1246
L. Wang et al.
PAPER
Anal. Calcd for C14H9N3O3: C, 62.92; H, 3.39; N, 15.72. Found: C,
62.86; H, 3.28; N, 15.61.
References
(1) Widdege, A. J. Prakt. Chem. 1887, 36, 141.
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W. L. F. Adv. Heterocycl. Chem. 1979, 24, 1. (c) Wolfe, J.
F.; Rathman, T. L.; Sleevi, M. C.; Campbell, J. A.;
Greenwood, T. D. J. Med. Chem. 1990, 33, 161.
3-(4-Nitrophenyl)quinazolin-4(3H)-one (4o)
Mp 165–166 °C.
IR (KBr): 1712, 1621, 1478 cm–1.
1H NMR (CDCl3): = 8.41 (d, J = 7.6 Hz, 1 H), 8.16 (s, 1 H), 7.71–
7.75 (m, 2 H), 7.51 (t, J = 7.4 Hz, 1 H), 7.90 (d, J = 8.63 Hz, 2 H),
8.0 (d, J = 8.7 Hz, 2 H).
13C NMR (CDCl3): = 165.28, 152.85, 147.84, 144.84, 144.10,
133.34, 127.15, 122.16, 121.34, 123.81.
(d) Gravier, D.; Dupin, J. P.; Casadebaig, F.; Hou, G.;
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GC/MS: m/z (%) = 267.0 (M+, 100), 268 (M+ + 1, 15).
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Anal. Calcd for C14H9N3O3: C, 62.92; H, 3.39; N, 15.72. Found: C,
62.85; H, 3.31; N, 15.63.
3-(2,4-Dinitrophenyl)quinazolin-4(3H)-one (4p)
Mp 150–152 °C.
IR (KBr): 1715, 1625, 1478 cm–1.
1H NMR (CDCl3): = 9.10 (s, 1 H), 8.17–8.56 (m, 4 H), 7.73–7.76
(m, 2 H), 7.51 (t, J = 7.4 Hz, 1 H).
13C NMR (CDCl3): = 167.21, 152.83, 147.86, 144.84, 144.0,
138.23, 133.3, 128.75, 127.15, 123.83, 122.16, 121.34, 120.43.
Anal. Calcd for C14H8N4O5: C, 53.85; H, 2.58; N, 17.94. Found: C,
68.76; H, 4.61; N, 15.01.
N-{4-[4-Oxo-3(4H)-quinazolinyl]phenyl}acetamide (4q)
Mp 198–200 °C.
IR (KBr): 1720, 1686, 1601, 1462 cm–1.
1H NMR (CDCl3): = 8.34 (d, J = 7.5 Hz, 1 H), 8.12 (s, 1 H), 8.02
(s, 1 H), 7.69–7.72 (m, 2 H), 7.47 (t, J = 7.4 Hz, 1 H), 7.36 (d,
J = 0.7 Hz, 2 H), 7.26 (d, J = 8.6 Hz, 2 H), 2.30 (s, 3 H).
13C NMR (CDCl3): = 168.25, 161.24, 147.84, 146.74, 136.55,
135.36, 134.65, 132.72, 131.54, 128.36, 127.31, 126.80, 125.15,
122.44, 19.05.
Anal. Calcd for C16H13N3O2: C, 68.81; H, 4.69; N, 15.05. Found: C,
68.76; H, 4.61; N, 15.01.
(6) Rosowsky, A.; Mota, C. E.; Wright, J. E.; Queener, S. F. J.
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3-Benzylquinazolin-4(3H)-one (4r)
Mp 118–120 °C.
IR (KBr): 1670, 1600, 1466 cm–1.
1H NMR (CDCl3): = 8.33 (d, J = 7.8 Hz, 1 H), 8.15 (s, 1 H), 7.70–
7.76 (m, 2 H), 7.49 (t, J = 7.2 Hz, 1 H), 7.27–7.35 (m, 5 H), 5.20 (s,
2 H).
13C NMR (CDCl3): = 160.94, 147.55, 146.58, 135.63, 134.52,
129.15, 128.91, 128.45 128.18, 127.66, 127.27, 127.12, 122.15,
49.75.
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GC/MS: m/z (%) = 236.1 (M+, 100), 235.1 (M – 1, 31), 237.1 (M +
1, 11).
Anal. Calcd for C15H12N2O: C, 76.25; H, 5.12; N, 11.86. Found: C,
76.15; H, 5.02; N, 11.76.
Acknowledgment
We thank the National Nature Science Foundation of China and the
Science Foundation of East China University of Science and Tech-
nology for their financial support.
Synthesis 2003, No. 8, 1241–1247 ISSN 1234-567-89 © Thieme Stuttgart · New York