3,5,6-Trisubstituted-1,2,4-triazines
267
2925, 2862, 1610, 1496, 1434, 822, 763; 1H NMR (CDCl3, 200 MHz) d 8.07–
8.02 (dd, J ¼ 5.77, 3.80 Hz, 1H), 7.61–7.56 (m, 5H), 7.47–7.42 (m, 2H),
7.23–7.14 (m, 4H), 2.41–2.37 (d, 6H); 13C NMR (CDCl3, 50 MHz) d
162.1, 154.9, 154.7, 141.1, 139.7, 134.8, 133.4, 132.7, 132.5, 132.0, 130.9,
130.7, 129.8, 129.3, 129.2, 129.1, 126.7, 21.2; C23H18ClN3 (371.5) calcd.
C, 74.29; H, 4.88; Cl, 9.53; N, 11.30; found C, 74.35; H, 4.81; Cl, 9.66; N,
11.19.
3-Phenyl-5,6-di(p-methoxyphenyl)-1,2,4-triazine (3m). Yellow amorphous
solid (86%), Rf 0.40 (ethyl acetate/petroleum ether: 20:80); mp 1658C; IR
(cm21) 3018, 2967, 2840, 1607, 1518, 1489, 1465, 1216, 835, 758; 1H
NMR (CDCl3, 200 MHz) d 8.67–8.62 (m, 2H) 7.73–7.53 (m, 7H), 6.95–
6.85 (m, 4H), 3.86–3.83 (dd, 6H); 13C NMR (CDCl3, 50 MHz) d 161.6,
160.5, 160.4, 154.6, 154.4, 134.9, 131.9, 131.1, 130.6, 128.6, 128.0, 113.9,
113.8, 55.2; C23H19N3O2 (369) calcd. C, 74.78; H, 5.18; N, 11.37; found C,
74.52; H, 5.37; N, 11.51.
3-(p-Tolyl)-5,6-di(p-methoxyphenyl)-1,2,4-triazine (3n). Yellow crystalline
solid (78%), Rf 0.40 (ethyl acetate/petroleum ether: 20:80); mp 1498C; IR
1
(cm21) 3006, 2935, 2838, 1607, 1577, 1518, 1488, 1460, 1215, 833, 755; H
NMR (CDCl3, 50 MHz) d 8.55–8.51 (d, J ¼ 8.17 Hz, 2H), 7.71–7.57 (m, 4H),
7.36–7.32 (d, J ¼ 8.17 Hz, 2H), 6.93–6.85 (m, 4H), 3.84–3.83 (d, 6H), 2.45
(s, 3H); 13C NMR (CDCl3, 200 MHz) d 161.4, 160.4, 154.2, 141.4, 132.1,
131.3, 130.5, 129.3, 128.0, 127.9, 113.8, 113.7, 55.0, 21.4; C24H21N3O2 (383)
calcd. C, 75.18; H, 5.52; N, 10.98; found C, 74.98; H, 5.67; N, 11.09.
3-Phenyl-5-methyl-6-ethyl-1,2,4-triazine (3o) and 3-Phenyl-5-ethyl-6-
methyl-1,2,4-triazine (3o0). 3o: white needle crystals, Rf 0.48 (ethyl acetate/
petroleum ether: 20:80); mp 1038C; IR (cm21) 2928, 2845, 1611, 1542,
1
1487, 742; H NMR (CDCl3, 200 MHz) d 8.54–8.49 (m, 2H), 7.53–7.49
(m, 3H), 3.08–2.79 (q, J ¼ 7.32 Hz, 2H), 2.61 (s, 3H), 1.47–1.40
(t, J ¼ 7.32 Hz, 3H); 13C NMR (CDCl3, 50 MHz) d 161.5, 159.2, 158.1,
135.0, 131.0, 130.9, 128.6, 127.8, 127.7, 25.9, 21.2, 11.6; C12H13N3 (199)
calcd. C, 72.33; H, 6.58; N, 21.09; found C, 72.66; H, 6.47; N, 20.91. 3o0:
faint orange crystalline solid, Rf 0.38 (ethyl acetate/petroleum ether:
1
20:80); mp 1228C; IR (cm21) 2947, 2855, 1610, 1598, 1478, 748; H NMR
(CDCl3, 200 MHz) d 8.56–8.51 (m, 2H), 7.53–7.49 (m, 3H), 2.91–2.80
(q, J ¼ 7.41 Hz, 2H), 2.71 (s, 3H), 1.44–1.37 (t, J ¼7.41 Hz, 3H); 13C
NMR (CDCl3, 50 MHz) d 161.9, 161.7, 155.1, 135.1, 130.8, 128.4, 127.7,
27.3, 18.8, 10.1; C12H13N3 (199) calcd. C, 72.33; H, 6.58; N, 21.09; found
C, 72.57; H, 6.33; N, 21.10.
3-Phenyl-5,6,7,8-tetrahydro-benzo[1,2,4]triazine (3p). Orange solid (61%), Rf
0.61 (ethyl acetate/petroleum ether: 20:80); mp 858C; IR (cm21) 3016, 2950,
2870, 1600, 1519, 1452, 1419, 1215, 756; H NMR (CDCl3, 200 MHz) d
1