35 (t, 1H, J = 7.4Hz), 7.26-7.19 (m,
6
): δ 11.12 (s, 1H), 10.01 (bs, 2H), 7.74 (d, 1H, J = ne-2,4(1H,3H)-dione (4m): Yield: 85%; Melting point: 186-188 C; IR
1
3
–1 1
6
6
13
3 2
1.4. Anal. Calcd. for C17H12ClN O : C, 62.68; H, 3.71; N, 12.90%; 1H), 7.15-7.04 (m, 2H), 6.74 (d, 1H, J = 8.8Hz), 5.72 (s, 1H); C-NMR
Found: C, 62.79; H, 3.67; N, 12.82%.
-(2-chlorophenyl)-7-methyl-5,10-dihydropyrimido[4,5-b]quinoli
(100 MHz, DMSO-D ): δ 163.1, 161.3, 151.0, 150.1, 140.9, 132.3,
130.7, 129.4, 129.3, 127.1, 126.7, 126.1, 125.1, 122.2, 119.9, 91.5,
6
5
o
ne-2,4(1H,3H)-dione (4g): Yield: 87%; Melting point: 184-186 C; IR 31.8. Anal. Calcd. for C H Cl N O : C, 56.69; H, 3.08; N, 11.67%;
1
7
11
2 3 2
–
1
(
KBr): ν 3363, 3022, 1689, 1624, 1467, 1384, 1124, 781, 559 cm ; Found: C, 56.49; H, 3.12; N, 11.74%.
1
6
H-NMR (400 MHz, DMSO-D ): δ 11.12 (s, 1H), 9.99 (bs, 2H), 7.74 (d, 5-(3-bromophenyl)-7-methyl-5,10-dihydropyrimido[4,5-b]quinoli
o
1
2
1
1
C
H, J = 7.6Hz), 7.27-7.16 (m, 3H), 7.14-7.10 (m, 1H), 7.07-7.03 (m, ne-2,4(1H,3H)-dione (4n): Yield: 90%; Melting point: >300 C; IR
1
3
–1 1
H), 5.80 (s, 1H), 2.26 (s, 3H); C-NMR (100 MHz, DMSO-D
68.2, 164.9, 151.1, 150.7, 142.6, 136.0, 133.6, 133.1, 130.0, 130.6, NMR (400 MHz, DMSO-D
30.4, 129.5, 126.9, 126.0, 122.1, 90.2, 31.3, 20.9. Anal. Calcd. for (m, 1H), 7.23-7.21 (m, 2H), 7.14-7.09 (m, 3H), 7.00 (d, 1H, J = 8Hz),
6
): δ (KBr): ν 3352, 3043, 1688, 1621, 1396, 1121, 851, 780, 557 cm ; H-
6
): δ 11.11 (s, 1H), 10.12 (bs, 2H), 7.43-7.37
1
3
18
H
14ClN
3
O
2
: C, 63.63; H, 4.15; N, 12.37%; Found: C, 63.77; H, 4.09; 5.92 (s, 1H), 2.27 (s, 1H); C-NMR (100 MHz, DMSO-D
161.5, 150.5, 147.8, 136.6, 130.1, 130.0, 129.6, 129.1, 127.3, 125.8,
122.3, 121.1, 90.3, 30.5, 20.4. Anal. Calcd. for C18 : C,
1H,3H)-dione (4h): Yield: 97%; Melting point: 190-192 C; IR (KBr): 56.27; H, 3.67; N, 10.94%; Found: C, 56.00; H, 3.58; N, 11.17%.
6
): δ 163.2,
N, 12.44%.
-methoxy-5-phenyl-5,10-dihydropyrimido[4,5-b]quinoline-2,4
7
(
3 2
H14BrN O
o
–
1
ν 3310, 3133, 2960, 1693, 1606, 1493, 1404, 1251, 778, 555 cm ; 7-methoxy-5-(p-tolyl)-5,10-dihydropyrimido[4,5-b]quinoline-2,4
1
o
H-NMR (400 MHz, DMSO-D
.10 (m, 4H), 7.01-6.95 (m, 4H), 5.94 (s, 1H), 3.73 (s, 3H); C-NMR ν 3339, 3027, 1698, 1618, 1408, 1225, 780, 554 cm ; H-NMR (400
100 MHz, DMSO-D ): δ 167.8, 158.3, 158.0, 157.9, 150.6, 136.2, MHz, DMSO-D ): δ 11.11 (s, 1H), 9.99 (s, 2H), 7.09 (d, 2H, J = 8.8Hz),
31.0, 128.7, 128.3, 127.3, 126.6, 125.5, 122.3, 114.7, 114.3, 90.9, 6.97-6.86 (m, 5H), 5.88 (s, 1H), 3.71 (s, 3H), 2.18 (s, 3H); C-NMR
5.2, 30.4. Anal. Calcd. for C18 : C, 67.28; H, 4.71; N, 13.08%; (100 MHz, DMSO-D ): δ 158.6, 158.1, 151.1, 144.5, 141.9,
133.4,129.8, 128.4, 127.0, 123.7, 122.7, 115.2, 91.5, 55.7, 30.5,
20.9. Anal. Calcd. for C19 : C, 68.05; H, 5.11; N, 12.53%;
ne (4i): Yield: 91%; Melting point: 180-182 C; IR (KBr): ν 3350, Found: C, 67.88; H, 5.03; N, 12.70%.
6
): δ 11.13 (s, 1H), 10.06 (bs, 2H), 7.18- (1H,3H)-dione (4o): Yield: 93%; Melting point: 197-199 C; IR (KBr):
1
3
–1 1
7
(
1
5
6
6
13
H
15
N
3
O
3
6
Found: C, 67.36; H, 4.68; N, 13.15%.
-(p-tolyl)-5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H,3H)-dio
5
17 3 3
H N O
o
–1 1
3120, 2960, 1667, 1408, 1231, 778, 557 cm ; H-NMR (400 MHz, 5-(4-chlorophenyl)-7-methyl-5,10-dihydropyrimido[4,5-b]quinoli
o
DMSO-D
.22-7.18 (m, 2H), 6.93-6.87 (m, 4H), 5.84 (s, 1H), 2.36 (s, 3H); C- (KBr): ν 3329, 3017, 2945, 1697, 1398, 1225, 780, 557 cm ; H-NMR
NMR (100 MHz, DMSO-D ): δ 163.5, 161.7, 150.5, 143.4, 141.1, (400 MHz, DMSO-D ): δ 11.11 (s, 1H), 10.07 (bs, 2H), 7.20-7.16 (m,
37.8, 133.9, 133.0, 129.8, 129.3, 128.8, 127.9, 126.5, 123.5, 119.7, 3H), 7.07 (d, 2H, J = 8Hz), 6.99 (d, 2H, J = 8.4Hz), 5.89 (s, 1H), 2.26 (s,
6
): δ 11.34 (s, 1H), 10.04 (bs, 2H), 7.28 (d, 2H, J = 8.4Hz), ne-2,4(1H,3H)-dione (4p): Yield: 87%; Melting point: 218-220 C; IR
13
–1 1
7
6
6
1
9
1
13
1.0, 30.3, 21.3. Anal. Calcd. for C18
3.76%; Found: C, 70.90; H, 5.01; N, 13.68%.
3 2
-methyl-5-(p-tolyl)-5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H, 20.4. Anal. Calcd. for C18H14ClN O
H
15
N
3
O
2
: C, 70.81; H, 4.95; N, 3H); C-NMR (100 MHz, DMSO-D
136.1, 130.7, 130.0, 128.8, 128.5, 128.0, 127.2, 122.0, 90.5, 30.2,
: C, 66.63; H, 4.15; N, 12.37%;
6
): δ 164.9, 160.7, 150.6, 143.6,
7
o
3H)-dione (4j): Yield: 88%; Melting point: 200-201 C; IR (KBr): ν Found: C, 63.83; H, 4.07; N, 12.12%.
–1 1
3345, 3038, 2957, 1676, 1411, 1225, 780, 556 cm ; H-NMR (400 5-(3-fluorophenyl)-5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H,
o
MHz, DMSO-D
6
): δ 11.11 (s, 1H), 10.00 (bs, 2H), 7.1 (d, 2H, J = 8Hz), 3H)-dione (4q): Yield: 93%; Melting point: 198-200 C; IR (KBr): ν
13
–1 1
6.93-6.86 (m, 5H), 5.87 (s, 1H), 2.22 (s, 3H), 2.18 (s, 3H); C-NMR 3367, 3024, 1686, 1619, 1398, 1122, 778, 554 cm ; H-NMR (400
(
100 MHz, DMSO-D
6
): δ 163.6, 161.8, 150.6, 150.2, 141.2, 134.9, MHz, DMSO-D
6
): δ 11.11 (s, 1H), 10.16 (bs, 2H), 7.37-7.33 (m, 2H),
13
1
3
1
32.9, 132.3, 129.9, 129.3, 128.8, 128.5, 127.9, 126.5, 121.2, 90.9, 7.19-7.13 (m, 3H), 6.85-6.70 (m, 3H), 5.90 (s, 1H); C-NMR (100
0.1, 21.3, 20.4. Anal. Calcd. for C19
3.16%; Found: C, 71.55; H, 5.43; N, 13.08%.
-methoxy-5-(4-nitrophenyl)-5,10-dihydropyrimido[4,5-b]quinoli
H
17
N
3
O
2
: C, 71.46; H, 5.37; N, MHz, DMSO-D
6
): δ 164.4, 163.3, 160.9, 150.5, 147.9, 134.8, 129.5,
129.1, 129.0, 125.8, 122.7, 121.4, 118.3, 113.0, 111.2, 90.3, 30.7.
Anal. Calcd. for C17 : C, 66.02; H, 3.91; N, 13.59%; Found: C,
ne-2,4(1H,3H)-dione (4k): Yield: 95%; Melting point: 231-233 C; IR 66.23; H, 4.02; N, 13.38%.
7
3 2
H12FN O
o
–1
(
KBr): ν 3413, 3037, 2965, 1699, 1619, 1398, 1254, 780, 554 cm ; 5-(3-fluorophenyl)-7-methyl-5,10-dihydropyrimido[4,5-b]quinoline
1
o
H-NMR (400 MHz, DMSO-D
6
): δ 11.13 (s, 1H), 10.16 (bs, 2H), 8.05 -2,4(1H,3H)-dione (4r): Yield: 91%; Melting point: >300 C; IR (KBr):
–1 1
(d, 2H, J = 8.4Hz), 7.24-7.26 (m, 3H), 7.02 (d, 2H, J = 8.8Hz), 6.04 (s, ν 3365, 3057, 2957, 1698, 1614, 1412, 1125, 779, 553 cm ; H-NMR
13
1
1
9
1
H), 3.75 (s, 3H); C-NMR (100 MHz, DMSO-D
6 6
): δ 167.4, 161.2, (400 MHz, DMSO-D ): δ 11.11 (s, 1H), 10.09 (bs, 2H), 7.22-7.08 (m,
58.5, 154.0, 150.6, 144.9, 135.4, 131.2, 127.7, 124.2, 122.8, 114.7, 4H), 6.84-6.82 (m, 2H), 6.71-6.68 (m, 1H), 5.92 (s, 1H), 2.27 (s, 3H);
1
3
0.4, 55.3, 31.2. Anal. Calcd. for C18
5.29%; Found: C, 58.91; H, 3.86; N, 15.35%.
-(3-chlorophenyl)-7-methyl-5,10-dihydropyrimido[4,5-b]quinoli
H
14
N
4
O
5
: C, 59.02; H, 3.85; N,
6
C-NMR (100 MHz, DMSO-D ): δ 168.2, 163.8, 161.4, 151.0, 148.6,
137.0, 130.8, 130.5, 129.6, 129.5, 123.2, 122.7, 113.7, 111.5, 91.0,
31.1, 20.9. Anal. Calcd. for C H FN O : C, 66.87; H, 4.36; N,
5
1
8
14
3 2
o
ne-2,4(1H,3H)-dione (4l): Yield: 89%; Melting point: 270-272 C; IR 13.00%; Found: C, 66.68; H, 4.27; N, 13.20%.
–1
(KBr): ν 3401, 3031, 2950, 1687, 1623, 1406, 1122, 789, 552 cm ;
6
| J. Name., 2012, 00, 1-3
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Pl Ne ae swe Jd oo u nr no at l aod fj Cu sh te mm ai sr tgr iyn s
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DOI: 10.1039/C8NJ01459K
Journal Name
-(4-fluorophenyl)-7-methoxy-5,10-dihydropyrimido[4,5-b]quinoli
ARTICLE
5
4
5
M. Oelgemöller, C. Jung and J. Mattay, Pure Appl. Chem., 2007,
79, 1939–1947.
P. Esser, B. Pohlmann and H.-D. Scharf, Angew. Chemie Int. Ed.
English, 1994, 33, 2009–2023.
G. Ciamician, Science, 1912, 36, 385–394.
M. K. Sahoo, M. Marbaniang, B. Sinha, D. B. Naik and R. N.
Sharan, Chem. Eng. J., 2012, 213, 142–149.
T. Egerton, Molecules, 2014, 19, 18192–18214.
B. Ghasemi, B. Anvaripour, S. Jorfi and N. Jaafarzadeh, Int. J.
Photoenergy, 2016, 2016, 1–10.
o
ne-2,4(1H,3H)-dione (4s): Yield: 96%; Melting point: 194-196 C; IR
–
1 1
(
KBr): ν 3387, 3032, 1695, 1617, 1397, 1123, 780, 558 cm ; H-
NMR (400 MHz, DMSO-D ): δ 11.12 (s, 1H), 10.06 (bs, 2H), 7.18 (d,
H, J = 8.8Hz), 7.00-6.90 (m, 5H), 5.90 (s, 1H), 3.73 (s, 3H); C-NMR
100 MHz, DMSO-D ): δ 168.2, 161.5, 159.1, 158.6, 151.1, 141.0,
33.4, 128.7, 125.8, 124.1, 122.8, 115.2, 114.4, 91.3, 55.8, 30.4.
: C, 63.71; H, 4.16; N, 12.38%; Found: C,
6
1
3
2
(
1
6
7
6
Anal. Calcd. for C18
H
14FN
3
O
3
8
9
6
7
2
3.56; H, 4.06; N, 12.45%.
-bromo-5-(4-nitrophenyl)-5,10-dihydropyrimido[4,5-b]quinoline-
o
,4(1H,3H)-dione (4t): Yield: 91%; Melting point: 238-240 C; IR 10 J. Jeong, K. Sekiguchi and K. Sakamoto, Chemosphere, 2004,
57, 663–671.
cm ; H-NMR (400 MHz, DMSO-D ): δ 11.32 (s, 1H), 10.30 (bs, 2H), 11 A. Gautam, A. Kshirsagar, R. Biswas, S. Banerjee and P. K.
(KBr): ν 3398, 3038, 1682, 1621, 1514, 1346, 1110, 851, 780, 554
–1 1
6
8
.06 (d, 2H, J = 8Hz), 7.40 (d, 2H, J = 16Hz), 7.26-7.32 (m, 1H), 6.90
Khanna, RSC Adv., 2016, 6, 2746–2759.
13
(d, 2H, J = 8Hz), 5.98 (s, 1H); C-NMR (100 MHz, DMSO-D ): δ 168.7, 12 R.-P. Qiao, N. Li, X.-H. Qi, Q.-S. Wang and Y.-Y. Zhuang, Toxicon,
6
1
1
2
5
61.0, 153.4, 150.5, 145.0, 137.9, 132.0, 129.7, 127.8, 123.9, 122.8,
2005, 45, 745–752.
21.5, 114.9, 91.9, 31.5. Anal. Calcd. for C17
.67; N, 13.49%; Found: C, 42.28; H, 2.71; N, 13.30%.
H
11BrN
4
O
4
: C, 49.18; H, 13 I. T. Peternel, N. Koprivanac, A. M. L. Božić and H. M. Kušić, J.
Hazard. Mater., 2007, 148, 477–484.
-(4-fluorophenyl)-7-methyl-5,10-dihydropyrimido[4,5-b]quinoline 14 M. K. Sahoo, B. Sinha and R. N. Sharan, Can. J. Chem. Eng.,
o
-
(
(
2,4(1H,3H)-dione (4u): Yield:87%; Melting point: 204-206 C; IR
KBr): ν 3375, 3018, 1689, 1614, 1409, 1124, 778, 553 cm ; H-NMR 15 K. Hölz, J. Lietard and M. M. Somoza, ACS Sustain. Chem. Eng.,
400 MHz, DMSO-D
2014, 92, 1693–1699.
–1 1
6
): δ 11.11 (s, 1H), 10.08 (bs, 2H), 7.18 (d, 2H, J =
2017, 5, 828–834.
8
3
1
3
1
7
Hz), 7.07 (d, 2H, J = 8Hz), 7.01-6.90 (m, 3H), 5.89 (s, 1H), 2.26 (s, 16 K. Zeitler, Angew. Chemie Int. Ed., 2009, 48, 9785–9789.
1
3
H); C-NMR (100 MHz, DMSO-D
6
): δ 167.7, 161.0, 158.6, 150.6, 17 F. Teplý, Collect. Czechoslov. Chem. Commun., 2011, 76, 859–
40.4, 135.7, 131.3, 129.9, 128.1, 126.5, 125.7, 121.7, 113.7, 90.8,
917.
0.0, 20.7. Anal. Calcd. for C18
3.00%; Found: C, 67.02; H, 4.44; N, 12.88%.
H
14FN
3
O
2
: C, 66.87; H, 4.36; N, 18 J. M. R. Narayanam and C. R. J. Stephenson, Chem. Soc. Rev.,
2011, 40, 102–113.
-bromo-5-(2-chlorophenyl)-5,10-dihydropyrimido[4,5-b]quinoline 19 J. W. Tucker and C. R. J. Stephenson, J. Org. Chem., 2012, 77,
o
-
(
(
2,4(1H,3H)-dione (4v): Yield: 88%; Melting point: 193-195 C; IR
KBr): ν 3374, 3017, 1689, 1618, 1406, 1125, 780, 556 cm ; H-NMR 20 J. Xuan and W.-J. Xiao, Angew. Chemie Int. Ed., 2012, 51, 6828–
400 MHz, DMSO-D
1617–1622.
–1 1
6
): δ 11.26 (s, 1H), 10.10 (bs, 2H), 7.74 (d, 1H, J =
6838.
7
.6Hz), 7.55 (d, 1H, J = 7.6Hz), 7.47 (t, 1H, J = 7.4Hz), 7.36 (t, 1H, J = 21 A. B. A. El-Gazzar, H. N. Hafez and G. A. M. Nawwar, Eur. J.
13
7.4Hz), 7.27-7.21 (m, 2H), 6.64 (d, 1H, J = 8.4Hz), 5.74 (s, 1H); C-
Med. Chem., 2009, 44, 1427–1436.
NMR (100 MHz, DMSO-D
6
): δ 163.1, 161.3, 150.6, 150.1, 143.4, 22 H. I. Ali, K. Tomita, E. Akaho, M. Kunishima, Y. Kawashima, T.
1
8
1
5
3
3
33.6, 132.7, 132.1, 130.7, 129.3, 127.0, 126.7, 126.1, 119.1, 110.9,
8.3, 31.8. Anal. Calcd. for C17H11BrClN O : C, 50.46; H, 2.74; N,
3 2
0.38%; Found: C, 50.58; H, 2.69; N, 10.27%.
Yamagishi, H. Ikeya and T. Nagamatsu, Eur. J. Med. Chem.,
2008, 43, 1376–1389.
23 H. I. Ali, K. Tomita, E. Akaho, M. Kunishima, Y. Kawashima, T.
Yamagishi, H. Ikeya and T. Nagamatsu, Eur. J. Med. Chem.,
2008, 43, 1376–1389.
-(3-chlorophenyl)-5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H,
o
H)-dione (4w): Yield: 85%; Melting point: 202-204 C; IR (KBr): ν
–1 1
353, 3032, 1689, 1625, 1399, 1121, 780, 557 cm ; H-NMR (400 24 H. I. Ali, K. Tomita, E. Akaho, H. Kambara, S. Miura, H.
MHz, DMSO-D
6
): δ 11.11 (s, 1H), 10.12 (bs, 2H), 7.34-7.30 (m, 2H),
Hayakawa, N. Ashida, Y. Kawashima, T. Yamagishi and H. Ikeya,
Bioorg. Med. Chem., 2007, 15, 242–256.
1
3
7.19-7.06 (m, 5H), 6.96 (d, 1H, J = 7.6Hz), 5.91 (s, 1H); C-NMR (100
6
MHz, DMSO-D ): δ 163.6, 161.2, 150.5, 147.5, 135.1, 132.2, 129.5, 25 A. A. Joshi and C. L. Viswanathan, Bioorg. Med. Chem. Lett.,
1
29.3, 127.9, 126.3, 125.5, 125.4, 124.4, 121.2, 117.9, 90.2, 30.6.
2006, 16, 2613–2617.
: C, 62.68; H, 3.71; N, 12.90%; Found: C, 26 Y.-L. Chen, K.-C. Fang, J.-Y. Sheu, S.-L. Hsu and C.-C. Tzeng, J.
Med. Chem., 2001, 44, 2374–2377.
3 2
Anal. Calcd. for C17H12ClN O
6
5
3
3
2.47; H, 3.76; N, 13.11%.
-(4-chlorophenyl)-5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H,
H)-dione (4x): Yield: 93%; Melting point: 194-196 C; IR (KBr): ν
342, 3024, 1699, 1621, 1394, 1124, 779, 554 cm ; H-NMR (400 28 Y. T. Tao, C. H. Chuen, C. W. Ko and J. W. Peng, Chem. Mater.,
27 Z. He, G. H. W. Milburn, A. Danel, A. Puchala, P. Tomasik and D.
o
Rasala, J. Mater. Chem., 1997, 7, 2323–2325.
–1 1
MHz, DMSO-D
6
): δ 11.26 (s, 1H), 10.10 (bs, 2H), 7.32-7.25 (m, 3H),
2002, 14, 4256–4261.
1
3
7.17 (d, 2H, J = 8.4Hz), 7.08-6.99 (m, 3H), 5.88 (s, 1H); C-NMR (100 29 C. H. Chuen and Y. T. Tao, Appl. Phys. Lett., 2002, 81, 4499–
MHz, DMSO-D
6
): δ 164.1, 161.6, 150.5, 143.6, 135.7, 130.2, 129.5,
4501.
128.9, 128.5, 128.0, 127.2, 125.1, 120.8, 90.4, 30.3. Anal. Calcd. for 30 C. W. Ko and Y. T. Tao, Appl. Phys. Lett., 2001, 79, 4234–4236.
C
17
H
12ClN
3
O
2
: C, 62.68; H, 3.71; N, 12.90%; Found: C, 62.81; H, 3.69; 31 Y. Chen, S. Wu, S. Tu, F. Shi and C. Li, J. Heterocycl. Chem.,
2008, 45, 1243–1246.
N, 12.76%.
3
2
D.-Q. Shi, L.-H. Niu, H. Yao and H. Jiang, J. Heterocycl. Chem.,
009, 46, 237–242.
2
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