Synthesis of new pyrimidine, quinazoline and diazatricyclo derivatives by multicomponent reaction and evaluation of their biological activity

Article abstract of DOI:10.1080/10426507.2011.645175

A series of new pyrimidine and quinazoline derivatives was synthesized by a Biginelli-like reaction of urea/thiourea, aldehyde, and ketone in the presence of hydrochloric acid as a catalyst. In a similar way, some novel diazatricyclo derivatives were obtained via a Biginelli-like reaction followed by an intramolecular Michael-type addition. The yields of products were reasonable after recrystallization from ethanol. All newly synthesized compounds were characterized using IR and NMR (¹H and ¹³C) spectroscopy and elemental analysis. The antibacterial activity of these compounds was investigated against Staphylococcus aureus (RTCC, 1885), and Escherichia Coli (ATCC, 35922). Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright

Full text of DOI:10.1080/10426507.2011.645175

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Synthesis of New Pyrimidine,
Quinazoline and Diazatricyclo
Derivatives by Multicomponent Reaction
and Evaluation of Their Biological
Activity
Akbar Mobinikhaledi a , Naser Foroughifar a , Tahere Mosleh a
Ahmad Hamta b
a Department of Chemistry , Arak University , Arak , Iran
b Department of Biology , Arak University , Arak , Iran
&
Accepted author version posted online: 04 Jan 2012.Published
online: 05 Apr 2012.
To cite this article: Akbar Mobinikhaledi , Naser Foroughifar , Tahere Mosleh & Ahmad Hamta (2012)
Synthesis of New Pyrimidine, Quinazoline and Diazatricyclo Derivatives by Multicomponent Reaction
and Evaluation of Their Biological Activity, Phosphorus, Sulfur, and Silicon and the Related Elements,
187:6, 728-734, DOI: 10.1080/10426507.2011.645175
To link to this article: http://dx.doi.org/10.1080/10426507.2011.645175
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Phosphorus, Sulfur, and Silicon, 187:728–734, 2012
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2011.645175
SYNTHESIS OF NEW PYRIMIDINE, QUINAZOLINE AND
DIAZATRICYCLO DERIVATIVES BY MULTICOMPONENT
REACTION AND EVALUATION OF THEIR BIOLOGICAL
ACTIVITY
Akbar Mobinikhaledi,1 Naser Foroughifar,1 Tahere Mosleh,1
and Ahmad Hamta2
1Department of Chemistry, Arak University, Arak, Iran
2Department of Biology, Arak University, Arak, Iran
GRAPHICAL ABSTRACT
Abstract A series of new pyrimidine and quinazoline derivatives was synthesized by a
Biginelli-like reaction of urea/thiourea, aldehyde, and ketone in the presence of hydrochlo-
ric acid as a catalyst. In a similar way, some novel diazatricyclo derivatives were obtained via
a Biginelli-like reaction followed by an intramolecular Michael-type addition. The yields of
products were reasonable after recrystallization from ethanol. All newly synthesized compounds
were characterized using IR and NMR (1H and 13C) spectroscopy and elemental analysis. The
antibacterial activity of these compounds was investigated against Staphylococcus aureus
(RTCC, 1885), and Escherichia Coli (ATCC, 35922).
Supplemental materials are available for this article. Go to the publisher’s online edition of
Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
Keywords Multicomponent reaction; biginelli; michael addition; pyrimidine; quinazoline
INTRODUCTION
Multicomponent reactions (MCRs) are one-step processes in which three or more
reactants are reacted together to produce a new product without the isolation of the in-
termediates, where all or most of the atoms contribute to the structure of new product.
These reactions are used as valuable tools for rapid and efficient synthesis of organic and
Received 19 October 2011; accepted 23 November 2011.
We thank the Department of Chemistry of Arak University for providing financial support.
Address correspondence to Akbar Mobinikhaledi, Department of Chemistry, Arak University, Arak 38156-
879, Iran. E-mail: akbar mobini@yahoo.com
728

SYNTHESIS OF NEW PYRIMIDINE, QUINAZOLINE AND DIAZATRICYCLO DERIVATIVES 729
Table 1 Synthesis of pyrimidine and quinazolinone derivatives 4a–g
Entry
Ketone
X
Product 4
Time (h)
Yield (%)
1
2
3
4
5
6
7
acetone
cyclohexanone
cyclohexane-1,4-dione
1,4-cyclohexadione
2-bromoacetophenone
acetone
O
S
O
S
O
S
S
a
b
c
d
e
f
7
3
6
4
5
6
7
54
73
68
71
62
65
70
acetophenone
g
drug-like compounds containing biological screening due to several aspects including min-
imum preparative work setup and high degree of diversity.1
The original Biginelli reaction, the synthesis of dihydropyrimidinones, is one of the
most useful examples of MCRs, has received considerable attentions in organic synthesis
and medicinal chemistry due to their capacity to produce multifunctionalized products
including tetrahydropyrimidines, their thiones analogs, and other related heterocyclic com-
pounds.2 This reaction has developed based on the number of starting materials and in
order to obtain derivatives with different structures and biological activities.3 Dihydropy-
rimidine,4 quinazoline,5,6 and diazatricyclo derivatives7 have aroused considerable interest
because of their pharmacological and therapeutic properties such as antibacterial, antitumor,
and antihypertensive activities as well as behaving as calcium channel blockers.8–19
In view of these reports and also as a continuation of our work on the synthesis
of pyrimidine derivatives and MCRs,20–26 we have made an attempt to synthesize some
biologically active, novel pyrimidine, quinazolinone and diazatricyclo derivatives via a
Biginelli-like reaction and an intramolecular Michael-type addition reaction.
RESULTS AND DISCUSSION
The synthetic routes for the preparation of titled compounds are presented in
Scheme 1. The good yields of the products, the mild reaction conditions, and the use
of simple starting materials are the main advantages of this method. Pyrimidines and quina-
zolinones 4a–g, and diazatricyclos 5a–g were synthesized by a Biginelli-like reaction of
benzaldehyde or salicylaldehyde with urea/thiourea and appropriate ketone in the presence
of hydrochloric acid as a catalyst. The results are indicated in Tables 1 and 2.
Scheme 1
When salicylaldehyde was used as a starting material, due to existence of an OH
group at the ortho position, a bridge oxygen is created with C-6 of the pyrimidine ring.

730
A. MOBINIKHALEDI ET AL.
Table 2 Synthesis of diazatricyclo derivatives 5a–g
Entry
Ketone
X
Product 5
Time (h)
Yield (%)
1
2
3
4
5
6
7
acetone
acetone
cyclohexanone
cyclohexanone
acetophenone
O
S
O
S
O
S
O
a
b
c
d
e
f
4
2
3
2
3
4
5
80
76
65
70
73
68
64
acetophenone
4ꢁ-bromoacetophenone
g
Steric effects appear to influence the formation of this product. The formation of the oxygen
bridge may be due to the effective distance between the ortho-hydroxyl group of phenol and
the C-6 atom of pyrimidine ring.27,28 So, the formation of the oxygen bridge via a Michael
addition reaction resulted in the synthesis of diazatricyclo compounds 5a–g is observed in
Biginelli-like reaction when salicylaldehyde is used as a starting material.
The NMR spectra and IR spectra data of all synthesized compounds are consistent
with the expected structures. The appearance of two singlets at ∼6.60–9.70 ppm in the 1H
NMR spectrum of 4a–g and 5a–g due to the resonance of two NH groups (disappeared
on D2O addition) and also the appearance of the absorption bond at ∼3184–3421 cm−1 in
the IR spectra of these compounds, the characteristic of the NH group, are good evidences
in support of expected reactions. In 13C NMR spectra of compounds, the appearance of
signals at lowest field is due to resonance of C O and C S groups. The other chemical
shift of 13C NMR spectra was papered in expected regions.
The verification of antibacterial screening data revealed that 4 out of 15 tested ma-
terials showed antibacterial activities against Stphylococcus aureus as gram positive and
three of these materials showed antibacterial activities against Escherichia Coli as gram
negative bacteria (Table S31 Supplemental Materials). The maximum activities against
Staphylococcus aureus and Escherichia Coli were related to 4c and 4g, respectively.
CONCLUSION
We have been able to synthesize some novel and biological active pyrimidine, quina-
zolinone, and diazatricyclo derivatives via the Biginelli-like and an intramolecular Michael-
type addition reaction of urea/thiourea, aldehyde, and ketone in suitable yields.
EXPERIMENTAL
All reagents and solvents used were commercially available. Melting points were
measured using an electro-thermal digital apparatus. IR spectra were performed on a
Galaxy series FTIR 5000 spectrometer using KBr discs. The NMR spectra were recorded
on a Bruker Avance 300 MHz spectrometer using Dimethylsulfoxide (DMSO-d6) as a
solvent and TMS as an internal standard. Microanalyses were performed by the Elemental
Analyzer (Elemental, Vario EL III) at the Arak University. Reactions were monitored by
thin layer chromatography using silica gel F254 aluminum sheets (Merck). The microbial
strains are identified strains and were obtained from the Pasteure Institute of Iran. The

SYNTHESIS OF NEW PYRIMIDINE, QUINAZOLINE AND DIAZATRICYCLO DERIVATIVES 731
bacterial strains studied are Staphylococcus aureus (RTCC, 1885) and Escherichia Coli
(ATCC, 35922).
Antibacterial Study
The agar disk diffusion method was used for this purpose. The chemically synthesized
material (5 mg) was dissolved in DMSO (200 µl) as a solvent and 100 µl of known
concentration of the test compounds was introduced onto the disks (7 mm). The disk was
saturated with the test compound. Then, the disk was introduced onto the upper layer of the
medium with the bacteria. Then, 100 µl of solvent (DMSO) was added to blank disk and
implanted as negative control on each plate along with the standard drugs. The plates were
incubated overnight at 37◦C. The inhibition zones were measured and compared with the
controls. Chloramphenicol was used as a standard drug.
General Experimental Procedure for Synthesis of 4 and 5
An equimolar amount of benzaldehyde or salicylaldehyde 1, urea or thiourea 2,
ketone 3, and a few drops of hydrochloric acid (37%) in ethanol (20 mL) was refluxed
for an appropriate time as indicated in Tables 1a and 2. After completion of reaction,
monitored by TLC, the reaction mixture was cooled to room temperature, filtered, washed
by hot water and, ethanol and recrystallized from ethanol to afford the pure product of 4
and 5. Supplemental Materials shows the 1H and 13C NMR spectra for two representative
compounds, 4e and 5e.
6-Methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one (4a). Mp 305–307 ◦C. IR
(KBr), ν (cm−1): 3300 (NH), 3223 (NH), 3068 (CHaromatic), 2972 (CHaliphatic), 1658
(C O). 1H NMR (DMSO-d6, 300 MHz), δ (ppm) 1.68 (s, 3H, CH3), 4.91 (d, J = .0 Hz,
1H, Hpyrimidine), 5.06 (d, J = 9.0 Hz, 1H, CH), 6.60 (s, 1H, NH), 6.81 (s, 1H, NH), the NH
protons disappeared on D2O addition, 7.06–7.44 (m, 5H, Haromatic). 13C NMR (DMSO-d6,
75 MHz), δ (ppm) 43.8, 49.9, 126.7, 127.7, 127.9, 128.8, 142.1, 143.2, 156.1. Anal cald
for: C11H12N2O, C, 70.19; H, 6.43; N, 14.88%. Found: C, 70.29; H, 6.50; N, 14.64%.
4-Phenyl-3,4,5,6,7,8-hexahydroquinazoline-2(1H)-thione (4b). Mp 309–311 ◦C. IR
1
(KBr), ν (cm−1): 3396 (NH), 3184 (NH), 3082 (CHaromatic), 2957 (CHaliphatic). H NMR
(DMSO-d6, 300 MHz), δ (ppm) 1.03 (m, 2H, CH2), 1.08 (m, 2H, CH2), 1.53 (m, 2H, CH2),
1.60 (m, 2H, CH2), 4.52 (s, 1H, Hpyrimidine), 7.23–7.43 (m, 5H, Haromatic), 8.61 (s, 1H, NH),
8.92 (s, 1H, NH), the NH protons disappeared on D2O addition. 13C NMR (DMSO-d6, 75
MHz), δ (ppm) 18.6, 39.1, 56.6, 57.1, 68.1, 126.4, 127.4, 128.1, 128.5, 129.0, 129.3, 175.4.
Anal cald for: C14H16N2S, C, 68.81; H, 6.60; N, 11.46; S, 13.12%. Found: C, 68.73; H,
6.51; N, 11.54; S, 13.24%.
◦
4-Phenyl-3,4,7,8-tetrahydroquinazoline-2,6(1H,5H)-dione (4c). Mp 340–341 C.
IR (KBr), ν (cm−1): 3394 (NH), 3223 (NH), 3082 (CHaromatic), 2910 (CHaliphatic), 1678
(C O), 1669 (C O). 1H NMR (DMSO-d6, 300 MHz), δ (ppm) 2.12–2.59 (m, 6H, 3CH2),
4.67 (s, 1H, Hpyrimidine), 7.04–7.60 (m, 5H, Haromatic), 8.09 (s, 1H, NH), 9.07 (s, 1H, NH).),
the NH protons disappeared on D2O addition. 13C NMR (DMSO-d6, 75 MHz), δ (ppm)
24.4, 27.3, 54.7, 58.9, 127.2, 128.1, 129.0, 129.3, 143.3, 144.3, 152.6, 152.9. Anal cald for:
C14H14N2O2, C, 69.41; H, 5.82; N, 11.56%. Found: C, 69.29; H, 5.60; N, 11.66%.
4-Phenyl-2-thioxo-1,2,3,4,7,8-hexahydroquinazolin-6(5H)-one (4d). Mp 325–
327 ◦C. IR (KBr), ν (cm−1): 3375 (NH), 3210 (NH), 3088 (CHaromatic), 2978 (CHaliphatic),
1689 (C O). 1H NMR (DMSO-d6, 300 MHz), δ (ppm) 2.24 (s, 2H, CH2), 2.60–2.70 (m,

732
A. MOBINIKHALEDI ET AL.
4H, 2CH2,), 4.76 (s, 1H, Hpyrimidine), 7.11–7.43 (m, 5H, Haromatic), 8.76 (s, 1H, NH), 9.58 (s,
1H, NH)), the NH protons disappeared on D2O addition. 13C NMR (DMSO-d6, 75 MHz),
δ (ppm) 23.6, 26.8, 54.2, 58.2, 125.2, 127.4, 128.4, 128.7, 129.1, 142.8, 142.9, 173.2. Anal
cald for: C14H14N2OS, C, 65.09; H, 5.46; N, 10.84; S, 12.41%. Found: C, 65.19; H, 5.40;
N, 10.97; S, 12.65%.
5-Bromo-6-hydroxy-4,6-diphenyl-tetrahydropyrimidin-2(1H)-one (4e). Mp 220–
222 ◦C. IR (KBr), ν (cm−1): 3217 (NH), 3190 (NH, OH), 3080 (CHaromatic), 2980
(CHaliphatic), 1682 (C O). 1H NMR (DMSO-d6, 300 MHz), δ (ppm) 3.68 (d, J = 5.6 Hz,
1H, Hpyrimidine), 5.05 (d, J = 5.6 Hz, 1H, CHBr), 7.27–7.51 (m, 11H, 10Haromatic, 1H, OH),
8.15 (s, 1H, NH), 8.81 (s, 1H, NH), the NH and OH protons disappeared on D2O addition.
13C NMR (DMSO-d6, 75 MHz), δ (ppm) 20.4, 55.5, 66.4, 123.8, 127.2, 128.0, 128.4, 128.9,
132.2, 132.8, 144.1, 153.5. Anal cald for: C16H15BrN2O2, C, 55.35; H, 4.35; N, 8.07; Br,
23.01%. Found: C, 55.18; H, 4.50; N, 8.19; Br, 23.26%.
6-Hydroxy-6-methyl-4-phenyl-tetrahydropyrimidine-2(1H)-thione (4f). Mp 238–
240 ◦C. IR (KBr), ν (cm−1): 3387 (NH), 3196 (NH, OH), 3082 (CHaromatic), 2974
1
(CHaliphatic). H NMR (DMSO-d6, 300 MHz), δ (ppm) 0.91 (s, 3H, CH3), 2.75 (t, J =
5.6 Hz, 1H, Hpyrimidine), 4.05 (d, J = 5.6 Hz, 2H, CH2), 7.21–7.41 (m, 6H, 5Haromatic and
1H, OH), 8.19 (s, 1H, NH), 8.81 (s, 1H, NH), the NH and OH protons disappeared on D2O
addition. 13C NMR (DMSO-d6, 75 MHz), δ (ppm) 29.1, 43.0, 54.9, 65.0, 127.2, 128.4,
129.1, 140.3, 174.7. Anal cald for: C11H14N2OS, C, 59.43; H, 6.35; N, 12.60; S, 14.42%.
Found: C, 59.21; H, 6.44; N, 12.49; S, 14.52%.
6-Hydroxy-4,6-diphenyl-tetrahydropyrimidine-2(1H)-thione (4g). Mp 285–287 ◦C.
IR (KBr), ν (cm−1): 3387 (NH), 3210 (NH, OH), 3063 (CHaromatic), 2949 (CHaliphatic).1H
NMR (DMSO-d6, 300 MHz), δ (ppm) 3.15 (d, J = 5.6 Hz, 2H, CH2), 4.14 (t, J = 5.6 Hz,
1H, Hpyrimidine), 6.97–6.99 (m, 5H, Haromatic), 7.13–7.15 (m, 6H, 5H, Haromatic, 1H, OH), 8.18
(1H, NH), 8.98 (1H, NH), the NH and OH protons disappeared on D2O addition. 13C NMR
(DMSO-d6, 75 MHz), δ (ppm) 44.7, 55.4, 69.2, 126.9, 127.1, 127.8, 128.0, 128.4, 128.6,
139.4, 140.3, 175.8. Anal cald for: C16H16N2OS, C, 67.58; H, 5.67; N, 9.85; S, 11.28%.
Found: C, 67.81; H, 5.50; N, 9.98; S, 11.03%.
9-Methyl-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-triene-11-one (5a). Mp
291–293 ◦C. IR (KBr), ν (cm−1): 3310 (NH), 3240 (NH), 3122 (CHaromatic), 2891
1
(CHaliphatic), 1687 (C O). H NMR (DMSO-d6, 300 MHz), δ (ppm) 1.59 (s, 3H, CH3),
2.08 (d, J = 5.6 Hz, 2H, CH2), 4.23 (t, J = 5.6 Hz, 1H, Hpyrimidine), 6.73-7.13 (m, 4H,
Haromatic), 7.29 (s, 1H, NH), 7.59 (s, 1H, NH), the NH protons disappeared on D2O addition
13C NMR (DMSO-d6, 75 MHz), δ (ppm) 26.8, 32.6, 44.9, 82.6, 116.9, 120.5, 126.1, 129.3,
129.4, 151.8, 155.7. Anal cald for: C11H12N2O2, C, 64.69; H, 5.92; N, 13.72%. Found: C,
64.51; H, 5.99; N, 13.56%.
9-Methyl-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-triene-11-thione (5b).
◦
Mp 225–227 C. IR (KBr), ν (cm−1): 3210 (NH), 3194 (NH), 3099 (CHaromatic), 2968
1
(CHaliphatic). H NMR (DMSO-d6, 300 MHz), δ (ppm) 1.66 (s, 3H, CH3), 2.09 (d, J =
5.6 Hz, 2H, CH2), 4.30 (t, J = 5.6 Hz, 1H, Hpyrimidine), 6.78–7.18 (m, 4H, Haromatic), 8.80
(s, 1H, NH), 9.01 (s, 1H, NH), the NH protons disappeared on D2O addition. 13C NMR
(DMSO-d6, 75 MHz), δ (ppm) 25.9, 30.9, 45.5, 81.0, 116.8, 120.9, 124.3, 129.5, 129.7,
151.7, 176.5. Anal cald for: C11H12N2OS, C, 59.97; H, 5.49; N, 12.72; S, 14.56%. Found:
C, 59.81; H, 5.60; N, 12.53; S, 14.78%.
2-Oxa-15,17-diazatricyclo[7.5.3.01,10.03,8]heptadeca-3,5,7-triene-16-one (5c). Mp
314–316 ◦C. IR (KBr), ν (cm−1): 3300 (NH), 3230 (NH), 3080 (CHaromatic), 2943
1
(CHaliphatic), 1689 (C O). H NMR (DMSO-d6, 300 MHz), δ (ppm) 1.34–2.12 (m, 9H,

SYNTHESIS OF NEW PYRIMIDINE, QUINAZOLINE AND DIAZATRICYCLO DERIVATIVES 733
4CH2, 1H, CH), 3.90 (s, 1H, Hpyrimidine), 6.73–7.13 (m, 4H, Haromatic), 7.16 (s, 1H, NH),
7.31 (s, 1H, NH), the NH protons disappeared on D2O addition. 13C NMR (DMSO-d6, 75
MHz), δ (ppm) 22.8, 24.4, 25.3, 35.1, 36.2, 48.7, 85.0, 116.8, 120.4, 127.7, 129.2, 129.3,
151.4, 155.5. Anal cald for: C14H16N2O2, C, 68.83; H, 6.60; N, 11.47%. Found: C, 68.64;
H, 6.74; N, 11.31%.
2-Oxa-15,17-diazatricyclo[7.5.3.01,10.03,8] heptadeca-3,5,7-triene-16-thione (5d).
◦
Mp 225–227 C. IR (KBr), ν (cm−1): 3421 (NH), 3194 (NH), 3065 (CHaromatic), 2949
(CHaliphatic). 1H NMR (DMSO-d6, 300 MHz), δ (ppm) 1.02–2.49 (m, 9H, 4CH2, 1H, CH),
3.43 (s, 1H, Hpyrimidine), 7.11–7.22 (m, 4H, Haromatic), 8.64 (s, 1H, NH), 9.02 (s, 1H, NH),
the NH protons disappeared on D2O addition. 13C NMR (DMSO-d6, 75 MHz), δ (ppm)
19.0, 23.5, 24.4, 31.2, 49.4, 56.5, 83.7, 119.0, 121.6, 124.4, 126.4, 128.5, 154.4, 177.3.
Anal cald for: C14H16N2OS, C, 64.58; H, 6.19; N, 10.76; S, 12.32%. Found: C, 64.69; H,
6.01; N, 10.84; S, 12.05%.
9-Phenyl-8-oxa-10,12-diazatricyclo [7.3.1.02,7]trideca-2,4,6-triene-11-one (5e). Mp
271–273 ◦C. IR (KBr), ν (cm−1): 3323 (NH), 3219 (NH), 3070 (CHaromatic), 2982
1
(CHaliphatic), 1687 (C O). H NMR (DMSO-d6, 300 MHz), δ (ppm) 2.19 (d, J = 5.6
Hz, 2H, CH2), 4.33 (t, J = 5.6 Hz, 1H, Hpyrimidine), 6.81–7.88 (m, 9H, Haromatic), 8.64 (s, 1H,
NH), 9.70 (s, 1H, NH), the NH protons disappeared on D2O addition. 13C NMR (DMSO-d6,
75 MHz), δ (ppm) 35.3, 49.9, 85.2, 121.0, 125.6, 126.2, 126.9, 128.3, 128.7, 129.5, 131.3,
134.6, 151.7, 156.3. Anal cald for: C16H14N2O2, C, 72.16; H, 5.30; N, 10.52%. Found: C,
72.05; H, 5.21; N, 10.73%.
9-Phenyl-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-triene-11-thione (5f).
◦
Mp 265–267 C. IR (KBr), ν (cm−1): 3360 (NH), 3210 (NH), 3043 (CHaromatic), 2937
1
(CHaliphatic). H NMR (DMSO-d6, 300 MHz), δ (ppm) 2.49 (d, J = 5.6 Hz, 2H, CH2),
3.99 (t, J = 5.6 Hz, 1Hpyrimidine), 7.04–7.70 (m, 9H, Haromatic), 8.85 (s, 1H, NH), 9.62 (s,
1H, NH), the NH protons disappeared on D2O addition. 13C NMR (DMSO-d6, 75 MHz),
δ (ppm) 36.1, 48.4, 86.7, 122.1, 126.6, 129.1, 129.7, 130.1, 130.4, 132.5, 141.1, 151.5,
153.9, 175.9. Anal cald for: C16H14N2OS, C, 68.06; H, 5.00; N, 9.92; S, 11.36%. Found:
C, 68.21; H, 5.12; N, 9.71; S, 11.54%.
9-(4-Bromophenyl)-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-triene-11-
one (5g). Mp 285–287 ◦C. IR (KBr), ν (cm−1): 3317 (NH), 3221 (NH), 3074 (CHaromatic),
2912 (CHaliphatic), 1683 (C O). 1H NMR (DMSO-d6, 300 MHz), δ (ppm) 2.17 (d, J = 5.6
Hz, 2H, CH2), 4.32 (t, J = 5.6 Hz, 1Hpyrimidine), 6.93–7.26 (m, 4H, Haromatic), 7.41–7.62
(m, 4H, Haromatic), 7.65 (s, 1H, NH), 7.89 (s, 1H, NH), the NH protons disappeared on D2O
addition. 13C NMR (DMSO-d6, 75 MHz), δ (ppm) 35.1, 45.1, 84.9, 121.2, 122.1, 126.0,
128.7, 129.4, 129.6, 131.5, 131.7, 141.4, 151.4, 156.0. Anal cald for: C16H13BrN2O2, C,
55.67; H, 3.80; N, 8.12; Br, 23.15%. Found: C, 55.51; H, 3.71; N, 7.96; Br, 23.26%.
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