562
F. F. Wong et al.
LETTER
Compound 2c: 1H NMR (300 MHz, CDCl3): d = 1.14–1.55
(m, 6 H), 1.77–1.96 (m, 4 H), 3.08–3.12 (m, 1 H, CH), 3.43
(br, 1 H, NH). 13C NMR (75 MHz, CDCl3): d = 24.59, 25.18,
32.57, 54.15, 115.89. IR (diffuse reflectance): n = 3216 (m),
2932 (s), 2857 (s), 2217 (s, C≡N), 1694 (s), 1536 (s), 1452
(s), 1318 (m), 1146 (m), 1062 (m) cm–1.
H, ArH), 7.13–7.33 (m, 2 H, ArH). IR (diffuse reflectance):
n = 3415 (m), 2925 (m), 2238 (m, C≡N), 1702 (m), 1618 (w),
1589 (m), 1508 (s), 1456 (s), 1384 (m), 1231 (s), 1175 (m),
1066 (s), 1035 (s), 981 (m), 750 (s) cm–1.
Compound 2k: mp 65–67 °C. 1H NMR (300 MHz, CDCl3):
d = 4.20 (br, 1 H, NH), 3.87 (s, 3 H, OCH3), 6.86–6.91 (m, 1
H, ArH), 6.96–7.05 (m, 1 H, ArH), 7.28–7.39 (m, 2 H, ArH),
Compound 2d: 1H NMR (300 MHz, CDCl3): d = 4.07 (br, 1
H, NH), 6.81 (m, 1 H, ArH), 7.28–7.38 (m, 1 H, ArH), 7.41–
7.64 (m, 2 H, ArH), 7.72–8.05 (m, 2 H, ArH). 13C NMR (75
MHz, CDCl3): d = 109.79, 112.44, 119.04, 120.87, 123.72,
124.90, 125.89, 126.39, 128.59, 134.44, 142.10. IR (diffuse
reflectance): n = 3365 (m), 3051 (m), 2226 (w, C≡N), 1694
(m), 1624 (s), 1577 (m), 1513 (m), 1458 (m), 1405 (m), 1287
(m), 1218 (m), 854 (w), 770 (s) cm–1.
7.40–7.52 (m, 2 H, ArH), 7.55–7.61 (m, 2 H, ArH). 13
C
NMR (75 MHz, CDCl3): d = 55.52, 110.57, 113.76, 117.15,
126.50, 126.70, 126.83, 128.53, 134.23, 136.25, 141.19,
146.95. IR (diffuse reflectance): n = 3376 (m), 2938 (m),
2247 (w, C≡N), 1952 (w), 1715 (m), 1602 (m), 1501 (s),
1248 (s), 1215 (m), 1180 (m), 1151 (m), 1048 (s), 1021 (s),
909 (m), 866 (m), 760 (s) cm–1. Anal. Calcd for C14H12N2O:
C, 74.98; H, 5.39; N, 12.49%. Found: C, 74.96; H, 5.42; N,
12.46%.
Compound 2e: 1H NMR (300 MHz, CDCl3): d = 5.75 (br, 1
H, NH), 7.03 (d, 2 H, J = 8.51 Hz, ArH), 7.11 (t, 1 H,
J = 7.52 Hz, ArH), 7.32 (t, 2 H, J = 7.53 Hz, ArH). 13C NMR
(75 MHz, CDCl3): d = 111.23, 114.38, 122.17, 129.17,
139.63. IR (diffuse reflectance): n = 3283 (m), 2221 (m,
C≡N), 1648 (s), 1593 (s), 1546 (s), 1496 (s), 1447 (s), 1313
(m), 1231 (s), 893 (w), 752 (s), 695 (s) cm–1. MS: m/z
(relative intensity) = 118 (43) [M+], 93 (97), 91 (42), 77 (25).
Compound 2f: 1H NMR (300 MHz, CDCl3): d = 3.68 (br, 1
H, NH), 6.60 (d, 2 H, J = 8.52 Hz, ArH), 7.10 (d, 2 H,
J = 8.51 Hz, ArH). 13C NMR (75 MHz, CDCl3): d = 110.86,
116.63, 128.84, 129.72, 135.82. IR (diffuse reflectance): n =
3374 (m), 2961 (m), 2232 (m, C≡N), 1713 (m), 1600 (m),
1546 (s), 1495 (s), 1403 (m), 1283 (m), 1227 (m), 1092 (s),
821 (s), 639 (m) cm–1. MS: m/z (relative intensity) = 152
(100) [M+], 125 (49), 90 (27), 75 (23).
Compound 2l: 1H NMR (300 MHz, CDCl3): d = 2.09 (s, 3 H,
CH3), 3.54 (br, 2 H, NH), 6.02–6.16 (m, 2 H, ArH), 6.88 (d,
1 H, J = 8.65 Hz, ArH). 13C NMR (75 MHz, CDCl3): d =
102.79, 103.63, 105.74, 105.97, 112.80, 130.92, 145.20,
145.40. IR (diffuse reflectance): n = 3352 (m), 2927 (m),
2219 (m, C≡N), 1622 (s), 1515 (s), 1468 (m), 1321 (m), 1224
(m), 1066 (m), 998 (m), 846 (m), 800 (m), 454 (w) cm–1.
Anal. Calcd for C9H8N4: C, 62.78; H, 4.68; N, 32.54%.
Found: C, 62.76; H, 4.72; N, 32.52%.
Compound 2m: mp 155–157 °C. 1H NMR (300 MHz,
CDCl3): d = 6.63 (d, 4 H, J = 8.64 Hz, ArH), 6.80 (d, 4 H,
J = 8.86 Hz, ArH). 13C NMR (75 MHz, CDCl3): d = 115.26,
116.13, 119.41, 141.57, 150.50. IR (diffuse reflectance): n =
3360 (m), 2952 (m), 2246 (m, C≡N), 1865 (w), 1704 (m),
1629 (m), 1505 (m), 1216 (m), 1036 (m), 910 (m), 871 (m),
830 (m), 733 (m), 513 (m) cm–1.
Compound 2g: 1H NMR (300 MHz, DMSO-d6): d = 5.36 (br,
1 H, NH), 6.51 (m, 1 H, ArH), 7.05 (m, 1 H, ArH), 7.25 (m,
1 H, ArH), 7.68 (m, 1 H, ArH). IR (diffuse reflectance): n =
3192 (m), 2962 (m), 2229 (m, C≡N), 1679 (s), 1597 (s), 1537
(s), 1481 (s), 1424 (m), 1224 (m), 1076 (m), 866 (m), 773
(m), 679 (m) cm–1.
Compound 4a: 1H NMR (300 MHz, acetone-d6): d = 2.94
(br, 1 H, NH), 4.80 (s, 2 H, CH2Cl). IR (diffuse reflectance):
n = 3376 (s, NH), 2958 (s), 2222 (m, C≡N), 1682 (s, C=O),
1529 (m), 1402 (w), 1207 (w), 1045 (m), 917 (w), 768 (m)
cm–1.
Compound 2h: mp 178–180 °C. 1H NMR (300 MHz,
CDCl3): d = 4.32 (br, 1 H, NH), 6.60 (d, 2 H, J = 8.91 Hz,
ArH), 8.06 (d, 2 H, J = 8.88 Hz, ArH). IR (diffuse
reflectance): n = 3360 (m), 2923 (m), 2221 (m, C≡N), 1724
(m), 1630 (s), 1586 (s), 1504 (m), 1469 (s), 1444 (m), 1299
(s), 1113 (s), 999 (m), 839 (s) cm–1.
Compound 4b: mp 131–133 °C. 1H NMR (300 MHz,
CDCl3): d = 6.67 (br, 1 H, NH). 13C NMR (75 MHz, CDCl3):
d = 91.72, 128.33, 163.80. IR (diffuse reflectance): n = 3371
(m), 3247 (m), 2221 (w, C≡N), 1693 (s, C=O), 1610 (m),
1381 (m), 1352 (m), 1108 (m), 928 (w), 831 (s), 750 (m), 649
(m), 617 (m) cm–1. Anal. Calcd for C3HN2O: C, 19.23; H,
0.54; N, 14.95%. Found: C, 19.19; H, 0.53; N, 14.96%.
Compound 4c: mp 140–141 °C. 1H NMR (300 MHz,
CDCl3): d = 6.37 (br, 1 H, NH), 7.35–7.56 (m, 3 H, ArH),
7.81 (d, 2 H, J = 7.26 Hz, ArH). 13C NMR (75 MHz, CDCl3):
d = 127.25, 128.48, 128.70, 131.87, 133.26, 169.87. IR
(diffuse reflectance): n = 3371 (m), 3181 (m), 2918 (m),
2220 (m, C≡N), 1657 (s, C=O), 1478 (m), 1392 (m), 1261
(m), 1195 (m), 1141 (s), 1119 (m), 807 (w), 789 (w) cm–1.
Compound 2i: 1H NMR (300 MHz, DMSO-d6): d = 5.79 (br,
1 H, NH), 6.93 (m, 1 H, ArH), 7.21–7.30 (m, 2 H, ArH), 7.36
(m, 1 H, ArH). 13C NMR (75 MHz, DMSO-d6): d = 107.39,
110.14, 120.35, 125.25, 130.32, 149.16, 150.52. IR (diffuse
reflectance): n = 3363 (m), 2964 (m), 2231 (m, C≡N), 1721
(s), 1598 (m), 1530 (s), 1348 (s), 1224 (s), 1071 (m), 886
(m), 799 (m), 736 (m), 673 (m) cm–1.
Compound 2j: mp 76–78 °C. 1H NMR (300 MHz, CDCl3):
d = 1.75 (s, 3 H, CH3), 4.74 (br, 1 H, NH), 6.87–6.96 (m, 2
Synlett 2006, No. 4, 559–562 © Thieme Stuttgart · New York