Sangshetti et al.
(4-chlorophenyl)(4-(4-(5-phenyl-4H-1,2,4-triazol-
3-yl)-1H-1,2,3-triazol-1-yl)piperidine-1-
yl)methanone (3g)
4-(4-(5-(4-methoxyphenyl)-4H-1,2,4-triazol-3-yl)-
1H-1,2,3-triazol-1-yl)-1-methylpiperidine (3k)
Off white solid; m.p. 201–203 ꢀC.
Yellowish solid; m.p. 174–175 ꢀC.
1H NMR (400 MHz, CDCl3): d = 7.90 (s, 1H), 7.70–7.42 (m, 4H),
7.30 (s, 1H), 4.90–4.80 (m, 1H), 4.35–4.30 (m, 2H), 3.24 (s, 3H),
3.12 (s, 3H), 2.90–2.88 (m, 2H), 2. 68–2.32 (m, 2H), 2.10–1.88 (m,
2H).
1H NMR (400 MHz, CDCl3): d = 8.15 (s, 1H), 7.85–7.36 (m, 9H), 7.29
(s, 1H), 4.82–4.73(m, 1H), 4.10–4.00 (m, 2H), 2.90–2.82 (m, 2H),
2.10–2.05 (m, 2H), 1.84–1.80 (m, 2H).
13C NMR (CDCl3) d = 27.1, 42.9, 59.7, 126.6,128.2, 128.7, 129.2,
13C NMR (CDCl3) d = 27.8, 48.2, 56.1, 115.4, 126.1, 129.1, 131.2,
130.0, 130.8, 131.7, 132.4, 136.8, 161.9, 165.6,172.0.
158.5, 162.1, 166.4.
ES-MS: m ⁄ z = 434[M+H]+.
ES-MS: m ⁄ z = 340[M+H]+.
4-(4-(5-(4-chlorophenyl)-4H-1,2,4-triazol-3-
yl)-1H-1,2,3-triazol-1-yl)-1-methylpiperidine
(3h)
1-ethyl-4-(4-(5-(4-methoxyphenyl)-4H-1,2,4-
triazol-3-yl)-1H-1,2,3-triazol-1-yl)piperidine (3l)
Off white solid; m.p. 201–203 ꢀC.
Yellowish solid; m.p. 224–226 ꢀC.
1H NMR (400 MHz, CDCl3): d = 8.10 (s, 1H), 7.80–7.42 (m, 4H), 7.35
(s, 1H), 4.90–4.85 (m, 1H), 4.45–4. 38 (q, 2H), 4.35–4.25 (m, 2H),
3.28 (s, 3H) 2.98–2.86 (m, 2H), 2.22–2.18 (m, 2H), 2.11–1.90 (m,
2H), 1.45–1.40 (t, 3H).
1H NMR (400 MHz, CDCl3): d = 8.10(s, 1H), 7. 80–7. 42 (m, 4H),
7.30 (s, 1H), 4.86–4.80 (m, 1H), 4.32–4.29 (m, 2H), 3.25 (s, 3H),
2.90–2.84 (m, 2H), 2. 60–2.32 (m, 2H), 2.10.1.90 (m, 2H).
13C NMR (CDCl3) d = 26.8, 46.2, 56.2, 62.3, 126.4, 127.2, 129.1,
13C NMR (CDCl3) d = 14.2, 28.2, 49.4, 56.3, 62.6, 116.2, 126.4,
129.9, 131.2, 132.8, 133.1, 133.8, 137.1,162.2, 164.8.
129.8, 132.1, 157.9, 160.8, 166.4.
ES-MS: m ⁄ z = 344 [M+H]+.
ES-MS: m ⁄ z = 354 [M+H]+.
1-(4-(4-(5-(4-chlorophenyl)-4H-1,2,4-triazol-3-yl)-
1H-1,2,3-triazol-1-yl)piperidine-1-yl)ethanone
(3i)
1-(methylsulfonyl)-4-(4-(5-(4-nitrophenyl)-4H-
1,2,4-triazol-3-yl)-1H-1,2,3-triazol-1-yl)piperidine
(3m)
White solid; m.p. 267–269 ꢀC.
Yellow solid; m.p. )189–190 ꢀC.
1H NMR (400 MHz, CDCl3): d = 7.95(s, 1H), 7.80–7.29 (m, 4H), 7.30
(s, 1H), 4.96–4.84 (m, 1H), 4.35–4.24 (m, 2H), 3.32(s, 3H), 2.92–2.88
(m, 2H), 2.64–2.32 (m, 2H), 2.12–1.85 (m, 2H). ES-MS: m ⁄ z = 372
[M+H]+.
1H NMR (400 MHz, CDCl3): d = 8.15 (s, 1H), 7 72–7. 38 (m, 4H),
7.37 (s, 1H), 4.89–4.81 (m, 1H), 4.32–4.28 (m, 2H), 3.24 (s, 3H),
2.92–2.86 (m, 2H), 2.69–2.32 (m, 2H), 2.10–1.85 (m, 2H).
13C NMR (CDCl3) d = 26.8, 40.4, 44.3, 61.6, 127.4, 129.4,
131.1,138.2, 157.6, 164.2
13C NMR (CDCl3) d = 23.2, 28.2, 44.4, 61.8, 128.2, 130.1, 131.1,
132.2, 133.8, 134.3, 161.2, 173.8.
ES-MS: m ⁄ z = 419 [M+H]+.
4-(4-(5-(4-chlorophenyl)-4H-1,2,4-triazol-3-yl)-1H-
1,2,3-triazol-1-yl)-1-(methylsulfonyl)piperidine
(3j)
1-(4-(4-(5-p-tolyl-4H-1,2,4-triazol-3-yl)-1H-1,2,3-
triazol-1-yl)piperidine-1-yl)ethanone (3n)
Off white solid; m.p. )201–202 ꢀC.
Off white solid; m.p. 201–203 ꢀC.
1H NMR (400 MHz, CDCl3): d = 8.19 (s, 1H), 7.75–7.40 (m, 4H), 7.30
(s, 1H), 4.90–4.82 (m, 1H), 4.30–4.28 (m, 2H), 3.20 (s, 3H),
2.90–2.86 (m, 2H), 2.69–2.35 (m, 2H), 2.11–1.87 (m, 2H).
1H NMR (400 MHz, CDCl3): d = 8.20 (s, 1H), 7.80–7.35 (m, 4H), 7.30
(s, 1H), 4.93–4.82 (m, 1H), 4.34–4.28 (m, 2H), 3.32 (s, 3H), 2.91–
2.87 (m, 2H), 2.87 (s, 3H), 2.65–2.35 (m, 2H), 2.10–1.90 (m, 2H).
13C NMR (CDCl3) d = 25.4, 42.7, 47.3, 60.4, 126.5, 129.6, 131.6,
13C NMR (CDCl3) d = 22.2,23.4, 26.6, 41.8, 62.1, 124.2, 129.1,
132.4, 132.9, 133.1, 161.2, 165.7.
131.1,132.5, 164.0
ES-MS: m ⁄ z = 409 [M+H]+.
ES-MS: m ⁄ z = 352 [M+H]+.
802
Chem Biol Drug Des 2011; 78: 800–809