HETEROCYCLES, Vol. 65, No. 12, 2005
2943
4H), 2.41 (s, 3H), 3.10 (br, 4H), 3.82 (s, 3H), 6.76 (d, J = 2.3 Hz, 1H), 6.81 (dd, J = 2.3, 8.7 Hz, 1H), 7.44
13
(d, J = 8.7 Hz, 1H); C-NMR (CDCl3) δ: 13.5, 26.0, 50.6, 55.7, 100.3, 112.0, 114.6, 125.9, 130.1, 147.3,
153.2, 159.0, 161.2; MS (C15H17NO3), m/z (% rel. int.): 259 (M+, 100), 231 (22), 190 (11), 174 (14), 162
(8); Anal. Calcd for C15H17NO3: C, 69.48; H, 6.61; N, 5.40. Found: C, 69.34; H, 6.51; N, 5.62.
4,7-Dimethyl-3-(N-thiomorpholino)coumarin (VIb3)
-1
1
O
Yield 9%, mp 152-154 C; IR (cm ): 1711 (C=O), 1615 (C=C); H-NMR (CDCl3) δ: 2.40 (s, 3H), 2.45 (s,
3H), 2.74 (br, 4H), 3.30 (br, 4H), 7.05 (br, 1H), 7.07 (s, 1H), 7.44 (d, J = 8.5 Hz, 1H); 13C-NMR (CDCl3) δ:
13.5, 21.5, 28.5, 52.3, 116.7, 118.3, 125.0, 125.3, 134.3, 141.5, 146.1, 151.8, 159.3; MS (C15H17NO2S), m/z
(% rel. int.): 275 (M+, 100), 215 (24), 189 (16), 174 (48), 145 (18), 115 (16); Anal. Calcd for C15H17NO2S:
C, 65.43; H, 6.22; N, 5.09; S, 11.64. Found: C, 65.42; H, 6.22; N, 4.77; S, 11.72.
4,7-Dimethyl-3-(N-pyrrolidino)coumarin (VIb4)
Yield 22%, mp 91-93 OC; IR (cm-1): 1724 (C=O), 1608 (C=C); 1H-NMR (CDCl3) δ: 1.93 (quint, J = 3.2 Hz,
4H), 2.38 (s, 3H), 2.41 (s, 3H), 3.14 (t, J = 6.4 Hz, 4H), 7.02 (br, 1H), 7.04 (s, 1H), 7.40 (d, J = 8.6 Hz, 1H);
13C-NMR (CDCl3) δ: 13.6, 21.4, 26.0, 50.9, 116.5, 118.6, 124.7, 125.2, 131.3, 140.8, 146.5, 151.6, 158.8;
MS (C15H17NO2), m/z (% rel. int.): 243 (M+, 100), 215 (55), 174 (37), 145 (13), 115 (15); Anal. Calcd for
C15H17NO2: C, 74.05; H, 7.04; N, 5.76. Found: C, 74.02; H, 7.06; N, 5.78.
7-Methoxy-4-(N-piperidinomethyl)coumarin (VIIa1)
-1
1
O
Yield 65%, mp 114-115 C; IR (cm ): 1724 (C=O), 1608 (C=C); H-NMR (CDCl3) δ: 1.43 (br, 2H), 1.57
(br, 4H), 2.43 (br, 4H), 3.51 (s, 2H), 3.84 (s, 3H), 6.34 (s, 1H), 6.78 (d, J = 2.4 Hz, 1H), 6.81 (dd, J = 2.4,
8.8 Hz, 1H), 7.74 (d, J = 8.8 Hz, 1H); 13C-NMR (CDCl3) δ: 24.0, 25.9, 54.9, 55.7, 59.9, 100.8, 111.8, 112.1,
112.7, 125.9, 151.8, 155.7, 161.4, 162.5; HRMS exact molar mass calculated for C16H19NO3 (M+) 273.1364,
found: 273.1397; Anal. Calcd for C16H19NO3: C, 70.31; H, 7.01; N, 5.12. Found: C, 70.34; H, 7.33; N, 5.29.
7-Methoxy-4-(N-morpholinomethyl)coumarin(VIIa2)
-1
1
O
Yield 80%, mp 129-131 C; IR (cm ): 1705 (C=O), 1615 (C=C); H-NMR (CDCl3) δ: 2.50 (t, J = 4.5 Hz,
4H), 3.55 (s, 2H), 3.68 (t, J = 4.5 Hz, 4H), 3.83 (s, 3H), 6.32 (s, 1H), 6.77 (d, J = 2.4 Hz, 1H), 6.80 (dd, J =
2.4, 8.8 Hz, 1H), 7.70 (d, J = 8.8 Hz, 1H); 13C-NMR (CDCl3) δ: 53.8, 55.7, 59.5, 66.9, 100.9, 112.0, 112.2,
112.4, 125.8, 151.5, 155.7, 161.2, 162.6; HRMS exact molar mass calculated for C15H17NO4 (M+) 275.1157,
found: 275.1179; Anal. Calcd for C15H17NO4: C, 65.44; H, 6.22; N, 5.09. Found: C, 65.21; H, 6.32; N, 5.21.
7-Methoxy-4-[2-(N-pyridyl)-N-benzylaminomethyl]coumarin (VIIa5)
Yield 25%, mp 127-128 OC; IR (cm-1): 1705 (C=O), 1615 (C=C); 1H-NMR (CDCl3) δ: 3.84 (s, 3H), 4.74 (s,
2H), 4.96 (d, J = 0.9 Hz, 2H), 6.08 (s, 1H), 6.79 (d, J = 2.5 Hz, 1H), 6.82 (br, 1H), 7.49 (d, J = 9.2 Hz, 1H),
13
6.49-8.15 (m, 9H); C-NMR (CDCl3) δ: 48.0, 51.6, 55.8, 101.0, 105.9, 109.4, 111.9, 112.4, 113.3, 124.7,
126.7, 127.4, 128.8, 137.3, 137.8, 148.1, 151.9, 155.6, 157.6, 161.5, 162.7; MS (C23H20N2O3), m/z (% rel.
int.): 372 (M+, 34), 330 (30), 253 (43), 239 (7), 183 (100), 149 (14), 105 (10), 91 (80); Anal. Calcd for
C23H20N2O3: C, 74.18; H, 5.41; N, 7.52. Found: C, 74.32; H, 5.56; N, 7.63.