508
A. K. Patel, N. H. Patel, M. A. Patel, and D. I. Brahmbhatt
Vol 49
(CH3), 112.38(CH), 116.38(CH), 119.75(C), 120.55(CH), 121.40
(CH), 123.33(C), 123.63(CH), 124.57(CH), 125.72(C), 128.82
(CH), 128.85(CH), 129.38(CH), 129.71(CH), 130.94(C), 131.91
(CH), 132.07(C), 139.63(C), 142.30(CH), 144.75(C), 147.00(C),
147.72(C), 153.86(C), 157.84(C), 160.63(C). Anal. Calcd. for
C27H17NO3: C, 80.38; H, 4.25; N, 3.47. Found: C, 80.28; H,
4.13; N, 3.53; MS: m/z 403 (M+)
3-(4-(4-Methoxyphenyl)benzofuro[3,2-b]pyridin-2-yl)coumarin
(3c). Yield 58%; m.p. 228–230ꢁC; IR: cmꢀ1 1730, 1600, 1465, 1100;
1H-NMR: d 3.94 (3H, s, OCH3), 7.13–8.35 (12H, m, Ar-H), 8.75 (1H,
s, C3’-H), 8.97 (1H, s, C4-H); 13C-NMR: d 55.44(OCH3), 112.36
(CH), 114.44(CH), 116.37(CH), 119.79(C), 120.19(CH), 121.40
(CH), 123.39(C), 123.63(CH), 124.57(CH), 125.79(C), 126.16(C),
128.81(CH), 129.34(CH), 130.35(CH), 131.75(C), 131.88(CH),
142.29(CH), 144.71(C), 146.90(C), 147.72(C), 153.88(C), 157.80
(C), 160.67(C). Anal. Calcd. for C27H17NO4: C, 77.32; H, 4.09; N,
3.34. Found: C, 77.45; H, 4.19; N, 3.23; MS: m/z 419 (M+)
8-Methoxy-3-(4-(4-methylphenyl)benzofuro[3,2-b]pyriꢀdi1n-2-yl)
coumarin (3h). Yield 52%; m.p. 263–264ꢁC; IR: cm 1720,
1
1600, 1480, 1105; H-NMR: d 2.49 (3H, s, CH3), 4.04 (3H, s,
OCH3), 7.14–8.36 (11H, m, Ar-H), 8.78 (1H, s, C3’-H), 8.96 (1H,
s, C4-H); 13C-NMR: d 21.44(CH3), 56.33(OCH3), 112.41(CH),
113.68(CH), 120.28(CH), 120.46(CH), 120.59(C), 120.71(CH),
121.40(CH), 122.63(C), 123.39(C), 123.63(CH), 124.41(CH),
126.04(C), 128.90(CH), 129.37(C), 129.73(CH), 130.95(C),
132.19(C), 138.73(C), 139.61(C), 142.46(CH), 144.73(C), 146.95
(C), 157.87(C), 160.06(C). Anal. Calcd. for C28H19NO4: C, 77.59;
H 4.42; N, 3.23. Found: C, 77.42; H, 4.29; N, 3.11; MS: m/z
433 (M+)
8-Methoxy-3-(4-(4-methoxyphenyl)benzofuro[3,2-b]pyridin-
2-yl)coumarin (3i).
Yield 54%; m.p. 268–270ꢁC; IR: cmꢀ1
1
1715, 1600, 1480, 1105; H-NMR: d 3.94 and 4.04 (6H, two s,
2 ꢂ OCH3), 7.13–8.63 (11H, m, Ar-H), 8.78 (1H, s, C3’-H),
8.96 (1H, s, C4-H); 13C-NMR: d 55.44(OCH3), 56.32(OCH3),
110.19(C), 112.39(CH), 113.72(CH), 114.45(CH), 120.27(CH),
120.30(CH), 120.46(C), 121.44(CH), 123.66(CH), 124.43(CH),
126.16(C), 129.34(CH), 130.41(CH), 131.86(C), 136.15(C),
136.69(C), 142.26(C), 142.49(CH), 144.18(C), 146.96(C),
147.74(C), 156.28(C), 157.83(C), 160.67(C). Anal. Calcd. for
C28H19NO5: C, 74.82; H, 4.26; N, 3.12. Found: C, 74.98; H,
4.38; N, 3.28; MS: m/z 449 (M+)
3-(8-Methyl-4-phenylbenzofuro[3,2-b]pyridinꢀ-21-yl)coumarin
(3d).
Yield 57%; m.p. 252–253ꢁC; IR: cm 1725, 1600,
1
1475, 1100; H-NMR: d 2.58 (3H, s, CH3), 7.36–8.12 (12H, m,
Ar-H), 8.76 (1H, s, C3’-H), 8.96 (1H, s, C4-H); 13C-NMR: d
21.39(CH3), 111.89(CH), 116.38(CH), 119.77(C), 120.59(CH),
121.23(CH), 123.22(C), 124.59(CH), 125.67(C), 128.79(CH),
128.98(CH), 129.40(CH), 130.64(CH), 131.90(CH), 133.37(C),
133.93(C), 135.19(C), 142.21(CH), 144.85(C), 147.51(C),
153.85(C), 156.28(C), 156.32(C), 160.63(C). Anal. Calcd. for
C27H17NO3: C, 80.38; H, 4.25; N, 3.47. Found: C, 80.28; H,
4.31; N, 3.45; MS: m/z 403 (M+)
8-Methoxy-3-(8-methyl-4-phenylbenzofuro[3,2-b]pyriꢀd1in-2-yl)
coumarin (3j). Yield 52%; m.p. 218–220ꢁC; IR: cm 1715,
1
1605, 1480, 1100; H-NMR: d 2.57 (3H, s, CH3), 4.02 (3H, s,
OCH3), 7.11–8.11 (11H, m, Ar-H), 8.76 (1H, s, C3’-H), 8.93
(1H, s, C4-H); 13C-NMR: d 21.35(CH3), 56.28(OCH3), 111.87
(CH), 113.61(CH), 120.23(CH), 120.41(C), 120.63(CH), 121.21
(CH), 123.24(C), 124.37(CH), 125.86(C), 128.93(CH), 129.00
(CH), 129.35(CH), 130.60(CH), 131.91(C), 133.33(C), 133.95
(C), 142.33(CH), 143.52(C), 144.79(C), 146.91(C), 147.27(C),
147.51(C), 156.31(C), 160.01(C). Anal. Calcd. for C28H19NO4:
C, 77.59; H, 4.42; N, 3.23. Found: C, 77.67; H, 4.51; N, 3.37;
MS: m/z 433 (M+)
3-(8-Methyl-4-(4-methylphenyl)benzofuro[3,2-b]pyridin-2-yl)
coumarin (3e). Yield 59%; m.p. 218–219ꢁC; IR: cmꢀ1 1730, 1605,
1475, 1100; 1H-NMR: d 2.48 and 2.58 (6H, two s, 2 ꢂ CH3), 7.34–
8.11 (11H, m, Ar-H), 8.73 (1H, s, C3’-H), 8.94 (1H, s, C4-H); 13C-
NMR: d 21.35(CH3), 21.44(CH3), 111.86(CH), 116.35(CH), 119.79
(C), 120.35(CH), 121.18(CH), 123.28(C), 124.54(CH), 125.78(C),
128.77(CH), 128.83(CH), 129.67(CH), 130.53(CH), 131.00(C),
131.81(CH), 131.90(C), 133.27(C), 139.53(C), 142.13(CH), 144.74
(C), 147.47(C), 153.85(C), 156.27(C), 160.60(C). Anal. Calcd. for
C28H19NO3: C, 80.56; H, 4.59; N, 3.36. Found: C, 80.64; H, 4.68;
N, 3.47; MS: m/z 417 (M+)
8-Methoxy-3-(8-methyl-4-(4-methylphenyl)benzofuro[3,2-b]
pyridin-2-yl)coumarin (3k). Yield 55%; m.p. 255–257ꢁC; IR:
1
cmꢀ1 1715, 1595, 1480, 1105; H-NMR: d 2.48 and 2.58 (6H,
3-(8-Methyl-4-(4-methoxyphenyl)benzofuro[3,2-b]pyridin-2-
yl)coumarin (3f).
two s, 2 ꢂ CH3), 4.03 (3H, s, OCH3), 7.13–8.13 (10H, m, Ar-
H), 8.75 (1H, s, C3’-H), 8.93 (1H, s, C4-H); 13C-NMR: d
21.35(CH3), 21.43(CH3), 56.30(OCH3), 109.69(C), 111.88
(CH), 113.62(CH), 120.23(CH), 120.47(CH), 121.19(CH),
123.31(C), 124.37(CH), 126.04(C), 128.88(CH), 129.67(CH),
130.53(CH), 131.02(C), 132.00(C), 133.28(C), 139.52(C),
142.33(CH), 143.54(C), 144.74(C), 146.93(C), 147.33(C),
147.53(C), 156.29(C), 160.05(C). Anal. Calcd. for
C29H21NO4: C, 77.84; H, 4.73; N, 3.13. Found: C, 77.98; H,
4.86; N, 3.27; MS: m/z 447 (M+)
Yield 54%; m.p. 223–224ꢁC; IR: cmꢀ1
1725, 1605, 1480, 1105; 1H-NMR: d 2.57 (3H, s, CH3), 3.93
(3H, s, OCH3), 7.11–8.11 (11H, m, Ar-H), 8.72 (1H, s, C3’-H),
8.94 (1H, s, C4-H); 13C-NMR: d 21.37(CH3), 55.43(OCH3),
111.84(CH), 114.39(CH), 116.35(CH), 119.79(C), 119.96(CH),
121.19(CH), 123.27(C), 124.56(CH), 125.76(C), 126.21(C),
128.78(CH), 130.33(CH), 130.51(CH), 131.55(C), 131.83(CH),
133.27(C), 142.16(CH), 144.69(C), 147.14(C), 147.43(C),
153.83(C), 156.22(C), 160.59(C), 160.64(C). Anal. Calcd. for
C28H19NO4: C, 77.59; H, 4.42; N, 3.23. Found: C, 77.48; H,
4.30; N, 3.17; MS: m/z 433 (M+)
8-Methoxy-3-(8-methyl-4-(4-methoxyphenyl)benzofuro[3,2-
b]pyridin-2-yl)coumarin (3l). Yield 52%; m.p. 262–264ꢁC; IR:
1
8-Methoxy-3-(4-phenylbenzofuro[3,2-b]pyridin-2-yl)ꢀ1
cmꢀ1 1715, 1600, 1475, 1100; H-NMR: d 2.58 (3H, s, CH3),
coumarin (3g). Yield 61%; m.p. 248–249ꢁC; IR: cm 1715,
3.93 and 4.04 (6H, two s, 2 ꢂ OCH3), 7.12–8.13 (10H, m, Ar-
H), 8.75 (1H, s, C3’-H), 8.94 (1H, s, C4-H); 13C-NMR: d
21.34(CH3), 55.43(OCH3), 56.31(OCH3), 111.85(CH), 113.63
(CH), 114.40(CH), 120.09(CH), 120.23(CH), 120.47(C),
121.20(CH), 123.34(C), 124.37(CH), 126.07(C), 126.25(C),
130.36(CH), 130.49(CH), 133.63(C), 133.27(C), 142.31(CH),
143.55(C), 144.71(C), 146.94(C), 147.21(C), 147.51(C),
156.25(C), 160.06(C), 160.61(C). Anal. Calcd. for
C29H21NO5: C, 75.15; H, 4.57; N, 3.02. Found: C, 75.28; H,
4.68; N, 3.12; MS: m/z 463 (M+).
1
1605, 1485, 1100; H-NMR: d 4.04 (3H, s, OCH3), 7.14–8.37
(12H, m, Ar-H), 8.81 (1H, s, C3’-H), 8.97 (1H, s, C4-H); 13C-
NMR: d 56.31(OCH3), 112.44(CH), 113.74(CH), 120.28(CH),
120.44(C), 120.91(CH), 121.45(CH), 123.35(C), 123.71(CH),
124.43(CH), 125.92(C), 128.94(CH), 129.02(CH), 129.45(CH),
132.18(C), 133.91(C), 142.53(CH), 143.58(C), 144.84(C),
146.96(C), 147.06(C), 147.83(C), 157.92(C), 160.06(C). Anal.
Calcd. for C27H17NO4: C, 77.32; H, 4.09; N, 3.34. Found: C,
77.48; H, 4.13; N, 3.40; MS: m/z 419 (M+)
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet