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J. DONG ET AL.
IR (KBr) n ¼ 3061, 2978, 2931, 1608, 1542, 1321, 1246, 1177, 842, 742 cmꢃ1. Anal.
calcd. for C19H18N2O: C, 78.59; H, 6.25; N, 9.65; Found: C, 78.57; H, 6.43; N, 9.81.
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Compound 4d. Mp 191–192 ꢀC. H NMR (CDCl3) d ¼ 2.96 (t, J ¼ 8.3 Hz,
2H), 3.82 (s, 3H), 4.02 (t, J ¼ 8.3 Hz, 2H), 6.97–7.04 (m, 1H), 7.16 (t, J ¼ 7.4 Hz,
1H), 7.30–7.21 (m, 3H), 7.42–7.30 (m, 2H), 7.64 (d, J ¼ 8.0 Hz, 1H), 8.41 (s, 1H).
13C NMR (CDCl3) d ¼ 159.95, 159.38, 138.86, 136.61, 129.77, 127.81, 125.51,
124.57, 120.36, 120.31, 120.00, 117.83, 116.15, 112.85, 112.10, 55.41, 48.75, 19.26.
MS m=z (%) 276 (Mþ, 87), 275 (100), 260 (5), 245 (7), 232 (7), 217 (10), 204 (11),
143 (3), 115 (4), 102 (2), 77 (1). IR (KBr) n ¼ 3060, 2940, 2830, 1579, 1542, 1321,
1288, 1215, 1055, 1018, 750 cmꢃ1. Anal. calcd. for C18H16N2O: C, 78.24; H, 5.84;
N, 10.14; Found: C, 78.14; H, 5.93; N, 10.06.
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Compound 4e. Mp 167–168 ꢀC. H NMR (CDCl3) d ¼ 2.97 (t, J ¼ 8.5 Hz,
2H), 3.85 (s, 3H), 4.10 (t, J ¼ 8.5 Hz, 2H), 7.05 (d, J ¼ 8.3 Hz, 1H), 7.08 (dd,
J1 ¼ 7.4 Hz, J2 ¼ 7.5 Hz, 1H), 7.14 (dd, J1 ¼ 7.1 Hz, J2 ¼ 7.2 Hz, 1H), 7.24 (d,
J ¼ 8.1 Hz, 1H), 7.32 (d, J ¼ 8.2 Hz, 1H), 7.44 (dd, J1 ¼ 8.2 Hz, J2 ¼ 8.3 Hz, 1H),
7.48 (dd, J1 ¼ 7.5 Hz, J2 ¼ 1.6 Hz, 1H), 7.62 (d, J ¼ 8.0 Hz, 1H), 8.30 (s, 1H). 13C
NMR (CDCl3) d ¼ 158.84, 156.70, 136.57, 130.93, 130.56, 129.34, 127.73, 125.53,
124.42, 121.69, 120.13, 120.03, 116.68, 111.92, 111.77, 56.19, 49.02, 19.28. MS m=z
(%) 276 (Mþ, 100), 259 (45), 247 (60), 232 (11), 218 (23), 204 (13), 171 (5), 143
(5), 115 (4), 102 (2). IR (KBr) n ¼ 2938, 2837, 1600, 1543, 1491, 1464, 1320, 1300,
1246, 1012, 747 cmꢃ1. Anal. calcd. for C18H16N2O: C, 78.24; H, 5.84; N, 10.14;
Found: C, 77.91; H, 5.85; N, 10.13.
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Compound 4f. Mp 123–124 ꢀC. H NMR (CDCl3) d ¼ 1.25 (t, J ¼ 7.0 Hz,
3H), 2.96 (t, J ¼ 8.5 Hz, 2H), 4.09 (t, J ¼ 8.5 Hz, 2H), 4.13 (q, J ¼ 7.0 Hz, 2H), 7.04
(d, J ¼ 8.2 Hz, 1H), 7.07 (dd, J1 ¼ 7.4 Hz, J2 ¼ 7.5 Hz, 1H), 7.14 (dd, J1 ¼ 7.1 Hz,
J2 ¼ 7.2 Hz, 1H), 7.22–7.24 (m, 1H), 7.32 (d, J ¼ 8.2 Hz, 1H), 7.42 (dd, J1 ¼ 8.2 Hz,
J2 ¼ 8.3 Hz, 1H), 7.52 (dd, J1 ¼ 7.5 Hz, J2 ¼ 1.6 Hz, 1H), 7.63 (d, J ¼ 8.0 Hz, 1H),
8.53 (s, 1H). 13C NMR (CDCl3) d ¼ 159.16, 155.96, 136.61, 130.92, 130.71, 129.55,
128.33, 125.44, 124.34, 121.81, 120.03, 120.00, 116.68, 113.24, 111.89, 64.90, 48.95,
19.33, 14.81. MS m=z (%) 290 (Mþ, 57), 275 (100), 261 (22), 245 (47), 233 (7), 217
(13), 144 (6), 115 (3), 102 (1). HRMS calcd. for C19H18N2O: 290.1419; found:
290.1420. IR (KBr) n ¼ 3060, 2980, 2943, 2891, 1601, 1538, 1493, 1453, 1319,
1306, 1244, 1154, 1123, 1042, 744 cmꢃ1
.
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Compound 4g. Mp 192–193 ꢀC. H NMR (CDCl3) d ¼ 2.99 (t, J ¼ 8.6 Hz,
2H), 4.06 (t, J ¼ 8.6 Hz, 2H), 7.09–7.17 (m, 1H), 7.19–7.28 (m, 2H), 7.30–7.43 (m,
3H), 7.45 (dd, J ¼ 7.8 Hz, J2 ¼ 1.4 Hz, 1H), 7.62 (d, J ¼ 8.0 Hz, 1H), 8.30 (s, 1H).
1
13C NMR (CDCl3) d ¼ 158.82, 137.00, 136.76, 132.38, 130.56, 130.41, 130.00,
128.34, 127.27, 125.43, 124.65, 120.29, 120.08, 116.86, 112.16, 48.96, 19.32. MS m=z
(%) 280 (Mþ, 69), 279 (100), 243 (12), 217 (33), 189 (3), 143 (4), 122 (5), 115 (4), 89
(2). IR (KBr) n ¼ 2942, 2875, 1590, 1543, 1433, 1320, 1294, 1062, 750 cmꢃ1. Anal.
calcd. for C17H13ClN2 (%): C, 72.73; H, 4.67; N, 9.98; Found: C, 72.81; H, 4.63;
N, 9.89.
Compound 4h. Mp 289–290 ꢀC (lit.[2a] 288–290 ꢀC). 1H NMR (CDCl3)
d ¼ 2.99 (t, J ¼ 8.3 Hz, 2H), 3.95 (s, 3H), 3.96 (s, 3H), 4.03 (t, J ¼ 8.3 Hz, 2H), 6.96