L. Kumar, K. Lal, A. Kumar et al.
Journal of Molecular Structure 1246 (2021) 131154
4.3.14.
culated for C28H25BrN6O3 [M+H]+: 573.1244, [M+2]+: 575.1224
2-(4-((4-(1-acetyl-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-5-
yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-(4-nitrophenyl)acetamide
(6n)
found: 573.1246, 575.1234
4.3.17. 2-(4-((4-(1-acetyl-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-
5-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-(p-tolyl)acetamide
(6q)
Brown solid; Yield 86%; m.p.: 117-120°C; FT-IR (KBr, υmax
cm−1): 3278 (N-H amide str.), 3152 (C-H str., triazole ring), 3091
(C-H str., aromatic ring), 2927 (C-H str., aliphatic), 1641 (C=O str.,
Brown solid; Yield 86%; m.p.: 141-142°C; FT-IR (KBr, υmax
cm−1): 3267 (N-H amide str.), 3134 (C-H str., triazole ring), 3068
(C-H str., aromatic ring), 2938 (C-H str., aliphatic), 1664 (C=O str.,
amide), 1509, 1435 (C=C str., aromatic ring) cm−1
;
1H NMR (400
MHz, CDCl3): 11.10 (s, 1H, NH), 8.26 (d, J = 7.0 Hz, 3H, Ar-H), 7.83
(d, J = 7.6 Hz, 2H, Ar-H), 7.73 (d, J = 6.9 Hz, 2H, 1Ar-H & C-H tri-
azole), 7.12 (d, J = 6.1 Hz, 2H), 7.01 (s, 4H), 5.49 (dd, 1H, J = 11.6,
4.5 Hz), 5.44 (s, 2H), 5.16 (s, 2H), 3.81 (dd, J = 16.6, 11.6 Hz, 1H),
3.79 (s, 3H), 3.10 (dd, J = 16.6, 4.5 Hz, 1H), 2.51 (s, 3H, COCH3);
13C NMR (100 MHz, CDCl3): 167.53 (C=O), 165.81 (C=O), 161.38
(Ar-C), 157.65 (Ar-C), 154.46 (Pyrazoline-C), 144.97 (C4 triazole),
143.08 (Ar-C), 135.40 (Ar-C), 128.76 (Ar-C), 127.25 (Ar-C), 126.73
(Ar-C), 125.60 (Ar-C), 124.13 (C5 triazole), 119.52 (Ar-C), 115.18
(Ar-C), 114.68 (Ar-C), 61.48 (Pyrazoline-C), 59.17 (OCH2), 55.81,
52.79 (NCH2), 42.62 (Pyrazoline-C), 22.22 (COCH3); HRMS: (m/z)
[M+H]+calculated for C29H27N7O6: 570.2096 found: 570.2099
amide), 1511, 1420 (C=C str., aromatic ring) cm−1
;
1H NMR (400
MHz, CDCl3): δ 8.40 (s, 1H, NH), 7.78 (s, 1H, C-H triazole), 7.60
(q, J = 8.6 Hz, 4H, Ar-H), 7.38 (d, J = 8.3 Hz, 2H, Ar-H), 7.14
(t, J = 9.2 Hz, 4H, Ar-H), 6.92 (d, J = 8.5 Hz, 2H), 5.56 (dd,
J = 11.8, 4.7 Hz, 1H, Pyrazoline-H), 5.16 (s, 2H, -OCH2), 4.93 (s,
2H, NCH2), 3.73 (dd, J = 17.7, 11.9 Hz, 1H, Pyrazoline-H), 3.13
(dd, J = 17.7, 4.7 Hz, 1H, Pyrazoline-H), 2.45 (s, 3H, COCH3), 2.33
(s, 3H); 13C NMR (100 MHz, CDCl3): 169.11 (C=O), 162.79 (Ar-
C), 157.70 (Pyrazoline-C), 153.15 (Ar-C), 148.02 (Ar-C), 142.99 (C4
triazole), 134.70 (Ar-C), 134.60 (Ar-C), 132.01 (Ar-C), 130.27 (Ar-
C), 129.56 (Ar-C), 128.05 (Ar-C), 126.92 (Ar-C), 124.78 (C5 tria-
zole), 124.60 (Ar-C), 120.15 (Ar-C), 115.19(Ar-C), 61.98 (Pyrazoline-
C), 59.77 (OCH2), 53.23 (NCH2), 42.28 (Pyrazoline-C), 22.03
(COCH3), 20.87(CH3).; HRMS (m/z) calculated for C29H27BrN6O3
[M+H]+:587.1401, [M+2]+: 589.1380 found: 587.1303, 589.1283
4.3.15. 2-(4-((4-(1-acetyl-3-(4-methoxyphenyl)-4,5-dihydro-1H-
pyrazol-5yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-(naphthalen-1-
yl)acetamide
(6o)
4.3.18. 2-(4-((4-(1-acetyl-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-
5-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-(4-
fluorophenyl)acetamide
Brown solid; Yield 92%; m.p.: 130-132°C; FT-IR (KBr, υmax
cm−1): 3272 (N-H amide str.), 3146 (C-H str., triazole ring), 3050
(C-H str., aromatic ring), 2936 (C-H str., aliphatic), 1628 (C=O str.,
(6r)
amide), 1509, 1458 (C=C str., aromatic ring) cm−1
;
1H NMR (400
Brown solid; Yield 90%; m.p.: 120-122°C; FT-IR (KBr, υmax
cm−1): 3284 (N-H amide str.), 3154 (C-H str., triazole ring), 3067
(C-H str., aromatic ring), 2935 (C-H str., aliphatic), 1639 (C=O str.,
MHz, CDCl3): δ 9.34 (s, 1H, NH), 7.87 (d, J = 7.0 Hz, 2H, Ar-H),
7.85 (s, 1H), 7.79 (s, 1H, C-H triazole), 7.68 (d, J = 8.6 Hz, 3H), 7.48
(m, 2H), 7.42 (t, J = 7.9 Hz, 1H), 7.14 (d, J = 8.4 Hz, 2H), 6.95 (d,
J = 8.7 Hz, 2H), 6.87 (d, J = 8.5 Hz, 2H), 5.50 (dd, J = 11.6, 4.3 Hz,
1H, Pyrazoline-H), 5.11 (s, 2H, -OCH2), 5.01 (s, 2H, -NCH2), 3.87 (s,
3H), 3.68 (dd, J = 17.6, 11.7 Hz, 1H, Pyrazoline-H), 3.09 (dd, J = 17.6,
4.4 Hz, 1H, Pyrazoline-H), 2.40 (s, 3H). 13C NMR (100 MHz, CDCl3):
δ 169.00 (C=O), 164.16 (C=O), 161.48 (Ar-C), 157.60 (Ar-C), 154.28
(Ar-C), 144.43 (C4 triazole), 134.80 (Ar-C), 134.04 (Ar-C), 131.75
(Ar-C), 128.53 (Ar-C), 128.27 (Ar-C), 127.10 (Ar-C), 126.84 (Ar-C),
126.40 (Ar-C), 126.16 (Ar-C), 126.08 (Ar-C), 125.53 (C5 triazole),
124.88 (Ar-C), 123.85 (Ar-C), 121.17 (Ar-C), 120.85 (Ar-C), 115.08
(Ar-C), 114.19 (Ar-C), 61.90 (Pyrazoline-C), 59.51 (OCH2), 55.41,
52.99 (NCH2), 42.57(Pyrazoline-C), 22.02 (COCH3); HRMS: (m/z)
[M+H]+calculated for C33H30N6O4: 575.2401 found: 575.2413
amide), 1509, 1431 (C=C str., aromatic ring) cm−1
;
1H NMR (400
MHz, CDCl3): δ 9.86 (s, 1H, NH), 7.56 (d, J = 7.8 Hz, 2H, 1Ar-H &
C-H triazole), 7.50 (d, J = 7.7 Hz, 4H, Ar-H), 7.28 (s, 1H, Ar-H), 7.10
(s, 2H), 6.93 (s, 4H), 5.50 (dd, J = 7.3, 4.1 Hz, 1H, Pyrazoline-H),
5.17 (s, 2H, -OCH2), 5.12 (s, 2H, -NCH2), 3.67 (dd, J = 17.2, 11.7 Hz,
1H, Pyrazoline-H), 3.07 (dd, J = 17.6, 3.7 Hz, 1H, Pyrazoline-H), 2.35
(s, 3H, COCH3); 13C NMR (100 MHz, CDCl3): 169.18 (C=O), 163.48
(C=O), 161.58 (Ar-C), 157.69 (Ar-C), 154.69 (Pyrazoline-C), 143.82
(C4 triazole), 137.81 (Ar-C), 134.72 (Ar-C), 128.99 (Ar-C), 128.38
(Ar-C), 126.81 (Ar-C), 124.80 (C5 triazole), 124.48 (Ar-C), 123.71
(Ar-C), 119.84 (Ar-C), 115.03 (Ar-C), 114.23 (Ar-C), 61.91(Pyrazoline-
C), 59.67 (OCH2), 55.45, 52.40 (NCH2), 42.74 (Pyrazoline-C), 22.17
(COCH3); HRMS: (m/z) calculated for C28H24BrFN6O3 [M+H]+:
591.1150, [M+2]+: 593.1130 found: 591.1159, 593. 1138
4.3.16. 2-(4-((4-(1-acetyl-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-
5-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenylacetamide
(6p)
4.3.19.
2-(4-((4-(1-acetyl-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-5-
yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-(4-nitrophenyl)acetamide
(6s)
Brown solid; Yield 86%; m.p.: 127-129°C; FT-IR (KBr, υmax
cm−1): 3244 (N-H amide str.), 3152 (C-H str., triazole ring), 3091
(C-H str., aromatic ring), 2926 (C-H str., aliphatic), 1641 (C=O str.,
Brown solid; Yield 83%; m.p.: 225-228°C; FT-IR (KBr, υmax
cm−1): 3248 (N-H amide str.), 3152 (C-H str., triazole ring), 3082
(C-H str., aromatic ring), 2931 (C-H str., aliphatic), 1632 (C=O
amide), 1509, 1435 (C=C str., aromatic ring) cm−1
;
1H NMR (400
MHz, CDCl3): 9.07 (s, 1H, NH), 7.74 (s, 1H, C-H triazole), 7.71 (d,
J = 8.6 Hz, 2H, Ar-H), 7.43 (d, J = 8.0 Hz, 2H, Ar-H), 7.13 (t,
J = 9.3 Hz, 4H), 6.96 (d, J = 8.5 Hz, 2H), 6.87 (d, J = 8.2 Hz,
2H), 5.53 (dd, J = 11.4, 4.2 Hz, 1H, Pyrazoline-H), 5.08 (s, 2H,
OCH2), 4.69 (s, 2H, NCH2), 3.88 (s, 3H), 3.73 (dd, J = 17.7, 11.8 Hz,
1H, Pyrazoline-H), 3.13 (dd, J = 17.6, 4.2 Hz, 1H, Pyrazoline-H),
2.47 (s, 3H), 2.32 (s, 3H, COCH3); 13C NMR (100 MHz, CDCl3):
169.18 (C=O), 163.48 (C=O) (Ar-C), 161.58 (C=O), 157.69 (Ar-C),
154.69 (Pyrazoline-C), 143.82 (C4 triazole), 137.81 (Ar-C), 134.72
(Ar-C), 128.99 (Ar-C), 128.38 (Ar-C), 126.81 (Ar-C), 124.80 (C5 tri-
azole), 124.48 (Ar-C), 123.71 (Ar-C), 119.84 (Ar-C), 115.03 (Ar-C),
114.23 (Ar-C), 61.91 (Pyrazoline-C), 59.67 (OCH2), 55.45, 52.40
(NCH2), 42.74 (Pyrazoline-C), 22.17 (COCH3); HRMS: (m/z) cal-
str., amide), 1508, 1451 (C=C str., aromatic ring) cm−1
;
1H NMR
(400 MHz, CDCl3): 10.26 (s, 1H, NH), 8.19 (d, J = 9.0 Hz, 2H,
Ar-H), 7.86 (s, 1H), 7.77 (d, J = 8.0 Hz, 2H, 1Ar-H & C-H tri-
azole), 7.58 (d,
J
=
11.8 Hz, 4H, Ar-H), 7.15 (d,
J
=
8.7 Hz,
2H), 6.93 (d, J = 8.2 Hz, 2H), 5.55 (dd, J = 11.3, 4.1 Hz, 1H,
Pyrazoline-H), 5.19 (d, 2H, -OCH2), 5.14 (d, 2H, -NCH2), 3.72
(dd,
J
=
17.6, 11.9 Hz, 1H, Pyrazoline-H), 3.12 (dd,
J
=
19.3,
4.4 Hz, 1H, Pyrazoline-H), 2.41 (s, 3H, COCH3); 13C NMR (100
MHz, CDCl3): 169.18 (C=O), 163.48 (C=O), 161.58 (Ar-C), 157.69
(Ar-C), 154.69 (Pyrazoline-C), 143.82 (C4 triazole), 137.81(Ar-C),
134.72 (Ar-C), 128.99 (Ar-C), 128.38 (Ar-C), 126.81 (Ar-C), 124.80
(C5 triazole), 124.48 (Ar-C), 123.71(Ar-C), 119.84 (Ar-C), 115.03
9