80
F.-L. Yang, Z.-J. Liu, X.-B. Huang and M.-W. Ding
Vol. 41
Table 4
-1
IR (KBr, ν/cm ) , and EI-MS Data of Compounds 4a – t
No.
ν
;
ν
;
ν
;
ν
C=N & C=C (in ring)
m/z (abundance, %)
CO Et
2
C=O
C=C
+
4a
4b
4c
4d
4e
4f
4g
4h
4i
1700;
1708;
1702;
1696;
1712;
1708;
1704;
1707;
1714;
1710;
1702;
1709;
1705;
1708;
1707;
1709;
1702;
1713;
1706;
1707;
1638;
1639;
1638;
1634;
1642;
1633;
1642;
1632;
1640;
1634;
1626;
1632;
1636;
1642;
1634;
1631;
1632;
1632;
1633;
1642;
1488, 1468
1491, 1466
1492, 1468
1487, 1465
1493, 1468
1493, 1469,1433
1494, 1474, 1461
1590, 1568, 1488, 1466, 1419
1592, 1568, 1494, 1469, 1421
1577, 1556, 1491, 1463, 1418
1556, 1490, 1462, 1427
1582, 1489, 1468, 1453
1615, 1590, 1551, 1469
1592, 1493, 1470, 1448
1599, 1554, 1492, 1465
1558, 1512, 1487, 1467
1551, 1491, 1463, 1422
1554, 1492, 1463, 1444
1598, 1578, 1493, 1465
1571, 1494, 1468, 1437
278(M , 86); 236(90); 107(100)
+
1729;
322(M , 100); 236(63); 107(70)
+
264(M , 100); 236(17); 107(52)
+
346(M , 40); 290(40); 97(100)
+
1731;
1735;
1736;
376(M , 67); 289(28); 97(100)
+
321(M , 12); 274(65); 100(100)
+
393(M , 7); 274(68); 100(100)
+
299(M , 36); 252(100); 106(22)
+
385(M , 90); 252(100); 106(50)
+
4j
4k
4l
299(M , 85); 252(60); 92(100)
+
316(M , 75); 283(6); 109(100)
+
1729;
1740;
1741;
1730;
1738;
388(M , 66); 315(65); 109(100)
+
4m
4n
4o
4p
4q
4r
4s
4t
316(M , 99); 283(39); 109(100)
+
388(M , 87); 315(58); 109(100)
+
316(M , 82); 283(5); 109(100)
+
388(M , 47); 315(20); 109(100)
+
333(M , 32); 297(86); 125(100)
+
405(M , 7); 369(57); 125(100)
+
333(M , 25); 332(100); 125(87)
+
405(M , 37); 331(65); 125(100)
Table 5
1
H NMR Data of Compounds 2, 3a - k and 4a - t
1
No.
H NMR (δ/ppm, 300MHz, CDCl )
3
2
7.64 - 6.47(m, 3H, Furyl-H); 7.72(s, 1H, =CH); 4.39 - 4.32(q, 2H, OC H CH , J=6.9 Hz); 1.42 - 1.37(t, 3H, OCH CH , J = 6.9 Hz).
2 3 2 3
3a
9.24(bs, 1H, NH); 7.61 - 6.48(m, 3H, Furyl-H); 6.68(s, 1H, =CH); 3.88 - 3.63(t, 2H, NCH , J = 7.4 Hz); 1.81 - 1.69(m, 2H,
NCH CH ); 0.99 - 0.94(t, 3H, CH , J = 7.8 Hz).
2
2
9.23(bs, 1H, NH); 7.60 - 6.47(m, 3H, Furyl-H); 6.68(s, 1H, =CH); 3.91 - 3.86(t, 2H, NCH , J = 7.3 Hz); 1.72 - 1.65(m, 2H,
2
3
3b
2
NCH CH ); 1.42 - 1.34(m, 2H, CH CH ); 0.98 - 0.93(t, 3H, CH , J = 7.3 Hz).
2
9.30(bs, 1H, NH); 7.60 - 6.47(m, 3H, Furyl-H); 7.26 - 6.93(m, 3H, Thiophen-yl-H); 6.68(s, 1H, =CH); 5.03(m, 2H, NCH ).
2
2
3
3
3c
2
3d
9.25(bs, 1H, NH); 7.60 - 6.47(m, 3H, Furyl-H); 6.68(s, 1H, =CH); 4.04 - 4.01(m, 2H, NCH , J = 5.9 Hz); 3.65 - 3.61(m, 4H,
2
CH OCH ); 2.69(s, 2H, CH N(CH ) ); 2.54(s, 4H, CH N( C H ) ).
2
9.37(bs, 1H, NH); 8.52 - 7.13(m, 4H, Pyridyl-H); 7.60 - 6.53(m, 3H, Furyl-H); 6.69(s, 1H, =CH); 5.24(s, 2H, NCH ).
2
2
2 2 2 2
2
3e
3f
3g
3h
3i
2
9.38(bs, 1H, NH); 8.74 - 7.21(m, 4H, Pyridyl-H); 7.61 - 6.50(m, 3H, Furyl-H); 6.70(s, 1H, =CH); 5.09(s, 2H, NCH ).
9.36(bs, 1H, NH); 7.61 - 6.51(m, 3H, Furyl-H); 7.25 - 7.00(m, 4H, Ar-H); 6.70(s, 1H, =CH); 5.17 (s, 2H, NCH ).
2
2
9.33(bs, 1H, NH); 7.60 - 6.49(m, 3H, Furyl-H); 7.26 - 6.91(m, 4H, Ar-H); 6.68(s, 1H, =CH); 5.06 (s, 2H, NCH ).
2
9.26(bs, 1H, NH); 7.60 - 6.48(m, 3H, Furyl-H); 7.49 - 6.94(m, 4H, Ar-H); 6.68(s, 1H, =CH); 5.31 (s, 2H, NCH ).
2
3j
9.44(bs, 1H, NH); 7.62 -6.54(m, 3H, Furyl-H); 7.37 - 6.99(m, 4H, Ar-H); 6.71(s, 1H, =CH); 5.21 (s, 2H, NCH ).
2
3k
4a
9.29(bs, 1H, NH); 7.60 - 6.49(m, 3H, Furyl-H); 7.43 - 7.21(m, 4H, Ar-H); 6.69(s, 1H, =CH); 5.04 (s, 2H, NCH ).
2
7.53 - 6.54(m, 3H, Furyl-H); 6.86(s, 1H, =CH); 3.55 - 3.50(t, 2H, NCH , J = 7.5 Hz); 3.35 - 3.30 (t, 2H, SCH , J = 7.2 Hz);
2
1.91 - 1.81(m, 2H, NCH CH ); 1.75 - 1.61(m, 2H, SCH CH ); 1.12 – 1.07(t, 3H, NCH CH CH , J = 7.2 Hz); 0.95 - 0.91(t, 3H,
2
2
2
2
2
2
2
3
SCH CH CH , J = 7.2 Hz).
2
7.53 - 6.54(m, 3H, Furyl-H); 6.89(s, 1H, =CH); 4.26 - 4.19(q, 2H, OCH , J = 7.2 Hz); 4.07(s, 2H, SCH ); 3.58 - 3.53(t, 2H, NCH ,
2
3
4b
2 2 2
J = 7.4 Hz); 1.74 - 1.64(q, 2H, NCH CH , J = 7.4 Hz); 1.31-1.26 (t, 3H, OCH CH , J = 7.2 Hz); 0.97 - 0.92(t, 3H, NCH CH CH ,
2
2
2
3
2
2
3
J = 7.4 Hz).
7.54 - 6.54(m, 3H, Furyl-H); 6.87(s, 1H, =CH); 3.60 - 3.55(t, 2H, NCH , J = 7.4 Hz); 2.72(s, 3H, SCH ); 1.68 - 1.58(m, 2H,
4c
4d
4e
4f
2
3
NCH CH ); 1.40 - 1.30(m, 2H, CH CH ); 0.96 - 0.91(t, 3H, CH CH , J = 7.4 Hz).
2
2
2
3
7.57 - 6.56(m, 3H, Furyl-H); 7.26 - 6.93(m, 3H, Thiophen-yl-H); 6.94(s, 1H, =CH); 4.93(s, 2H, N-CH ); 3.42 - 3.73(t, 2H, SCH ,
2
3
2
J = 6.9 Hz); 1.89 - 1.80(m, 2H, SCH CH ); 1.59 - 1.47(m, 2H, SCH CH CH CH ); 1.03 - 0.98(t, 3H, CH CH , J = 7.4 Hz).
2
2
2
2
2
2
3
2
3
7.53 - 6.54(m, 3H, Furyl-H); 7.23 - 6.91(m, 3H, Thiophen-yl-H); 6.93(s, 1H, =CH); 4.93(s, 2H, NCH ); 4.25 - 4.18(q, 2H, OCH ,
2
2
J = 7.2 Hz); 4.04(s, 2H, SCH ); 1.30 - 1.25(t, 3H, OCH CH , J = 7.2 Hz).
2
7.55 - 6.53(m, 3H, Furyl-H); 6.87(s,1H, =CH); 3.72 - 3.64(m, 6H, NCH and CH OCH ); 2.73(s, 3H, SCH ); 2.60 - 2.56(m, 2H,
2
3
2
2
2
3
NCH CH ); 2.52 - 2.46(m, 4H, N(CH ) ).
2 2
2
7.54 - 6.55(m, 3H, Furyl-H); 6.89(s, 1H, =CH); 4.26 - 4.20(q, 2H, OC H CH , J = 6.9 Hz); 4.07(s, 2H, SCH ); 3.71 - 3.67(m, 6H, NCH
2
4g
2 3 2 2
and CH OCH ); 2.61 - 2.57(t, 2H, NCH CH , J= 6.2 Hz); 2.52 - 2.47(m, 4H, N(CH ) ); 1.32 - 1.27(t, 3H, OCH CH , J = 6.9 Hz).
2 2
2
2
2
2
8.54 - 7.15(m, 4H, Pyridyl-H); 7.55 - 6.55(m, 3H, Furyl-H); 6.95(s, 1H, =CH); 4.92(s, 2H, NCH ); 2.68(s, 3H, SCH ).
2
3
4h
4i
2 3
8.53 - 7.17(m, 4H, Pyridyl-H); 7.53 - 6.55(m, 3H, Furyl-H); 6.94(s, 1H, =CH); 4.96 - 4.82(m, 2H, NCH ); 4.61 - 4.54(q, 1H, SCH,
2
J = 7.2 Hz); 4.28 - 4.10(m, 2H, OCH ); 1.68 - 1.65(d, 3H, SCH (M e), J = 6.9 Hz); 1.27 – 1.20(m, 3H, OCH CH ).
2
8.59 - 7.20(m, 4H, Pyridyl-H); 7.55 - 6.55(m, 3H, Furyl-H); 6.93(s, 1H, =CH); 4.77(s, 2H, NCH ); 2.69(s, 3H, SCH ).
2
3
4j
2 3