V.A. Obakachi, N.D. Kushwaha, B. Kushwaha et al.
Journal of Molecular Structure 1241 (2021) 130665
CH3); 13C NMR (100 MHz, CDCl3) d 169.0 (C-2 of thiazole), 151.3 (d,
J=24.27 Hz, 1C), 148.1, 147.6(C-5 of thiazole), 138.4, 137.5, 132.2,
129.27 (d, J=23.33 Hz, 1 C), 126.86 (d, J=12.07 Hz, 1 C), 125.8,
(t, J=8.32 Hz, 1H, ArH), 7.36 (t, J=7.28, 1H, ArH), 7.16 (s, 1H,
ArH), 7.04 (s, 1H, ArH), 6.93 (d, J=17.79 Hz, 1H, ArH), 6.81 (d,
J=16.59 Hz, 1H, Ar-HC=CH-), 6.70 (d, J=16.43 Hz, 1H, Ar-HC=CH-),
4.02 (q, J=6.99 Hz, 2H, CH2), 3.78 (s, 6H, OCH3), 2.33 (s, 3H, CH3),
2.24 (s, 3H, CH3), 1.24 (t, J=6.98 Hz, 3H, CH3); 13C NMR (100 MHz,
DMSO-d6 25 °C) δ 158.6 (C-2 of thiazole), 151.5, 147.6, 138.2 (C-5
of thiazole), 132.1, 131.9, 129.7, 127.4, 127.4, 125.6, 122.4, 122.2,
122.2, 121.1, 105.4, 102.9, 70.85 (CH2), 21.31 (CH3), 15.33 (CH3),
+
14.37 (CH3), 11.01 (CH3). MS m/z 458.00 (M+H)
4.1.6.14.
.
4-(3,4-dimethoxyphenyl)-2-(2-((2E,3E)-4-(5-
ethoxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-3-en-2-
105.1, 104.8, 71.3(CH2), 56.5(OCH3), 15.4 (CH3), 14.4 (CH3), 13.3
+
ylidene)hydrazinyl)thiazole (7o); Brownish Solid, Yield: 68%,
mp: 190–193 °C; FTIR (ATR, vmax, cm-1): 3060.57 (Ar-H Str.),
2902.04 (C-H Str. of CH3), 1613.29 (C = N Str.); 1H NMR (400 MHz,
DMSO-d6 25 °C) δ 10.26 (s, 1H, NH), 7.67 (d, J=7.80 Hz, 2H, ArH),
7.51 (t, J=7.80 Hz, 2H, ArH), 7.38 (m, 3H, ArH), 7.19 (s, 1H, ArH),
6.99 (d, J=8.37 Hz, 1H, ArH), 6.77 (d, J=16.66 Hz, 1H, Ar-HC=CH-),
6.67 (d, J=16.66 Hz, 1H, Ar-HC=CH-), 4.01 (q, J=6.99 Hz, 2H, CH2),
3.79 (d, J=11.77 Hz, 6H, OCH3), 2.32 (s, 3H, CH3), 2.17 (s, 3H, CH3),
1.25 (t, J=7.02 Hz, 3H, CH3); 13C NMR (100 MHz, DMSO-d6 25 °C)
δ 159.5 (C-2 of thiazole), 151.2 (d, J = 8.80 Hz, 1C), 150.8, 148.8(d,
J = 4.37 Hz, 1C), 148.0, 138.2 (C-5 of thiazole), 138.1, 134.3, 129.0,
126.7, 126.3, 121.7, 121.6, 118.0, 112.4, 111.7, 109.2, 109.0, 94.6, 68.7
(CH3). MS m/z 504.00 (M+H)
4.1.6.10.
.
2-(2-((2E,3E)-4-(5-ethoxy-3-methyl-1-phenyl-
1H-pyrazol-4-yl)but-3-en-2-ylidene)hydrazinyl)-4-(4-
nitrophenyl)thiazole (7k); Brownish Solid, Yield: 75%, mp:166–
169 °C;FTIR (ATR, vmax, cm-1): 3069.55 (Ar-H Str.), 2981.67 (C-H
Str. of CH3), 1596.47 (C = N Str); 1H NMR (400 MHz, DMSO-d6
25 °C) δ 11.29 (brs, 1H, NH), 8.27 (d, J = 8.51 Hz, 2H, ArH), 8.11
(d, J = 8.69 Hz, 2H), 7.69–7.66 (m, 3H, ArH), 7.50 (t, J = 7.59 Hz,
2H, ArH), 7.34 (t, 7.32 Hz, 1H, ArH), 6.73 (d, J = 16.60 Hz, 1H,
Ar-HC=CH-), 6.64 (d, J = 16.60 Hz, 1H, Ar-HC=CH-), 3.99 (q,
J = 7.01 Hz, 2H, CH2), 2.31 (s, 3H, CH3), 2.15 (s, 3H, CH3), 1.24
(t, J = 6.94 Hz, 3H, CH3); 13C NMR (100 MHz, DMSO-d6 25 °C) δ
170.1 (C-2 of thiazole), 156.4, 151.0, 149.6(C-5 of thiazole), 147.4,
146.6, 141.2 (d, J = 11.1 Hz, 1C), 138.4, 129.6 (d, J = 4.4 Hz, 1C),
127.2 (d, J = 12.2 Hz 1C), 126.7 (d, J =4.5 Hz, 1C), 124.5 (d,
(CH2), 55.3 (d, J = 24.2 Hz, 1C, OCH3), 14.6 (CH3), 13.3 (CH3), 13.1
+
(CH3). MS m/z 504.00 (M+H)
.
4.1.6.15.
2-(2-((2E,3E)-4-(1-(3-chlorophenyl)-5-ethoxy-
3-methyl-1H-pyrazol-4-yl)but-3-en-2-ylidene)hydrazinyl)-4-
J = 16.0 Hz, 1C), 122.1, 121.8, 121.5, 105.2, 71.0 (CH2), 15.4 (CH3),
phenylthiazole (8a); Brownish Solid, Yield: 69%, mp: 195–198 °C;
FTIR (ATR, vmax, cm-1): 3087.50 (Ar-H Str.), 2981.46 (C-H Str. of
CH3), 1618.49 (C = N Str.); 1H NMR (400 MHz, CDCl3) d 11.31 (brs,
1H, NH), 7.74 (s, 1H, ArH), 7.70 (d, J=7.09 Hz, 2H, ArH), 7.60 (d,
J=8.16 Hz, 1H, ArH), 7.43 (t, J=7.26 Hz, 2H, ArH), 7.37 (m, 2H, ArH),
7.32 (d, J=8.17 Hz, 1H, ArH) 7.24 (s, 1H, ArH), 6.79 (d, J=16.75 Hz,
1H, Ar-HC=CH-), 6.71 (d, J=16.42 Hz, 1H, Ar-HC=CH-),), 4.00 (q,
J=7.04 Hz, 2H, CH2), 2.38 (s, 3H, CH3), 2.28 (s, 3H, CH3), 1.30 (t,
J=7.06 Hz, 3H, CH3); 13C NMR (100 MHz, DMSO-d6 25 °C) δ 169.1
(C-2 of thiazole), 150.7, 147.6 (C-5 of thiazole), 139.9, 134.5, 133.5,
131.1, 129.2, 128.5, 127.5, 126.3, 125.5, 124.6, 120.9, 120.5, 119.8,
+
14.3 (CH3), 12.4 (CH3). MS m/z 489.00 (M+H)
.
4.1.6.11.
2-(2-((2E,3E)-4-(5-ethoxy-3-methyl-1-phenyl-
1H-pyrazol-4-yl)but-3-en-2-ylidene)hydrazinyl)-4-(4-
methoxyphenyl)thiazole (7l); Light Brownish Solid, Yield:77%
mp:194–197 °C; FTIR (ATR, vmax, cm-1): 3117.31 (N-H Str.),
3041.74 (Ar-H Str.), 2978.63 (C-H Str. of CH3), 1612.09 (C = N Str.);
1H NMR (400 MHz, CDCl3 25 °C) δ 11.29 (brs, 1H, NH), 7.70–7.66
(m, 4H, ArH), 7.46–7.42 (m, 2H, ArH), 7.33–7.29 (m, 1H, ArH), 7.00–
6.69 (m, 2H, ArH), 6.86 (d, J = 16.84 Hz, 1H, Ar-HC=CH-), 6.74 (d,
J = 16.84 Hz, 1H, Ar-HC=CH-), 6.58 (s, 2H), 3.98 (q, J = 7.12 Hz,
2H, CH2), 3.84 (s, 3H, OCH3), 2.42 (s, 3H, CH3), 2.33 (s, 3H, CH3),
1.29 (t, J = 7.05 Hz, 3H, CH3); 13C NMR (100 MHz, CDCl3 25 °C) δ
169.0 (C-2 of thiazole), 160.9, 155.9, 151.8, 147.9 (C-5 of thiazole),
142.6, 138.2, 129.2, 127.3, 127.1, 125.4, 124.8, 122.5, 122.3, 121.4,
114.9, 105.2, 71.1 (CH2), 55.5 +(OCH3), 15.3 (CH3), 14.5 (CH3), 13.3
119.6, 105.2, 103.9, 70.8 (CH2), 14.9 (CH3), 13.8 (CH3), 11.9 (CH3).
+
MS m/z 480.00 (M+H)
.
4.1.6.16.
4-(4-bromophenyl)-2-(2-((2E,3E)-4-(1-(3-
chlorophenyl)-5-ethoxy-3-methyl-1H-pyrazol-4-yl)but-3-en-2-
ylidene)hydrazinyl)thiazole (8b); Brownish Solid, Yield: 71%,
mp: 198–201 °C; FTIR (ATR, vmax, cm-1): 3116.74 (N-H Str.),
2984.47 (Ar-H Str.), 2924.74 (C-H Str. of CH3), 1616.80 (C = N
Str.); 1H NMR (400 MHz, DMSO) d 11.40 (brs, 1H, NH), 7.81 (d,
J=8.36 Hz, 2H, ArH), 7.73 (s, 1H, ArH), 7.68 (d, J=7.22 Hz, 1H,
ArH), 7.59 (d, J=8.38 Hz, 2H, ArH), 7.53 (d, J=8.14 Hz, 1H, ArH),
7.40 (d, J=7.95 Hz, 1H, ArH), 7.35 (d, J=4.91 Hz, 1H, ArH), 6.72 (d,
J=16.93 Hz, 1H, Ar-HC=CH-), 6.64 (d, J=16.78 Hz, 1H, Ar-HC=CH-),
4.05 (q, J=7.02 Hz, 2H, CH2), 2.31 (s, 3H, CH3), 2.14 (s, 3H, CH3),
1.27 (t, J=6.95 Hz, 3H, CH3); 13C NMR (100 MHz, DMSO-d6 25 °C)
δ 169.1 (C-2 of thiazole), 150.6, 148.8, 147.6 (C-5 of thiazole), 139.0,
133.8, 133.4, 131.5, 131.0, 129.1, 127.5, 126.3, 124.5, 123.4, 120.9,
120.5, 120.4, 119.6, 115.1, 105.2, 104.8, 70+.8 (CH2), 14.9 (CH3), 13.8
(CH3). MS m/z 474.00 (M+H)
.
4.1.6.12.
4-(4-chlorophenyl)-2-(2-((2E,3E)-4-(5-
ethoxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-3-en-2-
ylidene)hydrazinyl)thiazole (7 m); Light Brownish Solid, Yield:
79%, mp: 135–137 °C; FTIR (ATR, vmax, cm-1): 3234.58 (N-H Str.),
3112.25 (Ar-H Str.), 2977.59 (C-H Str. of CH3), 1597.50 (C = N Str);
1H NMR (400 MHz, DMSO-d6 25 °C) δ 10.12 (brs, 1H, NH), 7.85
(d, J = 8.28 Hz, 2H, ArH), 7.65 (d, J = 7.36 Hz, 2H, ArH), 7.50
(t, J = 7.89 Hz, 2H, ArH), 7.44 (d, J = 8.65 Hz, 2H, ArH), 7.34 (t,
J = 7.13 Hz, 1H, ArH), 7.28 (s, 1H, ArH), 6.69 (d, J = 16.67 Hz,
1H, Ar-HC=CH-), 6.64 (d, J = 16.67 Hz, 1H, Ar-HC=CH-), 3.98 (q,
J = 7.04 Hz, 2H, CH2), 2.30 (s, 3H, CH3), 2.12 (s, 3H, CH3), 1.23
(t, J = 7.13 Hz, 3H, CH3); 13C NMR (100 MHz, DMSO-d6 25 °C) δ
169.9 (C-2 of thiazole), 150.7, 149.4, 148.9, 147.2(C-5 of thiazole),
138.0, 133.8, 132.0, 129.4, 128.8, 127.4, 127.0, 121.9, 120.7, 105.0,
(CH3), 11.9 (CH3). MS m/z 556.00 (M+H)
.
4.1.6.17. 2-(2-((2E,3E)-4-(1-(3-chlorophenyl)-5-ethoxy-3-
methyl-1H-pyrazol-4-yl)but-3-en-2-ylidene)hydrazinyl)-4-(4-
fluorophenyl)thiazole (8c); Brownish solid, Yield: 81%, mp:
195–198 °C; FTIR (ATR, vmax, cm-1): 3221.52 (N-H Str.), 3094.49
(Ar-H Str.), 2982.67 (C-H Str. of CH3), 1618.01 (C = N Str.); 1H
NMR (400 MHz, DMSO-d6 25 °C) δ 7.90 (m, J=3.55 Hz, 2H,
ArH), 7.73 (t, J=1.93 Hz, 1H, ArH), 7.68 (m, J=1.82 Hz, 1H, ArH),
7.59 (q, J=3.44 Hz, 1H, ArH), 7.41 (q, J=3.03 Hz, 1H, ArH), 7.26
(t, J=4.01 Hz, 2H, ArH), 7.22 (d, J=8.87 Hz, 2H, ArH), 6.73 (d,
J=16.60 Hz, 1H, Ar-HC=CH-), 6.65 (d, J=16.70 Hz, 1H, Ar-HC=CH-
),), 4.05 (q, J=7.02 Hz, 2H, CH2), 2.32 (s, 3H, CH3), 2.14 (s, 3H,
CH3), 1.28 (t, J=7.01 Hz, 3H, CH3); 13C NMR (100 MHz, DMSO-d6
25 °C) δ 169.2 (C-2 of thiazole), 162.8, 160.3, 150.7, 147.6 (C-5
104.6, 70.7 (CH2), 30.8 (CH3), 15.1 (CH3), 13.9 (CH3), 12.1 (CH3).
+
MS m/z 477.00 (M+H)
.
4.1.6.13. 2-(2-((2E,3E)-4-(5-ethoxy-3-methyl-1-phenyl-1H-pyrazol-
4-yl)but-3-en-2-ylidene)hydrazinyl)-4-(p-tolyl)thiazole (7n); Brown-
ish Solid, Yield:63% mp:125–128 °C; FTIR (ATR, vmax, cm-1):
3306.52 (N-H Str.), 3115.66 (Ar-H Str.), 2977.50 (C-H Str. of CH3),
1592.79 (C = N Str.) 1H NMR (400 MHz, CDCl3, 25 °C), δ 8.71
(s, 1H, NH), 7.69 (q, J=5.63 Hz, 4H, ArH), 7.44 (m, J=3.96 Hz, 2H,
ArH), 7.30 (m, J=3.99 Hz, 1H, ArH), 7.19 (d, J=7.92 Hz, 2H, ArH),
6.82 (s, 1H, ArH), 6.79 (d, J=16.72 Hz, 1H, Ar-HC=CH-), 6.64 (d,
J=16.72 Hz, 1H, Ar-HC=CH-), 3.99 (q, J=7.06 Hz, 2H, CH2), 2.41 (s,
3H, CH3), 2.36 (s, 3H, CH3), 2.05 (s, 3H, CH3), 1.30 (t, J=7.07 Hz, 3H,
13