3878
S. H. Kwak et al.
Paper
Synthesis
HRMS (ESI): m/z [M + H]+ calcd for C15H14N3S: 268.0903; found:
5-(Methylsulfanyl)-1-(4-nitrophenyl)-3-phenyl-1,2,4-triazole (1g)
268.0910.
Pale yellow solid; yield: 59 mg (47%); mp 134–135 °C.
1H NMR (500 MHz, CDCl3): δ = 8.45–8.33 (m, 2 H), 8.16 (dd, J = 7.8, 1.6
Hz, 2 H), 8.05–7.91 (m, 2 H), 7.54–7.40 (m, 3 H), 2.86 (s, 3 H).
5-(Benzylsulfanyl)-1,3-diphenyl-1,2,4-triazole (1b)
Pale yellow oil; yield: 126 mg (92%).
1H NMR (500 MHz, CDCl3): δ = 8.24–8.16 (m, 2 H), 7.61–7.54 (m, 2 H),
13C NMR (126 MHz, CDCl3): δ = 162.57, 155.05, 146.39, 142.30,
129.99, 129.91, 128.67, 126.59, 124.96, 123.00, 16.14.
7.52–7.36 (m, 8 H), 7.35–7.22 (m, 3 H), 4.59 (s, 2 H).
HRMS (ESI): m/z [M + H]+ calcd for C15H13N4O2S: 313.0754; found:
313.0759.
13C NMR (126 MHz, CDCl3): δ = 183.59, 162.03, 152.85, 137.24,
136.51, 130.70, 129.62, 129.41, 129.26, 129.20, 128.66, 128.58,
128.51, 127.76, 126.43, 123.93, 37.98.
1-(4-Chlorophenyl)-5-(methylsulfanyl)-3-phenyl-1,2,4-triazole
(1h)
HRMS (ESI): m/z [M + H]+ calcd for C21H18N3S: 344.1216; found:
344.1218.
White solid; yield: 66 mg (55%); mp 117–119 °C.
1H NMR (500 MHz, CDCl3): δ = 8.15 (d, J = 7.1 Hz, 2 H), 7.61 (d, J = 8.4
Hz, 2 H), 7.55–7.36 (m, 5 H), 2.80 (s, 3 H).
5-(Isopropylsulfanyl)-1,3-diphenyl-1,2,4-triazole (1c)
Colorless oil; yield: 90 mg (76%).
13C NMR (126 MHz, DMSO-d6): δ = 161.13, 154.37, 135.49, 133.27,
129.98, 129.71, 129.64, 128.84, 125.95, 125.60, 15.57.
HRMS (ESI): m/z [M + H]+ calcd for C15H13ClN3S: 302.0513; found:
302.0520.
1H NMR (500 MHz, CDCl3): δ = 8.23–8.12 (m, 2 H), 7.68–7.60 (m, 2 H),
7.54–7.47 (m, 2 H), 7.47–7.36 (m, 4 H), 4.09 (hept, J = 6.8 Hz, 1 H),
1.47 (d, J = 6.8 Hz, 6 H).
13C NMR (126 MHz, CDCl3): δ = 162.18, 152.98, 137.42, 130.79,
129.32, 129.21, 128.52, 128.48, 126.42, 124.20, 39.60, 23.31.
HRMS (ESI): m/z [M + H]+ calcd for C17H18N3S: 296.1216; found:
5-(Methylsulfanyl)-3-phenyl-1-[3-(trifluoromethyl)phenyl]-1,2,4-
triazole (1i)
296.1219.
Pale yellow solid; yield: 78 mg (58%); mp 76–78 °C.
1H NMR (500 MHz, CDCl3): δ = 8.16 (dd, J = 8.1, 1.4 Hz, 2 H), 8.00 (s, 1
H), 7.89 (d, J = 7.6 Hz, 1 H), 7.71–7.60 (m, 2 H), 7.51–7.37 (m, 3 H),
2.82 (s, 3 H).
5-(Allylsulfanyl)-1,3-diphenyl-1,2,4-triazole (1d)
White solid; yield: 102 mg (87%); mp 61–62 °C.
1H NMR (500 MHz, CDCl3): δ = 8.22–8.10 (m, 2 H), 7.67–7.59 (m, 2 H),
7.54–7.48 (m, 2 H), 7.47–7.38 (m, 4 H), 6.01 (ddt, J = 17.1, 10.0, 7.1 Hz,
1 H), 5.34 (dd, J = 16.9, 1.3 Hz, 1 H), 5.16 (d, J = 10.0 Hz, 1 H), 3.99 (d,
J = 7.1 Hz, 2 H).
13C NMR (126 MHz, CDCl3): δ = 162.36, 154.44, 137.83, 131.98 (q,
J = 33.1 Hz), 130.31, 129.97, 129.63, 128.61, 126.49, 126.43, 124.87 (q,
J = 3.7 Hz), 123.45 (q, J = 272.6 Hz),120.54 (q, J = 3.9 Hz), 15.91.
HRMS (ESI): m/z [M + H]+ calcd for C16H13F3N3S: 336.0777; found:
336.0781.
13C NMR (126 MHz, CDCl3): δ = 162.07, 152.64, 137.30, 132.63,
130.68, 129.38, 129.30, 128.56, 128.55, 126.41, 124.02, 119.03, 36.38.
HRMS (ESI): m/z [M + H]+ calcd for C17H16N3S: 294.1059; found:
294.1066.
1-{3-[5-(Methylsulfanyl)-3-phenyl-1,2,4-triazol-1-yl]phenyl}eth-
anone (1j)
White solid; yield: 87 mg (70%); mp 115–117 °C.
1,3-Diphenyl-5-(prop-2-ynylsulfanyl)-1,2,4-triazole (1e)
1H NMR (500 MHz, CDCl3): δ = 8.27 (s, 1 H), 8.17 (d, J = 7.7 Hz, 2 H),
8.01 (d, J = 7.6 Hz, 1 H), 7.89 (d, J = 7.6 Hz, 1 H), 7.62 (t, J = 7.8 Hz, 1 H),
7.52–7.37 (m, 3 H), 2.82 (s, 3 H), 2.67 (s, 3 H).
13C NMR (126 MHz, CDCl3): δ = 196.73, 162.24, 154.32, 138.16,
137.76, 130.42, 129.72, 129.53, 128.58, 127.87, 127.79, 126.45,
123.27, 26.76, 15.89.
White solid; yield: 73 mg (63%); mp 124–125 °C.
1H NMR (500 MHz, CDCl3): δ = 8.16 (d, J = 7.1 Hz, 2 H), 7.63 (d, J = 7.7
Hz, 2 H), 7.52 (t, J = 7.7 Hz, 2 H), 7.49–7.38 (m, 4 H), 4.15 (d, J = 2.4 Hz,
2 H), 2.27 (t, J = 2.2 Hz, 1 H).
13C NMR (126 MHz, CDCl3): δ = 162.24, 151.49, 137.05, 130.47,
129.50, 129.42, 128.75, 128.57, 126.44, 123.90, 78.30, 72.25, 22.09.
HRMS (ESI): m/z [M + H]+ calcd for C17H16N3OS: 310.1009; found:
HRMS (ESI): m/z [M + H]+ calcd for C17H14N3S: 292.0903; found:
310.1014.
292.0904.
1-(2-Methoxyphenyl)-5-(methylsulfanyl)-3-phenyl-1,2,4-triazole
(1k)
3-[5-(Methylsulfanyl)-3-phenyl-1,2,4-triazol-1-yl]benzonitrile (1f)
Colorless oil; yield: 67 mg (56%).
White solid; yield: 94 mg (80%); mp 142–144 °C.
1H NMR (500 MHz, CDCl3): δ = 8.16 (d, J = 7.4 Hz, 2 H), 7.52–7.35 (m, 5
H), 7.13–7.01 (m, 2 H), 3.83 (s, 3 H), 2.71 (s, 3 H).
13C NMR (126 MHz, CDCl3): δ = 162.37, 156.23, 154.77, 131.49,
131.02, 129.31, 128.73, 128.61, 126.54, 125.77, 120.98, 112.43, 55.95,
15.90.
1H NMR (500 MHz, CDCl3): δ = 8.15 (dd, J = 7.9, 1.5 Hz, 2 H), 8.08–8.03
(m, 1 H), 7.97 (ddd, J = 8.0, 2.0, 1.1 Hz, 1 H), 7.70 (d, J = 7.8 Hz, 1 H),
7.64 (t, J = 7.9 Hz, 1 H), 7.51–7.41 (m, 3 H), 2.84 (s, 3 H).
13C NMR (126 MHz, CDCl3): δ = 162.47, 154.52, 138.15, 131.42,
130.34, 130.11, 129.77, 128.65, 127.27, 126.57, 126.50, 117.67,
113.68, 15.98.
HRMS (ESI): m/z [M + H]+ calcd for C16H16N3OS: 298.1009; found:
HRMS (ESI): m/z [M + H]+ calcd for C16H13N4S: 293.0855; found:
298.1013.
293.0862.
5-(Methylsulfanyl)-1-(o-tolyl)-3-phenyl-1,2,4-triazole (1l)
Pale yellow oil; yield: 87 mg (77%).
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2015, 47, 3874–3880