A. Shaabani et al. / Tetrahedron Letters 44 (2003) 857–859
859
References
NMR spectral data and their mp’s compared with
literature reports.
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5-Methoxycarbonyl-6-methyl-4-(2-chlorophenyl)-3,4-
dihydropyrimidin-2(1H)-one, 15. Mp 252–254°C; IR
2. (a) Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M.
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(KBr) (wmax, cm−1): 3210, 3090, 1683, 1639; H NMR
1
(DMSO-d6): lH 2.28 (3H, s, CH3), 3.44 (3H, s, OCH3),
5.60 (1H, s, CH), 7.26–7.39 (4H, m, arom.), 7.70 (1H, s,
NH), 9.31 (1H, s, NH); 13C NMR: lC 18.2, 51.2, 51.9,
98.2, 128.2, 129.1, 129.9, 132.1, 141.9, 149.9, 151.9,
166.0; MS (m/z,%) 281 (M+, 29), 265 (M+−CH3, 62),
221 (M+−CH3CO2H, 27), 169 (100).
5-Methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-3,4-
dihydropyrimidin-2(1H)-one, 16. Mp 279–281°C; IR
(KBr) (wmax, cm−1): 3340, 3200, 3088, 1690, 1631; H
1
NMR (DMSO-d6): lH 2.27 (3H, s, CH3), 3.53 (3H, s,
OCH3), 5.29 (1H, s, CH), 7.61–8.12 (4H, m, arom.),
7.90 (1H, s, NH), 9.37 (1H, s, NH); 13C NMR: lC 18.4,
51.4, 53.8, 98.6, 121.4, 122.8, 130.7, 133.4, 147.2, 148.3,
150.1, 152.3, 166.1; MS (m/z,%) 292 (M++H, 25), 232
(M+−CH3CO2, 92),169 (100).
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5-Benzyloxycarbonyl-6-methyl-4-(phenyl)-3,4-dihy-
dropyrimidin-2(1H)-one, 23. Mp 165–167°C; IR (KBr)
1
(wmax, cm−1): 3345, 3218, 3100, 1703, 1637; H NMR
(DMSO-d6): lH 2.26 (3H, s, CH3), 5.00 and 5.04 (2H,
13. Yadav, J. S.; Reddy, B. V. S.; Reddy, E. J.; Ramalingam,
3
3
AB-system, J 12.7 Hz, OCH2), 5.16 (1H, d, J 2.9 Hz,
CH), 7.13–7.30 (10H, m, arom.), 7.72 (1H, s, NH), 9.23
(1H, s, NH), 13C NMR: lC 18.3, 54.4, 65.3, 99.2, 126.7,
127.8, 128.0, 128.2, 128.7, 128.9, 137.0, 145.1, 149.7,
152.4, 165.5; MS (m/z,%) 322 (M+, 45), 231 (M+−
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5-Benzyloxycarbonyl-6-methyl-4-(4-methoxyphenyl)-
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(KBr) (wmax, cm−1): 3340, 3210, 3100, 1695, 1630, 1603;
1H NMR (DMSO-d6): lH 2.25 (3H, s, CH3), 3.71 (3H,
3
s, OCH3), 4.99 and 5.04 (2H, AB system, J 12.7 Hz,
OCH2), 5.12 (1H, s, CH), 6.83–7.27 (9H, m, arom.),
7.68 (1H, s, NH), 9.21 (1H, s, NH), 13C NMR: lC 18.3,
53.8, 55.5, 65.2, 99.5, 114.2, 127.9, 128.0, 128.2, 128.7,
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Acknowledgements
Financial support by the Research Council of Shahid
Beheshti University is acknowledged.
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Soc. 1932, 54, 3751.