HETEROCYCLES, Vol. 83, No. 2, 2011
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2-Ethyl-2-methyl-2,3-dihydro-10-methylcarbonyl-4(1H)-azuleno[2,1-d]pyrimidinone (3f): Yellow
needles (from benzene). mp 201-202 ºC; (KBr, cm-1): ν 3286(NH), 3175(NH), 1657(C=O), 1642(C=O).
1H-NMR (CDCl3): δ 1.05 (3H, t, J = 7.2 Hz, CH3), 1.63 (3H, s, CH3), 1.89 (2H, q, J = 7.2 Hz, CH2), 3.98
(3H, s, COOCH3), 5.51 (1H, s, NH), 7.29 (1H, s, NH), 7.46 (1H, dd, J = 9.2, 9.6 Hz), 7.50 (1H, dd, J =
9.6, 10.0 Hz), 7.53 (1H, dd, J = 9.6, 10.0 Hz), 8.96 (1H, d, J = 10.0 Hz), 9.23 (1H, d, J = 10.0 Hz). Anal.
Calcd for C17H18N2O3: C 68.44, H 6.08, N 9.39. Found C 68.33, H 6.13, N 9.24.
2-Isopropyl-2-methyl-2,3-dihydro-10-methylcarbonyl-4(1H)-azuleno[2,1-d]pyrimi dinone (3g):
Yellow needles (from benzene). mp 194-196 ºC; (KBr, cm-1): ν 3296(NH), 3215(NH), 1659(C=O),
1
1632(C=O). H-NMR(CDCl3): δ 0.99 (6H, d, 2xCH3), 1.64 (3H, s, CH3), 1.77 (2H, d, J = 6.0 Hz, CH2),
1.98 (1H, m, CH), 3.98 (3H, s, COOCH3), 5.36 (1H, s, NH), 7.31 (1H, s, NH), 7.45 (1H, dd, J = 9.6, 10.0
Hz), 7.50 (1H, dd, J = 9.2, 10.0 Hz), 7.55 (1H, dd, J = 9.2, 9.6 Hz), 8.96 (1H, d, J = 10.0 Hz), 9.24 (1H, d,
J = 10.0 Hz). Anal. Calcd for C18H20N2O3: C 69.21, H 6.45, N 8.97. Found C 69.34, H 6.32, N 8.86.
2-Methyl-2-phenyl-2,3-dihydro-10-methylcarbonyl-4(1H)-azuleno[2,1-d]pyrimidi none (3h): Pale
yellow prisms (from benzene). mp 206-208 ºC; (KBr, cm-1): ν 3288(NH), 3224(NH), 1657(C=O),
1626(C=O). 1H-NMR (CDCl3): δ 2.01 (3H, s, CH3), 3.98 (3H, s, COOCH3), 6.08 (1H, s, NH), 7.28-7.30
(1H, m), 7.33-7.37 (2H, m), 7.50-7.54 (3H, m), 7.50 (1H,dd, J = 9.6, 9.6 Hz), 7.56-7.58 (2H, m), 7.78
(1H, s, NH), 9.02 (1H, d, J = 10.0 Hz), 9.24 (1H, d, J = 10.0 Hz). Anal. Calcd for C21H18N2O3: C 72.82, H
5.24, N 8.09. Found C 72.76, H 5.37, N 8.13.
2,2-Tetramethylene-2,3-dihydro-10-methylcarbonyl-4(1H)-azuleno[2,1-d]pyrimidi none (3i): Yellow
needles (from benzene). mp 192-193 ºC; (KBr, cm-1): ν 3265(NH), 3231(NH), 1663(C=O), 1631(C=O).
1H-NMR(CDCl3): δ 1.84-1.88 (4H, m), 2.04-2.08 (4H, m), 3.96 (3H, s, COOCH3), 6.02 (1H, s, brs), 7.42
(1H, s, NH), 7.46 (1H, dd, J = 9.2, 9.6 Hz), 7.51 (1H, dd, J = 9.6, 9.6 Hz), 7.53 (1H, dd, J = 9.6, 10.0 Hz),
8.95 (1H, d, J = 9.6Hz), 9.24 (1H, d, J = 10.0 Hz). Anal. Calcd for C18H18N2O3: C 69.66, H 5.85, N 9.03.
Found C 69.75, H 5.73, N 9.14.
2,2-Pentamethylene-2,3-dihydro-10-methylcarbonyl-4(1H)-azuleno[2,1-d]pyrimidi none (3j): Yellow
needles (from benzene). mp 226-227 ºC; (KBr, cm-1): ν 3282(NH), 3231(NH), 1654(C=O), 1631(C=O).
1H-NMR(CDCl3): δ 1.43-1.48 (2H, m), 1.66-1.68 (4H, m), 1.86-1.90 (2H, m), 1.95-1.99 (2H, m), 3.96
(3H, s, COOCH3), 6.15 (1H, s, NH), 7.29 (1H, s, NH), 7.44 (1H, dd, J = 9.6, 9.6 Hz), 7.49 (1H, dd, J =
9.6, 10.0 Hz), 7.51 (1H, dd, J = 9.6, 9.6 Hz), 7.62 (1H, s, NH), 8.96 (1H, d, J = 9.6 Hz), 9.22 (1H, d, J =
10.0 Hz). Anal. Calcd for C19H20N2O3: C 70.35, H 6.21, N 8.64. Found C 70.42, H 6.35, N 8.53.
We thank the Foundation of Innovation Team Project of Liaoning Education Department (No. 2008T001)
for financial support.