Molecules 2009, 14
1508
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ν(C=C)ar 1597, 1569, 1513, 1483; H-NMR (δ ppm): 2.41 (s, 3H, CH3-C’-3), 2.69 (s, 3H, CH3-C=N),
7.09-7.65 (ABq, 4H, phenyl, 3J=8.43 Hz 7.3 (m, 1H, C-6-H), 7.4 (dd, 1H, C-8-H, J8,7=8.3 Hz, J8,6=1.1
Hz), 7.6 (dd, 1H, C-5-H, J5,6=7.8 Hz, J5,7=1.7 Hz), 7.7 (m, 1H, C-7-H), 16.07 (bs, 1H, OH-C-4); MS:
m/z (%): 293 (M+, 91), 292 (100), 278 (32), 276 (20), 264 (5), 236 (2), 188 (21), 187 (12), 172 (9), 158
(5), 145 (5), 144 (12), 132 (10), 121 (23), 107 (12), 106 (11), 91 (23), 77 (8), 65 (16), 51 (3); Anal. for
C18H15NO3 (293.32) (%): C: 73.71, H: 5.15, N: 4.78: found C: 73.72, H: 5.12, N: 4.79.
4-Hydroxy-3-(1-(m-tolylimino)ethyl)-2H-chromen-2-one (11b): Yield 94%; m.p. 109-110 ºC. IR (KBr,
cm-1): ν(OH) 3417, ν(=CH)ar 3067, ν(CH3) 2982, 2929, 2853, ν(C=O) 1697 (lactone), ν(C=N) 1606 (imino),
ν(C=C)ar 1600, 1566, 1484; 1H-NMR (δ ppm): 2.42 (s, 3H, CH3-C’-3), 2.70 (s, 3H, CH3-C=N), 7.01 (dd,
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1H, C-4’-H, 3J4’,5’=7.58 Hz, J4’,6’=1.14 Hz,), 7.04 (dd, 1H, C-6’-H, J6’,5’ =8.12 Hz, 4J6’,4’=1.14 Hz),
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7.12 (s, 1H, C-2’-H), 7.25 (dd, 1H, J5’,4’=7.58 Hz, C-5’-H, J5’,6’=8.12 Hz), 7.3 (m, 1H, C-6-H), 7.4
(dd, 1H, C-8-H, 3J8,7=8.3 Hz, 4J8,6=1.1 Hz), 7.6 (dd, 1H, C-5-H, 3J5,6=7.8 Hz, 4J5,7=1.7 Hz), 7.7 (m, 1H,
C-7-H), 15.9 (bs, 1H, OH-C-4); MS: m/z (%): 293 (M+, 81), 292 (100), 278 (30), 276 (12), 264 (3),
236 (3), 188 (14), 187 (27), 172 (11), 158 (7), 145 (13), 144 (12), 132 (10), 121 (19), 107 (12), 106 (6),
91 (20), 77 (9), 65 (15), 51 (4); Anal. for C18H15NO3 (293.32) (%): C: 73.71, H: 5.15, N: 4.78; found
C: 73.72, H: 5.14, N: 4.79.
4-Hydroxy-3-(1-(o-tolylimino)ethyl)-2H-chromen-2-one (12b): Yield 94%; m.p. 138-139 ºC. IR (KBr,
cm-1): ν(OH) 3466.94, ν(=CH)ar 3072.51, ν(CH3) 2935.08, 2856.34, ν(C=O) 1711.85 (lactone), ν(C=N) 1610.82
(imino), ν(C=C)ar 1594.26, 1562.86, 1486.38; 1H-NMR (δ ppm): 2.30 (s, 3H, CH3-C-1’), 2.81 (CH3-
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C=N), 7.23 (dd, 1H, C-6’-H, J6’,5’=8.01 Hz, J6’,4’=1.12 Hz), 7.28 (dd, 1H, C-3’-H, J3’,4’=7.62 Hz,
4J3’,5’=1.11 Hz), 7.3 (m, 1H, C-6-H), 7.4 (dd, 1H, C-8-H, 3J8,7=8.3 Hz, 4J8,6=1.1 Hz), 7.37 (m, 1H, C-5’-
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H), 7.6 (dd, 1H, C-5-H, J5,6=7.8 Hz, J5,7=1.7 Hz), 7.7 (m, 1H, C-7-H), 15.8 (bs, 1H, OH-C-4); MS:
m/z (%): 293 (M+, 42), 292 (34), 278 (100), 188 (7), 187 (11), 172 (8), 158 (15), 145 (4), 144 (9), 132
(9), 121 (16), 107 (2), 106 (3), 91 (17), 77 (6), 65 (13), 51 (6); Anal. for C18H15NO3 (293.32) (%): C:
73.71, H: 5.15, N: 4.78: found C: 73.75, H: 5.21, N: 4.73.
4-Hydroxy-3-(1-(4-nitrophenylimino)ethyl)-2H-chromen-2-one (13b): Yield 92%; m.p. 212-215 ºC. IR
(KBr, cm-1): ν(OH) 3414, ν(=CH)ar 3081, 3046, ν(CH3) 2992, 2947, 2849, ν(C=O) 1707 (lactone), ν(C=N) 1608
(imino), ν(C=C)ar 1580, 1519, 1483, νar(NO2) 1557, 1340; 1H-NMR (δ ppm): 2.76 (s, 3H, CH3-C=N), 7.3
(m, 1H, C-6-H), 7.4 (dd, 1H, 8-H, J8,7=8.3 Hz, J8,6=1.1 Hz), 7.43 (d, 2H, 3J3’, 2’=3J5’,6’=8.9 Hz, 3’-H, C-
5’-H), 7.6 (dd, 1H, C-5-H, 3J5,6=7.8 Hz, 4J5,7=1.7 Hz), 7.7 (m, 1H, C-7-H), 8.39 (d, 2H, 3J2’,3’=J6",5"=8.9
Hz, C-2’-H, C-6’-H), 15.95 (bs, 1H, OH-C-4); MS: m/z (%): 324 (M+, 60), 323 (100), 309 (8), 307
(10), 294 (14), 277 (18), 263 (8), 221 (1), 207 (7), 203 (6), 188 (26), 187 (47), 176 (6), 163 (9), 157
(9), 121 (48), 117 (12), 108 (7), 92 (14), 77 (9), 76 (13), 67 (14), 65 (12); Anal. for C17H12N2O5
(324.29) (%): C: 62.96, H: 3.73, N: 8.64: found; C: 62.97, H: 3.77, N: 8.69.
4-Hydroxy-3-(1-(3-nitrophenylimino)ethyl)-2H-chromen-2-one (14b): Yield: 97%; m.p. 209-210 ºC.
IR (KBr,cm-1): ν(OH) 3416, ν(=CH)ar 3089, 3062, ν(CH3) 2980, 2936, 2853, ν(C=O) 1705 (lactone), ν(C=N)
1609 (imino), ν(C=C)ar 1590, 1538, 1491, νar(NO2) 1562, 1353; 1H-NMR (δ ppm): 2.61 (s, 3H, CH3-C=N),
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7.26 (dd, 1H, 6’-H, J6’,5’=8.02 Hz, J6’,4’=1.12 Hz), 7.3 (m, 1H, C-6-H), 7.34 (s, 1H, C-2’-H), 7.4 (dd,