Y.-G. Wang et al. / Tetrahedron 63 (2007) 7866–7873
7869
Anal. Calcd for C24H23N3Se: C, 66.66%; H, 5.36%; N,
9.72%; Found: C, 66.73%; H, 5.33%; N, 9.81%.
C18H19N3Se: C, 60.67%; H, 5.37%; N, 11.79%; Found: C,
60.60%; H, 5.41%; N, 11.86%.
4.1.4.6. 3-Benzyl-4-phenyl-5-(2-phenylselanyl-ethyl)-
4H-[1,2,4]triazole (5f). Oil. 1H NMR (CDCl3) d 7.46–
7.44 (1H, m), 7.37–7.33 (2H, m), 7.27–7.26 (2H, m),
7.15–7.11 (6H, m), 6.89–6.83 (4H, m), 3.97 (2H, s), 3.13–
3.09 (2H, m), 2.92–2.89 (2H, m); 13C NMR (CDCl3)
d 154.0, 153.5, 135.3, 133.0, 132.2, 129.6, 129.5, 128.9,
128.8, 128.3, 128.1, 127.0, 126.7, 126.5, 31.3, 26.2, 23.6;
MS m/z 338 (100), 419 (M+); IR nmax (cmꢂ1) 3058, 2929,
1599, 1499, 1478, 1436, 733, 694; Anal. Calcd for
C23H21N3Se: C, 66.03%; H, 5.06%; N, 10.04%; Found: C,
65.90%; H, 5.20%; N, 10.09%.
4.1.4.11. 3-Methyl-4-naphthalen-1-yl-5-(2-phenylse-
lanyl-ethyl)-4H-[1,2,4]triazole (5k). Oil. 1H NMR
(CDCl3) d 8.06–7.99 (2H, m), 7.61–7.53 (3H, m), 7.32–
7.30 (1H, d), 7.17–7.06 (6H, m), 3.09–3.02 (2H, m), 2.86–
2.82 (2H, m), 2.16 (3H, s); 13C NMR (CDCl3) d 154.6,
152.4, 134.3, 132.3, 130.6, 129.8, 129.6, 129.0, 128.9,
128.7, 128.4, 127.4, 126.8, 125.6, 125.4, 121.3, 26.4, 23.8,
10.7; MS m/z 312 (100), 393 (M+); IR nmax (cmꢂ1) 3057,
2929, 1520, 1473, 1426, 865, 779, 739; Anal. Calcd for
C21H19N3Se: C, 64.28%; H, 4.88%; N, 10.71%; Found: C,
64.36%; H, 4.79%; N, 10.78%.
4.1.4.7. 3-(4-Methoxy-phenyl)-5-(2-phenylselanyl-eth-
yl)-4-p-tolyl-4H-[1,2,4]triazole (5g). White solid, mp
4.1.4.12. 4-(3-Methoxy-phenyl)-3-methyl-5-(2-phenyl-
selanyl-ethyl)-4H-[1,2,4]triazole (5l). Oil. 1H NMR
(CDCl3) d 7.43–7.39 (1H, m), 7.33–7.31 (2H, m), 7.19–
7.17 (3H, m), 7.07–7.04 (1H, m), 6.72–6.70 (1H, m),
6.66–6.65 (1H, m), 3.81 (3H, s), 3.16–3.12 (2H, m), 3.00–
2.96 (2H, m), 2.26 (3H, s); 13C NMR (CDCl3) d 160.5,
153.6, 151.5, 134.5, 132.4, 130.7, 129.1, 128.9, 126.8,
118.8, 115.1, 112.6, 55.4, 26.4, 23.8, 10.9; MS m/z 292
(100), 373 (M+); IR nmax (cmꢂ1) 3059, 2935, 1601, 1492,
1424, 1226, 1026, 740, 693; Anal. Calcd for C18H19N3OSe:
C, 58.07%; H, 5.14%; N, 11.29%; Found: C, 58.18%; H,
5.23%; N, 11.20%.
1
86–88 ꢀC. H NMR (CDCl3) d 7.32 (2H, d, J¼8.8 Hz),
7.30–7.28 (2H, m), 7.21 (2H, d, J¼8.0 Hz), 7.17–7.14
(3H, m), 6.98 (2H, d, J¼8.0 Hz), 6.74 (2H, d, J¼8.8 Hz),
3.68 (3H, s), 3.15–3.11 (2H, m), 3.02–2.98 (2H, m), 2.39
(3H, s); 13C NMR (CDCl3) d 159.9, 154.1, 153.2, 139.3,
132.0, 131.2, 130.2, 129.1, 128.7, 128.5, 126.5, 126.4,
118.6, 113.3, 54.6, 26.1, 23.4, 20.7; MS m/z 368 (100),
449 (M+); IR nmax (cmꢂ1) 3055, 2936, 1613, 1578, 1514,
1476, 1253, 1178, 1029, 835, 738; Anal. Calcd for
C24H23N3OSe: C, 64.28%; H, 5.17%; N, 9.37%; Found: C,
64.19%; H, 5.28%; N, 9.41%.
4.1.4.13.
3-Isopropyl-4-phenyl-5-(2-phenylselanyl-
4.1.4.8. 3-(4-Methoxy-phenyl)-5-(2-phenylselanyl-eth-
yl)-4-o-tolyl-4H-[1,2,4]triazole (5h). Oil. 1H NMR
(CDCl3) d 7.45–7.41 (1H, m), 7.35 (2H, d, J¼8.8 Hz),
7.30–7.28 (4H, m), 7.18–7.15 (4H, m), 6.76 (2H, d,
J¼8.8 Hz), 3.72 (3H, s), 3.17–3.15 (2H, m), 2.93–2.91
(2H, m), 1.83 (3H, s); 13C NMR (CDCl3) d 160.3, 154.1,
153.2, 135.2, 133.2, 132.1, 131.6, 130.0, 129.1, 128.8,
128.6, 127.7, 127.5, 126.7, 119.1, 113.7, 54.9, 26.2, 23.4,
17.1; MS m/z 368 (100), 449 (M+); IR nmax (cmꢂ1) 3056,
2937, 1612, 1471, 1254, 1180, 1028, 838, 737; Anal. Calcd
for C24H23N3OSe: C, 64.28%; H, 5.17%; N, 9.37%; Found:
C, 64.22%; H, 5.24%; N, 9.49%.
ethyl)-4H-[1,2,4]triazole (5m). Oil. 1H NMR (CDCl3)
d 7.53–7.51 (3H, m), 7.28–7.26 (2H, m), 7.17–7.13 (5H, m),
3.13–3.09 (2H, m), 2.96–2.92 (2H, m), 2.81–2.74 (1H, m),
1.24–1.23 (6H, m); 13C NMR (CDCl3) d 159.2, 153.3,
133.3, 132.2, 132.0, 129.8, 129.6, 128.7, 126.9, 126.6, 26.1,
24.8, 23.6, 20.8; MS m/z 290 (100), 371 (M+); IR nmax
(cmꢂ1) 3054, 2971, 2931, 1578, 1500, 1436, 774, 738,
693; Anal. Calcd for C19H21N3Se: C, 61.62%; H, 5.72%;
N, 11.35%; Found: C, 61.51%; H, 5.81%; N, 11.40%.
4.1.4.14. 3-Isopropyl-5-(2-phenylselanyl-ethyl)-4-p-
tolyl-4H-[1,2,4]triazole (5n). Oil. 1H NMR (CDCl3)
d 7.30 (2H, d, J¼8.0 Hz), 7.28–7.26 (2H, m), 7.19–7.15
(3H, m), 7.02 (2H, d, J¼8.0 Hz), 3.12–3.08 (2H, m), 2.96–
2.92 (2H, m), 2.81–2.74 (1H, m), 2.45 (3H, s), 1.24 (3H,
s), 1.23 (3H, s); 13C NMR (CDCl3) d 159.3, 153.4, 139.8,
132.1, 130.6, 130.3, 128.9, 128.7, 126.7, 126.5, 26.1, 24.8,
23.6, 20.9, 20.8; MS m/z 304 (100), 385 (M+); IR nmax
(cmꢂ1) 3052, 2972, 2930, 1578, 1515, 1434, 829, 738;
Anal. Calcd for C20H23N3Se: C, 62.49%; H, 6.03%; N,
10.93%; Found: C, 62.40%; H, 6.07%; N, 10.98%.
4.1.4.9. 4-(4-Chloro-phenyl)-3-(4-methoxy-phenyl)-5-
(2-phenylselanyl-ethyl)-4H-[1,2,4]triazole (5i). Low point
solid. 1H NMR (CDCl3) d 7.38 (2H, d, J¼8.4 Hz), 7.30–7.28
(2H, m), 7.25 (2H, d, J¼8.8 Hz), 7.23–7.18 (3H, m), 7.05
(2H, d, J¼8.4 Hz), 6.76 (2H, d, J¼8.8 Hz), 3.72 (3H, s),
3.13–3.09 (2H, m), 2.99–2.95 (2H, m); 13C NMR (CDCl3)
d 160.3, 154.1, 153.4, 135.4, 132.5, 132.4, 130.0, 129.4,
128.8, 128.7, 128.4, 126.9, 118.2, 113.7, 54.9, 26.2, 23.7;
MS m/z 311 (100), 469 (M+); IR nmax (cmꢂ1) 3055, 2937,
1678, 1612, 1499, 1254, 1180, 1028, 839, 738; Anal. Calcd
for C23H20ClN3OSe: C, 58.92%; H, 4.30%; N, 8.96%;
Found: C, 59.0%; H, 4.35%; N, 9.04%.
4.1.4.15. 3-Isopropyl-5-(2-phenylselanyl-ethyl)-4-o-
tolyl-4H-[1,2,4]triazole (5o). Oil. 1H NMR (CDCl3)
d 7.48–7.44 (1H, m), 7.38–7.34 (2H, m), 7.28–7.25 (2H,
m), 7.19–7.16 (3H, m), 7.08–7.06 (1H, m), 3.14–3.10
(2H, m), 2.95–2.89 (1H, m), 2.77–2.73 (1H, m), 2.63–2.59
(1H, m), 1.94 (3H, s), 1.27–1.21 (6H, m); 13C NMR
(CDCl3) d 159.2, 153.2, 135.2, 132.3, 132.1, 131.5, 130.1,
129.0, 128.9, 127.8, 127.3, 126.7, 26.2, 25.1, 23.4, 21.4,
4.1.4.10. 3-Methyl-5-(2-phenylselanyl-ethyl)-4-p-tolyl-
4H-[1,2,4]triazole (5j). White solid, mp 87–89 ꢀC. 1H NMR
(CDCl3) d 7.16–7.14 (4H, m), 7.04–7.02 (3H, m), 6.87–6.85
(2H, m), 2.99–2.95 (2H, m), 2.84–2.80 (2H, m), 2.30 (3H, s),
2.08 (3H, s); 13C NMR (CDCl3) d 153.3, 151.2, 139.6, 132.1,
130.5, 130.2, 128.8, 128.5, 126.5, 126.1, 26.0, 23.5, 20.7,
10.6; MS m/z 276 (100), 357 (M+); IR nmax (cmꢂ1) 3052,
2930, 1582, 1518, 1435, 802, 695; Anal. Calcd for
20.5, 16.9; MS m/z 304 (100), 385 (M+); IR nmax (cmꢂ1
)
3053, 2971, 2930, 1578, 1505, 1468, 1433, 774, 737;
Anal. Calcd for C20H23N3Se: C, 62.49%; H, 6.03%; N,
10.93%; Found: 62.38%; H, 6.12%; N, 11.00%.