78 Ding, Fu, and Yuan
TABLE 2 The Elemental Analysis, IR, MS, and 1H-NMR Data of 4, 5, and 7
Anal. %, (Calc.)
IR (cm−1
)
MS (m/z, %)
1H-NMR (CDCl3, δ)
4aa C, 54.71 (54.78); H, 4.02
3316, 3288,
1711, 1613
219 (M+, 69), 188 (11), 5.22 (s, 2H, NH2), 6.64 (s, 1H, CH),
(4.14); N, 19.25 (19.16)
190 (25), 147 (99),
132 (100)
7.40–7.78 (m, 5H, Ar-H), 12.24 (s, 1H, NH)
4ba C, 53.18 (53.00); H, 4.55
3321, 3211,
1681, 1595
249 (M+, 93), 218 (14), 3.82 (s, 3H, OCH3), 5.20 (s, 2H, NH2), 6.68
(4.45); N, 16.84 (16.86)
190 (25), 147 (99),
132 (100)
(s, 1H, CH), 6.87–7.72 (m, 4H, Ar-H),
12.20 (s, 1H, NH)
4ca C, 47.27 (47.34); H, 3.22
3323, 3274,
1713, 1607
255 (24), 253 (M+, 62), 5.22 (s, 2H, NH2), 6.63 (s, 1H, CH),
(3.18); N, 19.61 (16.56)
222 (10), 194 (31), 89
(100)
7.48–7.80 (m, 4H, Ar-H), 12.28 (s, 1H, NH)
4da C, 45.84 (45.93); H, 3.16
3328, 3246,
1723, 1651
3327, 3216,
1712, 1627
3321, 3215,
1701, 1631
209 (M+, 77), 178 (8),
150 (30), 107 (100)
5.20 (s, 2H, NH2), 6.55 (s, 1H, CH),
6.68–7.88 (m, 3H, Ar-H), 11.90 (s, 1H, NH)
(3.37); N, 20.15 (20.08)
5a
5b
C, 56.68 (56.63); H, 4.69
(4.75); N, 18.05 (18.01)
C, 54.80 (54.74); H, 4.97
(4.98); N, 15.88 (15.96)
233 (M+, 80), 216 (12), 2.66 (s, 3H, SCH3), 4.18 (s, 2H, NH2), 6.96
116 (62), 89 (100)
(s, 1H, CH), 7.37–8.17 (m, 5H, Ar-H)
263 (M+, 89), 248 (16), 2.67 (s, 3H, SCH3), 3.86 (s, 3H, OCH3), 4.17
146 (48), 89 (100)
(s, 2H, NH2), 6.94–8.15 (m, 5H, Ar-H, and
CH)
5c
5d
5e
C, 48.36 (48.42); H, 4.11
(4.06); N, 18.85 (18.82)
C, 49.25 (49.35); H, 3.81
(3.76); N, 15.67 (15.69)
C, 58.23 (58.28); H, 5.38
(5.30); N, 16.96 (16.99)
3323, 3212,
1701, 1621
3332, 3206,
1706, 1626
3343, 3277,
1710, 1634
223 (M+, 85), 206 (14), 2.65 (s, 3H, SCH3), 4.20 (s, 2H, NH2), 6.92
106 (39), 89 (100)
(s, 1H, CH), 6.58–7.59 (m, 3H, Ar-H)
267 (M+, 40), 269 (14), 2.67 (s, 3H, SCH3), 4.17 (s, 2H, NH2), 6.89
150 (17), 89 (100)
247 (M+, 2), 202 (3),
160 (4), 116 (100)
(s, 1H, CH), 7.37–8.11 (m, 4H, Ar-H)
1.51 (s, 3H, J = 7.2 Hz, CH3), 3.29 (q, 2H,
J = 7.2 Hz, SCH2), 4.16 (s, 2H, NH2), 6.95
(s, 1H, CH), 7.37–8.16 (m, 5H, Ar-H)
5f
C, 59.87 (59.75); H, 5.78
(5.79); N, 16.14 (16.08)
3340, 3263,
1724, 1631
261 (M+, 55), 219 (95), 1.10–1.92 (m, 5H, CH2CH3), 3.26 (t, 2H,
160 (26), 75 (100)
J = 7.2 Hz, SCH2), 4.16 (s, 2H, NH2), 6.95
(s, 1H, CH), 7.37–8.17 (m, 5H, Ar-H)
5g
5h
5i
C, 60.74 (60.68); H, 4.24
(4.31); N, 16.46 (16.33)
3331, 3286,
2220, 1704,
1622
3348, 3277,
1742, 1714,
1631
3347, 3275,
1742, 1713,
1634
3338, 3262,
1746, 1715,
1636
3348, 3277,
1745, 1710,
1633
3327, 3269,
1713, 1696,
1634
3318, 3278,
1711, 1698,
1635
3312, 3277,
1710, 1636
1734, 1634,
1512, 1201
257 (M+, 72), 241 (77), 2.31 (s, 1H, C≡CH), 4.04 (s, 2H, SCH2), 4.18
160 (62), 116 (100)
(s, 2H, NH2), 6.99 (s, 1H, CH), 7.41–8.17
(m, 5H, Ar-H)
3.81 (s, 3H, OCH3), 4.01 (s, 2H, SCH2), 4.19
(s, 2H, NH2), 6.97 (s, 1H, CH), 7.40–8.12
(m, 5H, Ar-H)
C, 53.41 (53.60); H, 4.37
(4.50); N, 14.54 (14.42)
291 (M+, 100), 260
(45), 231 (74), 147
(96)
C, 53.55 (53.33); H, 4.85
(4.70); N, 13.03 (13.08)
321 (M+, 56), 290 (13), 3.80 (s, 3H, OCH3), 3.87 (s, 3H, OCH3), 4.01
262 (38), 147 (100)
(s, 2H, SCH2), 4.18 (s, 2H, NH2),
6.93–8.10 (m, 5H, Ar-H and CH)
3.79 (s, 3H, OCH3), 4.00 (s, 2H, SCH2), 4.20
(s, 2H, NH2), 6.94 (s, 1H, CH), 6.59–7.58
(m, 3H, Ar-H)
3.80 (s, 3H, OCH3), 4.00 (s, 2H, SCH2), 4.20
(s, 2H, NH2), 6.90 (s, 1H, CH), 7.37–8.06
(m, 4H, Ar-H)
5j
C, 46.87 (46.97); H, 3.90
(3.94); N, 15.06 (14.94)
281 (M+, 100), 250
(11), 222 (50), 106
(64)
5k
5la
C, 47.80 (47.93); H, 3.62
(3.71); N, 12.97 (12.90)
325 (M+, 100), 293
(14), 266 (62), 147
(92)
C, 64.23 (64.08); H, 4.56
(4.48); N, 12.33 (12.45)
337 (M+, 66), 319 (99), 4.88 (s, 2H, SCH2), 5.47 (s, 2H, NH2), 6.77
232 (65), 105 (100)
(s, 1H, CH), 6.95–8.18 (m, 10H, Ar-H)
5ma C, 62.17 (62.11); H, 4.58
367 (M+, 60), 349 (64), 3.77 (s, 3H, OCH3), 4.83 (s, 2H, SCH2), 5.30
(4.66); N, 11.56 (11.44)
335 (49), 262 (57),
105 (100)
(s, 2H, NH2), 6.89–8.07 (m, 10H, Ar-H, and
CH)
5na C, 58.48 (58.70); H, 4.16
327 (M+, 47), 309 (58), 4.86 (s, 2H, SCH2), 5.44 (s, 2H, NH2), 6.98
(4.00); N, 12.76 (12.84)
C, 67.62 (67.69); H, 4.16
265 (43), 105 (100)
319 (M+, 100), 291
(23), 175 (59), 116
(90)
(s, 1H, CH), 6.63–8.14 (m, 8H, Ar-H)
4.04 (s, 2H, SCH2), 7.23 (s, 1H, CH),
7.43–8.16 (m, 10H, Ar-H)
7a
(4.10); N, 13.04 (13.16)
7b
7c
C, 65.24 (65.31); H, 4.28
(4.33); N, 12.15 (12.03)
C, 62.17 (62.12); H, 3.64
(3.58); N, 13.48 (13.58)
1725, 1635,
1597, 1256
1721, 1635,
1499, 1240
349 (M+, 83), 321 (18), 3.87 (s, 3H, OCH3), 4.03 (s, 2H, SCH2), 7.20
175 (29), 146 (100)
309 (M+, 92), 281 (28), 4.03 (s, 2H, SCH2), 6.60–7.89 (m, 9H, Ar-H,
175 (69), 117 (100) and CH)
(s, 1H, CH), 6.95–8.15 (m, 9H, Ar-H)
a1H NMR were recorded in DMSO-d6.