Med Chem Res
0
0
000
000
2
.46 (s, 3H, 3-CH ), 3.01 (s, 3H, 5-CH ), 7.00–7.04 (m,
3
7.79–7.84 (m, 4H, 2 , 6 , 2 , 6 -H); Anal. calcd for
C H ClN S (%): C, 61.07; H, 4.07; N, 17.79. Found (%):
3
0
00
000
00
0
0
3
H, 3 , 5 -H), 7.05 (s, 1H, 5 -H), 7.17 (d, 2H, 3 , 5 -H,
3
2
0
16
5
3
0
0
JH-H = 8.24 Hz), 7.63 (d, 2H, 2 , 6 -H, J
= 7.96 Hz),
C, 61.04; H, 4.08; N, 17.75.
H-H
000 000
.74–7.77 (m, 2H, 2 , 6 -H); Anal. calcd for C H FN S
21 18 5
7
00
(
E)-2 -(3,5-Dimethyl-4-(phenyldiazenyl)-1H-pyrazol-1-yl)-
(
%): C, 64.45; H, 4.60; N, 17.90. Found (%): C, 64.44; H,
.56; N, 17.88.
0
0
000
4
1
-(4 -fluorophenyl)thiazole 3j Yield: 83 %; m.p.
-
64–165 °C; IR (mmax, cm ): 1697 (C=N str.), 1566 (C=C
4
1
0
0
1
(
E)-2 -(3,5-Dimethyl-4-(p-tolyldiazenyl)-1H-pyrazol-1-yl)-
0
str.); H NMR (400 MHz; CDCl , d ): 2.54 (s, 3H,
3
H
0
000 000
3-CH ), 3.11 (s, 3H, 5-CH ), 7.07–7.12 (m, 2H, 3 , 5 -
3 3
4
-p-tolylthiazole 3e Yield: 84 %; m.p. 187–189 °C; IR
-
1
1
0
0
0
(
mmax, cm ): 1698 (C=N str.), 1565 (C=C str.); H NMR
H), 7.13 (s, 1H, 5 -H), 7.37–7.41 (m, 1H, 4 -H), 7.45–7.48
00
0
00
0
0
0
0
000
000
(
400 MHz; CDCl , d ): 2.40 (s, 3H, 4 -CH ), 2.43 (s, 3H,
(m, 2H, 3 , 5 -H), 7.80–7.85 (m, 2 , 6 , 4 , 2 , 6 -H);
Anal. calcd for C H FN S (%): C, 63.66; H, 4.24; N,
3
H
3
0
4
-CH ), 2.58 (s, 3H, 3-CH ), 3.16 (s, 3H, 5-CH ), 7.21 (s,
3
3
3
20 16
5
0
0
000
000
3
1
H, 5 -H), 7.25 (d, 2H, 3 , 5 -H, J
= 8.12 Hz), 7.29
18.57. Found (%): C, 63.61; H, 4.22; N, 18.55.
H-H
0
0
3
d, 2H, 3 , 5 -H, J
0 0
= 8.20 Hz), 7.75 (d, 2H, 2 , 6 -H,
H-H
(
00
(
E)-2 -(3,5-Dimethyl-4-(phenyldiazenyl)-1H-pyrazol-1-yl)-
00
3
000
000
3
JH-H = 8.20 Hz), 7.81(d, 2H, 2 , 6 -H,
JH-H
4
-p-tolylthiazole 3k Yield: 87 %; m.p. 167 °C; IR (mmax,
=
8.12 Hz); Anal. calcd for C H N S (%): C, 68.22; H,
2
2
21
5
-1 1
cm ): 1698 (C=N str.), 1568 (C=C str.); H NMR
5
.43; N, 18.09. Found (%): C, 68.20; H, 5.41; N, 18.07.
000
400 MHz; CDCl , d ): 2.27 (s, 3H, 4 -CH ), 2.46 (s, 3H,
3
(
3
H
0
0
00
00
2
-(3,5-Dimethyl-4-(p-tolyldiazenyl)-1H-pyrazol-1-yl)-4 -
0
3-CH ), 3.03 (s, 3H, 5-CH ), 7.05 (s, 1H, 5 -H), 7.12 (d,
3
000
3
00
000
3
0
= 8.00 Hz), 7.28–7.31 (m, 1H, 4 -H),
H-H
(
naphthalen-2 -yl)thiazole 3f Yield: 78 %; m.p.
-
2H, 3 , 5 -H, J
1
0 0 000 000
7.35–7.39 (m, 2H, 3 , 5 -H), 7.67 (d, 2H, 2 , 6 -H, J
H-H
3
1
76–179 °C; IR (mmax, cm ): 1696 (C=N str.), 1566 (C=C
1
0
0
0
3
str.); H NMR (400 MHz; CDCl , d ): 2.40 (s, 3H, 4 -
= 8.00 Hz), 7.72 (d, 2H, 2 , 6 -H, J = 7.56 Hz); Anal.
H-H
3
H
CH ), 2.55 (s, 3H, 3-CH ), 3.15 (s, 3H, 5-CH ), 7.26 (d,
3
calcd for C H N S (%): C, 67.56; H, 5.09; N, 18.77.
21 19 5
3
3
0
0
3
H, 3 , 5 -H, JH-H = 7.80 Hz), 7.31 (s, 1H, 5 -H),
00
2
7
2
Found (%): C, 67.55; H, 5.03; N, 18.72.
0
00
000
000
000
000 000
.45–7.97 (m, 6H, 3 , 4 , 5 , 6 , 7 , 8 -H), 7.73 (d, 2H,
0
0
0
00
2
-(3,5-Dimethyl-4-(phenyldiazenyl)-1H-pyrazol-1-yl)-4 -
000
0
3
, 6 -H, J
000
= 7.80 Hz), 8.34 (s, 1H, 1 -H); Anal. calcd
H-H
(
naphthalen-2 -yl)thiazole 3l Yield: 80 %; m.p.
-1
80–181 °C; IR (mmax, cm ): 1698 (C=N str.), 1567 (C=C
str.); H NMR (400 MHz; CDCl , d ): 2.59 (s, 3H,
00
3-CH ), 3.21 (s, 3H, 5-CH ), 7.37 (s, 1H, 5 -H), 7.40–7.44
3 3
for C H N S (%): C, 70.92; H, 4.96; N, 16.55. Found
2
5
21
5
1
(
%): C, 70.90; H, 4.92; N, 16.52.
1
3
H
0
0
(
E)-2 -(3,5-Dimethyl-4-(phenyldiazenyl)-1H-pyrazol-1-yl)-
0
0
0 0 0 0 0 000 000 000
4
-phenylthiazole 3g Yield: 80 %; m.p. 168–170 °C; IR
(m, 1H, 4 -H), 7.48–7.98 (m, 10H, 2 , 3 , 5 , 6 , 3 , 4 , 5 ,
000
-
1
1
000
000
000
(
mmax, cm ): 1694 (C=N str.), 1564 (C=C str.); H NMR
6 , 7 , 8 -H), 8.39 (s, 1H, 1 -H); Anal. calcd for
C H N S (%): C, 70.42; H, 4.65; N, 17.11. Found (%): C,
(
400 MHz; CDCl , d ): 2.57 (s, 3H, 3-CH ), 3.15 (s, 3H,
-CH ), 7.23 (s, 1H, 5 -H), 7.32–7.36 (m, 1H, 4 -H),
3
3
H
3
24 19 5
00
000
5
7
70.39; H, 4.62; N, 17.07.
0
0
0
000
000
0
3
0
.38–7.49 (m, 5H, 3 , 5 , 4 , 3 , 5 -H), 7.83 (d, 2H, 2 , 6 -
3
0
0
0
(
E)-2 -(4-((4 -Fluorophenyl)diazenyl)-3,5-dimethyl-1H-
00
000
000
H, JH-H = 7.52 Hz), 7.89 (d, 2H, 2 , 6 -H, JH-H
7.40 Hz); Anal. calcd for C H N S (%): C, 66.85; H,
pyrazol-1-yl)-4 -phenylthiazole 3m Yield: 82 %; m.p.
-1
94 °C; IR (mmax, cm ): 1696 (C=N str.), 1562 (C=C str.);
H NMR (400 MHz; CDCl , d ): 2.56 (s, 3H, 3-CH ), 3.15
0 0
(s, 3H, 5-CH ), 7.14–7.19 (m, 2H, 3 , 5 -H), 7.27 (s, 1H,
3
=
2
0
17
5
1
1
4
.74; N, 19.50. Found (%): C, 66.80; H, 4.70; N, 19.48.
3
H
3
0
0
000
00
(
E)-4 -(4 -Bromophenyl)-2 -(3,5-dimethyl-4-(phenyl-
0
0
000
000
diazenyl)-1H-pyrazol-1-yl)thiazole 3h Yield: 84 %;
1
5 -H), 7.34–7.37 (m, 1H, 4 -H), 7.43–7.47 (m, 2H, 3 ,
0
-
000
0
000
m.p. 200–201 °C; IR (mmax, cm ): 1698 (C=N str.), 1569
5 -H), 7.83–7.86 (m, 2H, 2 , 6 -H), 7.90–7.92 (m, 2H, 2 ,
6 -H); Anal. calcd for C H FN S (%): C, 63.66; H,
1
000
(
C=C str.); H NMR (400 MHz; CDCl , d ): 2.58 (s, 3H,
3
H
20 16
5
00
3
-CH ), 3.15 (s, 3H, 5-CH ), 7.27 (s, 1H, 5 -H), 7.40–7.44
3
4.24; N, 18.57. Found (%): C, 63.61; H, 4.22; N,
18.52.
3
0
0
0
(
m, 1H, 4 -H), 7.48–7.51 (m, 2H, 3 , 5 -H), 7.55–7.58 (m,
000 000 0 0
H, 3 , 5 -H), 7.76–7.79 (m, 2H, 2 , 6 -H), 7.83–7.85 (m,
2
2
3
00
000
00
0
(
E)-4 -(4 -Bromophenyl)-2 -(4-((4 -fluorophenyl)diazenyl)-
0
00
000
, 6 -H); Anal. calcd for C H BrN S (%): C, 54.67; H,
2
0
16
5
3
,5-dimethyl-1H-pyrazol-1-yl)thiazole 3n Yield: 86 %;
-
.64; N, 15.95. Found (%): C, 54.65; H, 3.61; N, 15.92.
1
m.p. 201–202 °C; IR (mmax, cm ): 1698 (C=N str.), 1562
(C=C str.); H NMR (400 MHz; CDCl , d ): 2.56 (s, 3H,
3-CH ), 3.13 (s, 3H, 5-CH ), 7.14–7.19 (m, 2H, 3 , 5 -H),
3
0
0
000
00
1
(
E)-4 -(4 -Chlorophenyl)-2 -(3,5-dimethyl-4-(phenyl-
3
H
0
0
diazenyl)-1H-pyrazol-1-yl)thiazole 3i Yield: 85 %;
-
3
1
00 000 000
m.p. 188–189 °C; IR (mmax, cm ): 1698 (C=N str.), 1566
7.26 (s, 1H, 5 -H), 7.54–7.58 (m, 2H, 3 , 5 -H),
7.75–7.78 (m, 2H, 2 , 6 -H), 7.83–7.86 (m, 2H, 2 , 6 -H);
Anal. calcd for C H BrFN S (%): C, 52.52; H, 3.28; N,
1
000
000
0
0
(
C=C str.); H NMR (400 MHz; CDCl , d ): 2.56 (s, 3H,
3
H
00
3
-CH ), 3.12 (s, 3H, 5-CH ), 7.21 (s, 1H, 5 -H), 7.37–7.42
3
3
20 15
5
0
000
000
0
0
(
m, 3H, 4 , 3 , 5 -H), 7.46–7.50 (m, 2H, 3 , 5 -H),
15.32. Found (%): C, 52.48; H, 3.26; N, 15.29.
1
23