ONE-POT SYNTHESES OF COUMARIN DYES
907
8.9 Hz, 4JHH 2.3 Hz, CH), 7.29 (1H, dd, 3JHH 8.3 Hz, 4JHH 1.9 Hz, CH), 7.42 (1H, d,
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4
3JHH 8.9 Hz, CH), 7.50 (1H, d, JHH 8.3 Hz, CH), 7.75 (1H, d, JHH 1.9 Hz, CH),
8.61 (1H, s, CH); 13C NMR (125.7 MHz, DMSO-d6): dC 13.2 (2CH3), 45.3
(2CH2), 96.9 (CH), 104.9 (CH), 108.5 (C), 110.9 (CH), 112.7 (CH), 119.7 (CH),
125.7 (CH), 129.7 (C), 132.3 (CH), 143.6 (C), 147.3 (C), 149.5 (C), 153.5 (C),
157.5 (C), 158.3 (C), 162.4 (C). Anal. calcd. for C20H17N2O3Cl (368.5): C, 65.13;
H, 4.61; N, 7.60%. Found: C, 65.16; H, 4.64; N, 7.58%.
3-(5-Methyl-2-benzoxazolyl)-7-(diethylamino)-2H-1-benzopyran-2-one
4b. Yellow powder; mp 208–210 ꢀC; IR (KBr) (nmax=cmꢂ1): 2969, 2924, 1739, 1615,
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1583, 1549. H NMR (500 MHz, CDCl3): dH 1.25 (6H, t, JHH 7.2 Hz, 2 CH3), 2.47
(3H, s, CH3), 3.46 (4H, q, 3JHH 7.2 Hz, 2 CH2), 6.54 (1H, d, 4JHH 2.0 Hz, CH), 6.64
(1H, dd, 3JHH 8.9 Hz, 4JHH 2.0 Hz, CH), 7.13 (1H, d, 3JHH 8.2 Hz, CH), 7.41 (1H, d,
3JHH 8.9 Hz, CH), 7.45 (1H, d, 3JHH 8.2 Hz, CH), 7.57 (1 H, s, CH), 8.60 (1H, s, CH);
13C NMR (125.7 MHz, DMSO-d6): dC 13.2 (2 CH3), 21.9 (CH3), 45.2 (2 CH2), 96.9
(CH), 105.8 (CH), 108.5 (C), 110.8 (CH), 111.3 (CH), 120.0 (CH), 126.9 (CH), 132.1
(CH), 134.8 (C), 142.5 (C), 146.8 (C), 149.2 (C), 153.2 (C), 157.8 (C), 158.2 (C), 160.8
(C). Anal. calcd. for C21H20N2O3 (348): C, 72.41; H, 5.75; N, 8.04%. Found: C,
72.44; H, 5.73; N, 8.07%.
3-(2-Benzoxazolyl)-7-(diethylamino)-2H-1-benzopyran-2-one 4c. Yellow
powder; mp 184–186 ꢀC; IR (KBr) (nmax=cmꢂ1): 2971, 2927, 1738, 1609, 1588,
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1550. H NMR (500 MHz, DMSO-d6): dH 1.11 (6H, t, JHH 7.0 Hz, 2 CH3), 3.45
(4H, q, JHH 7.0 Hz, 2 CH2), 6.55 (1H, d, JHH 1.7 Hz, CH), 6.76 (1H, dd, JHH
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4
3
4
3
8.9 Hz, JHH 1.7 Hz, CH), 7.35 (2H, m, 2 CH), 7.64 (1H, d, JHH 8.9 Hz, CH),
7.70 (2H, m, 2 CH), 8.74 (1H, s, CH); 13C NMR (125.7 MHz, DMSO-d6): dC 13.2
(2 CH3), 45.2 (2 CH2), 96.9 (CH), 105.6 (CH), 108.5 (C), 110.8 (CH), 111.4 (CH),
120.2 (CH), 125.5 (CH), 125.9 (CH), 132.2 (CH), 142.3 (C), 147.0 (C), 150.7 (C),
153.5 (C), 157.7 (C), 158.3 (C), 160.8 (C). Anal. calcd. for C20H18N2O3 (334): C,
71.85; H, 5.39; N, 8.38%. Found: C, 71.87; H, 5.36; N, 8.40%.
3-(5-Ethylsulphonyl-2-benzoxazolyl)-7-(diethylamino)-2H-1-benzopyran-
2-one 4d. Yellow powder; mp 200–202 ꢀC; IR (KBr) (nmax=cmꢂ1): 2977, 2935, 1729,
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1634, 1590, 1521. H NMR (500 MHz, CDCl3): dH 1.23 (3H, t, JHH 7.3 Hz, CH3),
1.25 (6H, t, JHH 7.1 Hz, 2 CH3), 3.17 (2H, q, JHH 7.3 Hz, CH2), 3.48 (4H, q, JHH
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3
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4
7.1 Hz, 2 CH2), 6.55 (1H, d, JHH 2.1 Hz, CH), 6.67 (1H, dd, JHH 8.9 Hz, JHH
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4
3
3
2.1 Hz, CH), 7.45 (1H, d, JHH 8.9 Hz, CH), 7.74 (1H, d, JHH 8.5 Hz, CH), 7.90
3
4
4
(1H, dd, JHH 8.5 Hz, JHH 1.6 Hz, CH), 8.33 (1H, d, JHH 1.6 Hz, CH), 8.66 (1H,
s, CH); 13C NMR (125.7 MHz, DMSO-d6): dC 13.16 (CH3), 13.23 (2 CH3), 45.3
(CH2), 45.4 (2 CH2), 96.9 (CH), 104.5 (CH), 108.5 (C), 111.0 (CH), 111.2 (CH),
120.1 (CH), 125.7 (CH), 132.2 (CH), 136.0 (C), 142.7 (C), 147.8 (C), 152.8 (C),
153.7 (C), 157.6 (C), 158.3 (C), 163.2 (C). Anal. calcd. for C22H22N2O6S (442): C,
59.73; H, 4.98; N, 6.33%. Found: C, 59.75; H, 4.95; N, 6.35%.
3-(-2-Benzimidazolyl)-7-(diethylamino)-2H-1-benzopyran-2-one 4e. Yellow
powder; mp 218–220 ꢀC; IR (KBr) (nmax=cmꢂ1): 3338, 2972, 2931, 1692, 1619,
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1591, 1529. 1H NMR (500 MHz, DMSO-d6): dH 1.11 (6H, t, JHH 7.0 Hz, 2
CH3), 3.43 (4H, q, JHH 7.0 Hz, 2 CH2), 6.61 (1H, d, JHH 1.7 Hz, CH), 6.76
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4
3
4
(1H, dd, JHH 8.9 Hz, JHH 1.7 Hz, CH), 7.12 (1H, m, 2 CH), 7.57 (2H, m,