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CH2CH3), 22.5 (CH2CH2CH2CH2CH2CH3), 14.0 (CH2CH2-
CH2CH2CH2CH3) ppm; ES-MS: m=z (%) ¼ 375 (Mþ þ 1, 100).
cyclohexane=Et2O, 2=1–1.7=1): yield 116 mg (24%) as a
brown solid: mp 93–97ꢁC; Rf ¼ 0.40 (n-hexane=EtOAc,
1
1=1); H NMR (CDCl3): ꢁ ¼ 8.58 (2H, d, J ¼ 6.1 Hz, 300-
H), 7.53 (1H, t, J ¼ 1.3 Hz, 30-H), 7.41–7.40 (2H, m, 50-
H, 60-H), 7.31 (2H, d, J ¼ 6.1 Hz, 200-H), 2.80 (2H, t, J ¼
7.5 Hz, CH2CH2CH2CH2CH2CH2CH3), 1.81 (2H, p, J ¼
7.5 Hz, CH2CH2CH2CH2CH2CH2CH3), 1.27–1.20 (8H, m,
CH2CH2CH2CH2CH2CH2CH3), 0.84 (3H, br, t, J ¼ 6.4 Hz,
CH2CH2CH2CH2CH2CH2CH3) ppm; 13C NMR (CDCl3):
ꢁ ¼ 165.8 (3-C triazole), 153.0 (5-C triazole), 150.4 (300-C),
137.0 (100-C), 134.8, 134.5, 132.8 (10-C, 20-C, 40-C), 130.7
(60-C), 129.9 (30-C), 128.5 (50-C), 121.5 (200-C), 31.7
(CH2CH2CH2CH2CH2CH2CH3), 29.2 (CH2CH2CH2CH2-
CH2CH2CH3), 28.9 (CH2CH2CH2CH2CH2CH2CH3), 28.3
(CH2CH2CH2CH2CH2CH2CH3), 28.1 (CH2CH2CH2CH2-
CH2CH2CH3), 22.6 (CH2CH2CH2CH2CH2CH2CH3), 14.0
(CH2CH2CH2CH2CH2CH2CH3) ppm; ES-MS: m=z (%) ¼
389 (Mþ þ 1, 100).
5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-3-heptyl-1H-
1,2,4-triazole (15, C21H22Cl3N3)
Compound 15 was prepared from 250 mg 5 (0.78mmol),
0.113 cm3 4-chlorobenzylamine (0.93 mmol), 0.130 cm3 TEA
(0.93 mmol), and 10 cm3 aq. NaOCl (flash chromatography:
cyclohexane=CH2Cl2, 2.5=1–1=3 and medium pressure
flash chromatography: cyclohexane=Et2O, 8=1): yield 75mg
(23%) as a white solid: mp 56–58ꢁC; Rf ¼ 0.50 (n-hexane=
1
EtOAc, 5=1); H NMR (CDCl3): ꢁ ¼ 7.49 (1H, br, s, 30-H),
7.38–7.34 (2H, m, 50-H, 60-H), 7.36 (2H, d, J ¼ 8.7 Hz,
200-H), 7.26 (2H, d, J ¼ 8.6 Hz, 300-H), 2.78 (2H, t, J ¼
7.5 Hz, CH2CH2CH2CH2CH2CH2CH3), 1.80 (2H, p, J ¼
7.5 Hz, CH2CH2CH2CH2CH2CH2CH3), 1.33–1.24 (8H, m,
CH2CH2CH2CH2CH2CH2CH3), 0.83 (3H, br, t, J ¼ 6.3 Hz,
CH2CH2CH2CH2CH2CH2CH3) ppm; 13C NMR (CDCl3):
ꢁ ¼ 165.4 (3-C triazole), 154.5 (5-C triazole), 136.6 136.4
134.8, 132.8 (10-C, 20-C, 40-C, 400-C), 130.6 (60-C), 130.1
(30-C), 129.2, 129.0 (200-C, 300-C), 128.4 (50-C), 126.0 (100-C),
31.7 (CH2CH2CH2CH2CH2CH2CH3), 29.3 (CH2CH2CH2CH2-
CH2CH2CH3), 29.0 (CH2CH2CH2CH2CH2CH2CH3), 28.4
(CH2CH2CH2CH2CH2CH2CH3), 28.2 (CH2CH2CH2CH2-
CH2CH2CH3), 22.6 (CH2CH2CH2CH2CH2CH2CH3), 14.1
(CH2CH2CH2CH2CH2CH2CH3) ppm; ES-MS: m=z (%) ¼
422 (Mþ þ 1, 99).
5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-3-cyclohexyl-1H-
1,2,4-triazole (18, C20H18Cl3N3)
Compound 18 was prepared from 1.21 g 6 (4.0mmol),
0.580 cm3 4-chlorobenzylamine (4.8mmol), 0.660cm3 TEA
(4.8mmol), 15cm3 aq. NaOCl (recrystallized from MeCN):
yield 948 mg (59%) as a white solid: mp 118–120ꢁC; 1H
NMR (CDCl3): ꢁ ¼ 7.50 (1H, br, s, 30-H), 7.39–7.37 (4H, m,
50-H, 60-H, 2000-H), 7.27 (2H, d, J ¼ 8.6 Hz, 3000-H), 2.83 (1H, tt,
J ¼ 11.4, 3.4 Hz, 100-H cyclohexane), 2.14–2.09 (2H, m, 200-H
cyclohexane), 1.86–1.81 (2H, m, 300-H cyclohexane), 1.73–
1.67 (2H, m, 300-H cyclohexane), 1.49–1.23 (2H, m, 400-H cy-
clohexane) ppm; 13C NMR (CDCl3): ꢁ ¼ 169.1 (3-C triazole),
154.3 (5-C triazole), 136.5, 136.3, 134.9, 132.9 (10-C, 20-C, 40-
C, 4000-C), 130.6 (60-C), 130.1 (30-C), 129.2, 128.9 (2000-C, 3000-
C), 128.3 (50-C), 126.1 (1000-C), 37.7 (100-C), 31.8 (200-C), 26.0
(400-C), 25.9 (300-C). ES-MS: m=z (%) ¼ 406 (Mþ þ 1, 100).
1-(2,4-Dichlorophenyl)-5-(4-fluorophenyl)-3-heptyl-1H-
1,2,4-triazole (16, C21H22Cl2FN3)
Compound 16 was prepared from 200 mg 5 (0.62 mmol),
0.085 cm3 4-fluorobenzylamine (0.75 mmol), 0.104 cm3
TEA (0.75 mmol), 5 cm3 aq. NaOCl (flash chromatography:
cyclohexane=Et2O, 7=1): yield 88 mg (35%) as a brown
solid: mp 45–48ꢁC; Rf ¼ 0.30 (n-hexane=EtOAc, 5=1);
1H NMR (CDCl3): ꢁ ¼ 7.51–7.49 (1H, m, 30-H), 7.43
(2H, dd, J ¼ 8.5, 5.3 Hz, 200-H), 7.38–7.37 (2H, m, 50-H,
60-H), 6.99 (2H, t, J ¼ 8.5 Hz, 300-H), 2.79 (2H, t, J ¼
7.6 Hz, CH2CH2CH2CH2CH2CH2CH3), 1.82 (2H, p, J ¼
7.6 Hz, CH2CH2CH2CH2CH2CH2CH3), 1.71–1.26 (8H, m,
CH2CH2CH2CH2CH2CH2CH3), 0.85 (3H, br, t, J ¼ 6.4 Hz,
CH2CH2CH2CH2CH2CH2CH3) ppm; 13C NMR (CDCl3):
ꢁ ¼ 163.6 (1-C, d, JC-F ¼ 24 Hz, 400-C), 165.3 (3-C triazole),
154.7 (5-C triazole), 136.5, 134.9, 132.9 (10-C, 20-C, 40-
C), 130.6 (60-C), 130.2 (200-C), 130.0 (30-C), 128.3 (50-
C), 123.8 (100-C), 115.9 (1-C, d, JC-F ¼ 22Hz, 300-C), 31.7
(CH2CH2CH2CH2CH2CH2CH3), 29.3 (CH2CH2CH2CH2-
CH2CH2CH3), 29.0 (CH2CH2CH2CH2CH2CH2CH3), 28.4
(CH2CH2CH2CH2CH2CH2CH3), 28.2 (CH2CH2CH2CH2-
CH2CH2CH3), 22.6 (CH2CH2CH2CH2CH2CH2CH3), 14.1
(CH2CH2CH2CH2CH2CH2CH3) ppm; ES-MS: m=z (%) ¼
406 (Mþ þ 1, 100).
5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-3-[(2,6,6-
trimethyl-1-cyclohexene)-1-methyl]-1H-1,2,4-triazole
(19, C24H24Cl3N3)
Compound 19 was prepared from 215 mg 7 (0.6mmol),
0.087 cm3 4-chlorobenzylamine (0.7mmol), 0.100 cm3 TEA
(0.7mmol), 10 cm3 aq. NaOCl (medium pressure flash chro-
matography: cyclohexane=Et2O, 8=1): yield 94mg (34%) as
an orange oil; Rf ¼ 0.60 (cyclohexane=EtOAc, 5=1); 1H NMR
(CDCl3): ꢁ ¼ 7.49 (1H, t, J ¼ 1.3 Hz, 30-H), 7.37 (2H,
d, J ¼ 8.9 Hz, 200-H), 7.36–7.35 (2H, m, 50-H, 60-H), 7.27
(2H, d, J ¼ 8.9 Hz, 300-H), 3.75 (2H, s, CH2CCl), 2.00 (2H,
t, J ¼ 6.1 Hz, CH2C(CH3)¼), 1.71 (3H, s, CH2C(CH3)¼),
1.64–1.56 (2H, m, CH2CH2C(CH3)¼), 1.48–1.40 (2H, m,
CH2CH2C(CH3)2), 1.03 (6H, s, 2ÂCH3) ppm; 13C NMR
(CDCl3): ꢁ ¼ 165.1 (3-C triazole), 154.1 (5-C triazole),
136.4, 136.1, 135.0, 132.8 (10-C, 20-C, 40-C, 400-C), 133.1
(CH2C¼), 130.6 (60-C), 130.3 (CH3C¼), 130.2 (30-C),
129.2, 128.9 (200-C, 300-C), 128.3 (50-C), 126.2 (100-C), 39.6
(CH2C(CH3)2), 35.0 (C(CH3)2), 32.8 (CH2C(CH3)¼), 28.4
(2ÂCH3), 27.7 (CH2C¼), 20.6 (CH3), 19.4 (CH2) ppm; ES-
MS: m=z (%) ¼ 460 (Mþ þ 1, 95); HPLC: MeCN=H2O,
50=50, ꢂR % ¼ 6.55min (89%).
4-[1-(2,4-Dichlorophenyl)-3-heptyl-1H-1,2,4-triazole-5-yl]-
pyridine (17, C20H22Cl2N4)
Compound 17 was prepared from 400 mg 5 (1.2mmol),
0.152 cm3 4-(aminomethyl)pyridine (1.5 mmol), 0.207 cm3
TEA (1.5mmol), 7 cm3 aq. NaOCl (flash chromatography: