Wang et al.
FULL PAPER
1
3
3
1
1
2
5
H), 2.30 (s, 3H); C NMR (101 MHz, CDCl
67.53, 162.65, 161.51, 157.16, 148.86, 148.04, 147.85,
46.71, 118.57, 112.53, 109.38, 68.84, 50.54, 43.52,
4.29, 11.07. Anal. calcd for C18
.57, N 28.12; found C 54.03, H 5.65, N 28.08.
3
) δ:
50.44, 43.51, 24.29. Anal. calcd for C18H F N OS: C
19 3 8
47.78, H 4.23, N 24.77; found C 47.53, H 4.23, N 24.40.
G7: The compound was obtained in 60.5% yield as
white crystals; m.p. 132-134 ℃. H NMR (400 MHz,
1
H
22
N
8
OS: C 54.25, H
3
CDCl ) δ: 10.21 (s, 1H), 7.71 (br s, 1H), 7.12 (d, J=3.2
G2: The compound was obtained in 65.2% yield as a
white solid; m.p. 146-147 ℃. H NMR (400 MHz,
Hz, 1H), 6.60 (br s, 1H), 6.24 (s, 1H), 5.27 (s, 2H),
1
3.88-3.87 (m, 4H), 2.88-2.87 (m, 4H), 2.26 (s, 6H);
1
3
CDCl
3
) δ: 10.37 (s, 1H), 7.66 (d, J=1.5 Hz, 1H), 7.03
d, J=3.4 Hz, 1H), 6.58 (dd, J=3.5, 1.7 Hz, 1H), 6.23
s, 1H), 5.15 (s, 2H), 3.93-3.78 (m, 4H), 2.93-2.78
C NMR (101 MHz, CDCl
150.65, 147.55, 147.39, 138.79 (q, J =42.42 Hz,
Triazole-C ), 119.55, 116.78 (q, J=272.7 Hz, CF ),
112.77, 109.04, 70.17, 50.50, 43.45, 24.06. Anal. calcd
OS: C 48.92, H 4.54, N 24.02; found C
3
) δ: 167.09, 165.11, 161.56,
(
(
(
3
3
1
3
m, 4H), 2.42 (s, 3H), 2.25 (s, 6H); C NMR (101 MHz,
) δ: 166.90, 162.58, 161.52, 148.75, 147.99,
47.74, 146.70, 118.54, 112.54, 108.79, 68.81, 50.57,
3.46, 24.05, 11.06. IR (KBr) v: 2939, 2877, 1569, 1502,
CDCl
3
21 3 8
for C19H F N
1
4
1
48.80, H 5.01, N 23.85.
G8: The compound was obtained in 64.1% yield as
−1
1
448, 1167 cm . Anal. calcd for C19
H N
24 8
OS: C 55.32,
white crystals; m.p. 140-142 ℃. H NMR (400 MHz,
H 5.86, N 27.16; found C 55.20, H 5.88, N 27.02.
CDCl ) δ: 10.50 (s, 1H), 8.28 (d, J=4.8 Hz, 2H), 7.63
3
G3: The compound was obtained in 68.5% yield as
yellow crystals; m.p. 147-149 ℃. H NMR (400 MHz,
(d, J=4.4 Hz, 1H), 7.59 (d, J=4.4 Hz, 1H), 7.17 (t, J=
1
4.4 Hz, 1H), 6.47 (t, J=4.8 Hz, 1H), 5.26 (s, 2H),
1
3
DMSO-d
d, J=4.8 Hz, 1H), 7.82 (d, J=2.8 Hz, 1H), 7.27 (dd,
J=4.9, 3.8 Hz, 1H), 6.48 (d, J=4.8 Hz, 1H), 5.09 (s,
6
) δ: 9.94 (s, 1H), 8.17 (d, J=4.8 Hz, 1H), 7.96
3.87-3.85 (m, 4H), 2.90-2.87 (m, 4H); C NMR
(
(101 MHz, CDCl ) δ: 165.20, 161.49, 157.74, 156.12,
3
138.77 (q, J=42.42 Hz, Triazole-C ), 136.41, 135.18,
3
2
3
1
1
2
5
H), 3.74-3.72 (m, 4H), 2.75-2.72 (m, 4H), 2.32 (s,
132.78, 128.15, 116.78 (q, J=273.7 Hz, CF ), 109.96,
3
1
3
H), 2.24 (s, 3H); C NMR (101 MHz, CDCl
3
) δ:
70.09, 50.36, 43.54. Anal. calcd for C H F N S : C
17
17
3
8 2
67.57, 162.72, 161.51, 157.17, 154.37, 147.78, 137.39,
34.25, 131.42, 128.02, 109.40, 68.85, 50.54, 43.53,
4.32, 11.02. Anal. calcd for C18H N S : C 52.15, H
22 8 2
4
4.92, H 3.77, N 24.65; found C 44.60, H 4.03, N 24.23.
G9: The compound was obtained in 62.7% yield as
1
white crystals; m.p. 129-131 ℃. H NMR (400 MHz,
.35, N 27.03; found C 52.11, H 5.20, N 26.98.
CDCl
3
) δ: 10.50 (s, 1H), 8.14 (d, J=4.8 Hz, 1H), 7.63
G4: The compound was obtained in 71.8% yield as
(
d, J=3.6 Hz, 1H), 7.59 (d, J=3.6 Hz, 1H), 7.16 (br s,
1
light yellow crystals; m.p. 143-145 ℃. H NMR (400
1
H), 6.36 (d, J=4.8 Hz, 1H), 5.27 (s, 2H), 3.87-3.85
1
3
MHz, DMSO-d
6
) δ: 9.95 (s, 1H), 7.96 (d, J=4.0 Hz,
H), 7.81 (s, 1H), 7.27 (d, J=3.3 Hz, 1H), 6.35 (s, 1H),
.09 (s, 2H), 3.73 (br s, 4H), 2.72 (br s, 4H), 2.31 (s,
(
(
1
1
1
m, 4H), 2.88-2.86 (m, 4H), 2.31 (s, 3H); C NMR
101 MHz, CDCl ) δ: 167.67, 165.19, 161.48, 157.21,
56.11, 138.75 (q, J=42.42 Hz, Triazole-C ), 136.43,
1
5
3
1
1
1
3
3
1
3
3
H), 2.19 (s, 6H); C NMR (101 MHz, CDCl ) δ:
35.15, 132.77, 128.14, 116.78 (q, J=272.7 Hz, CF
09.57, 70.13, 50.44, 43.50, 24.30. Anal. calcd for
: C 46.14, H 4.09, N 23.92; found C 45.88,
3
),
66.99, 162.76, 161.63, 154.31, 147.73, 137.44, 134.18,
31.38, 128.01, 108.83, 68.91, 50.65, 43.52, 24.06,
1.00. IR (KBr) v: 2913, 2843, 1600, 1575, 1496, 1157
18 19 3 8 2
C H F N S
H 4.47, N 23.92.
−
1
cm . Anal. calcd for C19
6.15; found C 53.17, H 5.48, N 25.94.
G5: The compound was obtained in 60.6% yield as
24 8 2
H N S : C 53.25, H 5.64, N
G10: The compound was obtained in 66.1% yield as
2
1
white crystals; m.p. 150-151 ℃. H NMR (400 MHz,
CDCl
3
) δ: 10.49 (s, 1H), 7.63 (d, J=3.6 Hz, 1H), 7.59
1
white crystals; m.p. 141-143 ℃. H NMR (400 MHz,
CDCl ) δ: 10.21 (s, 1H), 8.28 (d, J=4.7 Hz, 2H), 7.71
d, J=1.3 Hz, 1H), 7.12 (d, J=3.5 Hz, 1H), 6.60 (dd,
J=3.5, 1.7 Hz, 1H), 6.47 (t, J=4.7 Hz, 1H), 5.26 (s,
(
d, J=3.6 Hz, 1H), 7.17 (t, J=3.6 Hz, 1H), 6.24 (s, 1H),
3
5
6
1
1
.27 (s, 2H), 3.87 (br s, 4H), 2.88 (br s, 4H), 2.26 (s,
(
13
H); C NMR (101 MHz, CDCl
61.57, 156.10, 138.71 (q, J=42.42 Hz, Triazole-C
36.44, 135.15, 132.76, 128.14, 116.78 (q, J=272.7 Hz,
), 109.03, 70.17, 50.52, 43.47, 24.06. Anal. calcd for
: C 47.29, H 4.39, N 23.22; found C 47.65,
3
) δ: 167.09, 165.19,
3
),
13
2
H), 3.87-3.85 (m, 4H), 2.90-2.87 (m, 4H);
C
NMR (101 MHz, CDCl
50.65, 147.54, 147.43, 139.52 (m, Triazole-C
16.79 (q, J=272.7 Hz, CF
3
) δ: 165.15, 161.52, 157.73,
), 119.46,
), 112.76, 109.96, 70.12,
0.37, 43.55. Anal. calcd for C17 OS: C 46.57, H
CF
3
1
1
5
3
3
19 21 3 8 2
C H F N S
3
H 4.05, N 22.95.
17 3 8
H F N
.91, N 25.56; found C 46.67, H 4.05, N 25.23.
General synthetic procedures for 1-[(4-phenyl/(py-
ridin-2-yl)piperazin-1-yl)methyl]-4-(furan/thiophen-
G6: The compound was obtained in 69.2% yield as
1
2
1
-ylmethylene)amino-3-methyl/trifluoro-methyl-1H-
,2,4-triazole-5(4H)-thione H
white crystals; m.p. 126-128 ℃. H NMR (400 MHz,
CDCl
3
) δ: 10.21 (s, 1H), 8.14 (d, J=4.8 Hz, 1H), 7.70 (s,
H), 7.12 (d, J=3.2 Hz, 1H), 6.61 (bs, 1H), 6.36 (d, J=
.8 Hz, 1H), 5.27 (s, 2H), 3.87-3.86 (m, 4H), 2.88-
1
4
2
It was similar with that of F using 4-phenyl-pipera-
zine or 4-(pyridine-2-yl)piperazine as amine material
(Scheme 2).
13
3
.87 (m, 4H), 2.31 (s, 3H); C NMR (101 MHz, CDCl )
δ: 167.66, 165.14, 161.49, 157.20, 150.65, 147.54,
H1: The compound was obtained in 83.5% yield as
1
1
1
47.42, 138.83 (q, J=42.42 Hz, Triazole-C
3
), 119.47,
colorless crystals; m.p. 110-111 ℃. H NMR (400
16.79 (q, J=272.7 Hz, CF ), 112.76, 109.57, 70.15,
3
MHz, CDCl ) δ: 10.40 (s, 1H), 7.69 (d, J=1.5 Hz, 1H),
3
1128
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Chin. J. Chem. 2015, 33, 1124—1134