S. Punia, V. Verma and D. Kumar et al. / Journal of Molecular Structure 1223 (2020) 129216
9
colour, yield: 58%, M.P.:148-150°C, 1H NMR (400 MHz, DMSO)
δ 10.34 (s, 1H, amide N-H), 8.30 (d, J = 2.4 Hz, 1H, pyrazole
C3-H), 8.02 (s, 1H, triazole ring H), 7.96 (bs, 1H), 7.91 (bd, J = 1.2
Hz, 1H, pyrazole C5-H), 7.80 (s, 1H, imidazole ring H), 7.46 (dd,
J = 4.0 Hz, 3H), 7.38 (t, J = 7.6, 7.2 Hz, 2H, imidazole C4-phenyl
C3/C5-H), 7.25 (t, J = 7.6, 7.2 Hz, 1H, imidazole C4-phenyl C4-H),
7.13 (dd, J = 4.0 Hz, 2H), 6.60 (t, J = 2.0, 2.4 Hz, 1H, pyrazole
C4-H), 5.52 (s, 2H, COCH2), 5.27 (s, 2H, CH2), 2.26 (s, 3H, CH3). IR
(KBr, ʋmax) = 3295 (N-H Str.), 3136 (C–H str., triazole), 3037 (C–H
str., aromatic), 1699 (C = O str.), 1610 (N-H bending) cm−1. HRMS:
m/z (M + H)+ Cacld. for C24H21N8O: 467.1989 found 467.2298.
Due to poor solubility 13C NMR of compound is not available.
aromatic), 1670 (C=O str.), 1640 (N-H bending) cm−1. HRMS: m/z
(M + H)+ Cacld. for C23H18 Cl2N8O: 493.1053 found 493.1080.
4.1.5.6. N-(3,4-Dichlorophenyl)-2-(4-((5-phenyl-2-(1H-pyrazol-1-
yl)-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)acetamide
(6f).
White colour, yield: 66%, M.P.:145-147°C, 1H NMR (400 MHz,
DMSO) δ 10.74 (s, 1H, amide N-H), 8.30 (d, J = 2.0 Hz, 1H, pyra-
zole C3-H), 8.03 (s, 1H, triazole ring H), 7.93 (d, J = 2.0 Hz, 1H,
pyrazole C5-H), 7.91 (s, 1H, 2,3-dichlorophenyl C2-H), 7.80 (s, 1H,
imidazole ring H), 7.78 (d, J = 7.6 Hz, 2H, imidazole C4-phenyl
C2/C6-H), 7.60 (d, J = 8.8 Hz, 1H, 2,3-dichlorophenyl ring H), 7.47
(dd, J = 8.8 Hz, 1H, 2,3-dichlorophenyl ring H), 7.38 (t, J = 7.6
Hz, 2H, imidazole C4-phenyl C3/C5-H), 7.24 (t, J = 7.2 Hz, 1H,
imidazole C4-phenyl C4-H), 6.60 (t, J = 1.6, 2.0 Hz, 1H, pyrazole
C4-H), 5.52 (s, 2H, COCH2), 5.33 (s, 2H, CH2).13C NMR (100 MHz,
DMSO) δ 165.08 ( COCH2), 140.11, 138.54, 138.09, 133.52, 132.16,
131.64, 131.29, 129.16, 127.48, 126.04, 125.80, 124.67, 121.11, 119.92,
117.17, 108.01 (aromatic ring C), 52.53 (COCH2), 41.82 ( CH2). IR
(KBr, ʋmax) = 3255 (N-H Str.), 3136 (C–H str., triazole), 3037 (C–H
str., aromatic), 1693 (C=O str.), 1618 (N-H bending) cm−1. HRMS:
m/z (M + H)+ Cacld. for C23H18 Cl2N8O: 493.1053 found 493.1352.
4.1.5.3. N-(3-Chloro-2-methylphenyl)-2-(4-((5-phenyl-2-(1H-pyrazol-
1-yl)-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)acetamide (6c).
Brown colour, yield: 74%, M.P.:155-156°C, 1H NMR (400 MHz,
DMSO) δ 10.02 (s, 1H, amide N-H), 8.29 (d, J = 2.4 Hz, 1H,
pyrazole C3-H), 8.02 (s, 1H, triazole ring H), 7.90 (d, J = 1.2
Hz, 1H, pyrazole C5-H), 7.80 (s, 1H, imidazole ring H), 7.77 (bd,
J = 7.2 Hz, 2H, imidazole C4-phenyl C2/C6-H), 7.40 – 7.30 (m, 4H,
imidazole C4-phenyl C3/C5-H and 1H of 2-methyl-3-chlorophenyl
ring), 7.26 – 7.20 (m, 2H, imidazole C4-phenyl C4-H and 2H of
2-methyl-3-chlorophenyl ring), 6.60 (t, J = 2.4, 2.0 Hz 1H, pyrazole
4.1.5.7. N-(3-Fluorophenyl)-2-(4-((5-phenyl-2-(1H-pyrazol-1-yl)-1H-
C4-H), 5.52 (s, 2H, COCH2), 5.36 (s, 2H, CH2), 2.24 (s, 3H, CH3).13
C
imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)acetamide
(6g). White
NMR (100 MHz, DMSO) δ 164.97 ( COCH2), 142.58, 140.11, 138.08,
137.12, 134.34, 133.66, 132.14, 130.93, 129.12, 127.47, 127.41, 127.06,
125.70, 124.82, 124.67, 117.18, 107.93 (aromatic ring C), 52.26
(COCH2), 41.90 ( CH2), 15.42. IR (KBr, ʋmax) = 3251 (N-H Str.), 3135
(C–H str., triazole), 3030 (C–H str., aromatic), 1695 (C=O str.), 1622
(N-H bending) cm−1. HRMS: m/z (M + H)+Cacld. for C24H21ClN8O:
473.9369 found 473.1600.
colour, yield: 60%, M.P.:168-170°C, 1H NMR (400 MHz, DMSO) δ
10.71 (s, 1H, amide N-H), 8.24 (d, J = 2.4 Hz, 1H, pyrazole C3-H),
7.99 (s, 1H, triazole ring H), 7.88 (d, J = 1.6 Hz, 1H, pyrazole
C5-H), 7.75 (bd, J = 9.2 Hz, 3H, imidazole C4-phenyl C2/C6-H and
imidazole ring H), 7.49 (bd, J = 11.6 Hz, 1H. imidazole ring H),
7.40 – 7.33 (m, 3H), 7.24 (t, J = 7.6 Hz, 1H, imidazole C4-phenyl
C5-H), 6.94-6.6.89 (m, 1H,), 6.58 (t, J = 2.0 Hz, 1H, pyrazole C4-H),
5.49 (s, 2H, COCH2), 5.28 (s, 2H, CH2).13C NMR (100 MHz, DMSO)
δ 164.91 ( COCH2), 142.61, 140.27, 140.16, 140.11, 138.07, 133.58,
132.15, 129.14, 127.45, 125.77, 124.67, 117.17, 115.58, 107.97, 106.77,
106.50 (aromatic ring C), 79.36, 52.57 (COCH2), 41.85 ( CH2). IR
(KBr, ʋmax) = 3282 (N-H Str.), 3130 (C–H str., triazole), 3045 (C–H
str., aromatic), 1695 (C = O str.), 1614 (N-H bending) cm−1. HRMS:
m/z (M + H)+ Cacld. for C23H19FN8O: 445.3539 found 445.3578.
4.1.5.4. N-(4-Chlorophenyl)-2-(4-((5-phenyl-2-(1H-pyrazol-1-yl)-1H-
imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)acetamide
(6d). Brown
colour, yield: 84%, M.P.:124-126°C, 1H NMR (400 MHz, DMSO) δ
10.59 (s, 1H, amide N-H), 8.29 (d, J = 2.4 Hz, 1H, pyrazole C3-H),
8.02 (s, 1H, triazole ring H), 7.90 (d, J = 1.4 Hz, 1H, pyrazole
C5-H), 7.80 (s, 1H, imidazole ring H), 7.77 (d, J = 7.3 Hz, 2H, imi-
dazole C4-phenyl C2/C6-H), 7.58 (d, J = 8.8 Hz, 2H, 4-chlorophenyl
C3/C5-H), 7.41 – 7.36 (m, 4H, imidazole C4-phenyl C3/C5-H and 4-
chlorophenyl C2/C6-H), 7.24 (t, J = 7.2 Hz, 1H, imidazole C4-phenyl
C4-H), 6.60 (t, J = 2.0, Hz 1H, pyrazole C4-H), 5.52 (s, 2H, COCH2),
5.31 (s, 2H, CH2).13C NMR (100 MHz, DMSO) δ 164.73 ( COCH2),
142.80, 142.51, 138.03, 137.75, 133.83, 132.15, 129.29, 129.06,
127.84, 127.29, 125.71, 124.65, 121.26, 117.21, 107.83 (aromatic ring
C), 52.64 (COCH2), 42.00 ( CH2). IR (KBr, ʋmax) = 3251 (N-H Str.),
3135 (C–H str., triazole), 3030 (C–H str., aromatic), 1695 (C=O
str.), 1622 (N-H bending) cm−1. HRMS: m/z (M + H)+Cacld. for
C23H19ClN8O: 459.1443 found 459.1486.
4.1.5.8. N-(2-Nitrophenyl)-2-(4-((5-phenyl-2-(1H-pyrazol-1-yl)-1H-
imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)acetamide (6h). Yellow
colour, yield: 63%, M.P.: 145-150°C, 1H NMR (400 MHz, DMSO) δ
10.71 (s, 1H, amide N-H), 8.28 (d, J = 2.4 Hz, 1H, pyrazole C3-H),
8.00-7.97 (m, 2H, imidazole ring H and triazole ring H), 7.90 (d,
J = 1.2 Hz, 1H, pyrazole C5-H), 7.78 – 7.67 (m, 5H, imidazole
C4-phenyl C2/C6-H), 7.44 – 7.36 (m, 3H), 7.24 (t, J = 7.6, 7.2 Hz,
1H, imidazole C4-phenyl C4-H), 6.59 (t, J = 2.0 Hz, 1H, pyrazole
C4-H), 5.51 (s, 2H, COCH2), 5.38 (s, 2H, CH2). IR (KBr, ʋmax) = 3292
(N-H Str.), 3140 (C–H str., triazole), 3035 (C–H str., aromatic), 1691
(C=O str.), 1614 (N-H bending) cm−1. HRMS: m/z (M + H)+ Cacld.
for C23H19N9O3: 470.1684 found 470.1594.
4.1.5.5. N-(2,3-Dichlorophenyl)-2-(4-((5-phenyl-2-(1H-pyrazol-1-
yl)-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)acetamide
(6e).
White colour, yield: 74%, M.P.:130-132°C, 1H NMR (400 MHz,
DMSO) δ 10.20 (s, 1H, amide N-H), 8.29 (d, J = 2.4 Hz, 1H, pyra-
zole C3-H), 8.02 (s, 1H, triazole ring H), 7.90 (d, J = 1.6 Hz, 1H,
pyrazole C5-H), 7.80 (s, 1H, imidazole ring H), 7.77 (d, J = 7.2 Hz,
2H, imidazole C4-phenyl C2/C6-H), 7.71 (dd, J = 8.4 Hz, 1H, 2,3-
dichlorophenyl ring H), 7.49 (dd, J = 8.0 Hz, 1H, 2,3-dichlorophenyl
ring H), 7.37 (dd, J = 16 Hz, 3H, imidazole C4-phenyl C3/C5-H and
2,3-dichlorophenyl ring H), 7.24 (t, J = 7.2 Hz, 1H, imidazole C4-
phenyl C4-H), 6.60 (t, J = 2.0, 2.4 Hz 1H, pyrazole C4-H), 5.52 (s,
2H, COCH2), 5.42 (s, 2H, CH2).13C NMR (100 MHz, DMSO) δ 165.32
( COCH2), 142.85, 142.60, 140.12, 138.10, 136.25, 133.61, 132.47,
132.14, 129.13, 128.63, 127.72, 127.44, 125.77, 124.95, 124.68, 117.17,
107.96 (aromatic ring C), 52.33 (COCH2), 41.86 ( CH2). IR (KBr,
4.1.5.9. N-(Naphthalen-1-yl)-2-(4-((5-phenyl-2-(1H-pyrazol-1-yl)-
1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)acetamide (6i). Grey
colour, yield: 85%, M.P.:180-182°C, 1H NMR (400 MHz, DMSO) δ
10.39 (s, 1H, amide N-H), 8.30 (d, J = 2.4 Hz, 1H, pyrazole C3-H),
8.13 (bd, J = 8.8 Hz, 1H, α-naphthyl ring H), 8.07 (s, 1H, triazole
ring H), 7.96 (bd, J = 7.6 Hz, 1H, α-naphthyl ring H), 7.91 (d,
J = 2.0 Hz, 1H, pyrazole C5-H), 7.81 (s, 2H), 7.78 (bd, J = 8.8
Hz, 2H, imidazole C4-phenyl C2/C6-H), 7.70 (d, J = 7.6 Hz, 1H,
α-naphthyl ring H), 7.60 – 7.56 (m, 2H, α-naphthyl ring H), 7.50
(t, J = 8.0 Hz, 1H, α-naphthyl ring H), 7.38 (t, J = 7.2, 8.0 Hz, 2H,
imidazole C4-phenyl C3/C5-H), 7.24 (t, J = 7.2, 7.6 Hz, 1H, imidazole
C4-phenyl C4-H), 6.59 (t, J = 2.0, 1H, pyrazole C4-H), 5.53 (s, 2H,
COCH2), 5.50 (s, 2H, CH2).13C NMR (100 MHz, DMSO) δ 167.60
( COCH2), 142.49, 138.06, 134.17, 133.25, 132.15, 129.04, 128.63,
ʋmax) = 3241 (N-H Str.), 3125 (C–H str., triazole), 3020 (C–H str.,