J. Chem. Sci.
(2019) 131:62
Page 3 of 7
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−CH3), 7.13 (d, J = 7.6 Hz, 2H, ArH), 7.26 (d, J = 8.3 Hz,
J = 8.3 Hz, 1H, ArH), 7.99 (t, J = 6.9 Hz, 2H, ArH), 12.60
2H, ArH), 7.45 (dd, J = 27.2, 7.9 Hz, 4H, ArH), 7.55 (m, (s,1H, NH); MS (m/z):Calcd.406.16, found 407.14 [M+1].
2H, ArH), 7.95 (dd, J = 13.4 Hz, 7.9 Hz, 2H, ArH), 8.00
(d, J = 8.3 Hz, 1H, ArH), 8.24 (dd, J = 8.6 Hz,1.7 Hz, 1H,
2.2i 4-(4-chlorophenyl)-2-(napthalen-1-yl)-5-phenyl-
ArH), 8.60 (s, 1H, ArH), 12.74 (s, 1H, NH); 13C NMR (400
1H-imidazole ( 2i): Off white solid; M.p. 255−257 ◦C;
MHz, DMSO−d6), δ (ppm): 15.9, 118.5, 118.6, 121.3, 121.7,
FT-IR (KBr, cm−1
)
max: 3418.21 (N-H), 3049.87 (Ar-H),
ν
122.7, 122.9, 123.1, 123.2, 124.0, 127.7, 128.0, 131.4, 141.2;
1
1599.66 (C=C), 1583.27 (C=N), 745.35 (C-Cl); H NMR
(500 MHz, DMSO − d6) δ (ppm): 7.39 (t, J = 7.2 Hz,
1H, ArH), 7.41 (d, J = 7.6 Hz, 2H, ArH) ,7.49 (m,2H, ArH),
7.57 (d, J = 6.9 Hz, 2H, ArH),7.63 (m,5H, ArH), 7.96 (d,
J = 7.6 Hz, 1H, ArH), 8.01 (d, J = 7.6 Hz, 2H, ArH), 9.14
(d, J= 8.3 Hz, 1H, ArH), 12.85 (s,1H,NH); 13C NMR (400
MHz, DMSO − d6) δ (ppm): 120.3, 121.2, 121.5, 121.8,
122.4, 123.0, 123.3, 123.4, 123.5, 123.5, 123.7, 123.8, 124.1,
125.0, 125.4, 125.8, 126.0, 127.2, 128.7, 129.2, 130.1, 130.9,
132.7, 140.8, 140.9; MS (m/z): Calcd.380.10, found 381.14
[M+1].
MS (m/z): Calcd. 374.17, found 375.05 [M+1].
2.2e 4,5-bis(4-bromophenyl)-2-(naphthalen-1-yl)-1H
-imidazole (2e): Yellow solid; M.p.: 205 − 207 ◦C; FT-IR
(KBr, cm−1
)
max: 3417.28 (N-H), 1600.63 (C=C), 1584.24
ν
(C=N), 832; 1H NMR (500 MHz, CDCl3) δ (ppm): 6.55 (m,
2H, ArH), 6.64 (d, J = 1.8 Hz, 2H, ArH), 7.56 (m, 4H, ArH),
7.64 (m, 2H, ArH), 7.6 (d, J = 3.4 Hz, 2H, ArH), 7.78 (d,
J = 7.6 Hz, 2H, ArH), 8.7 (d,J = 8.3 Hz, 1H, ArH), 9.61
(s, 1H, NH); 13C NMR (400 MHz, DMSO − d6) δ (ppm):
121.2, 121.8, 121.9, 124.3, 125.3, 126.4, 126.7, 126.8, 127.6;
MS (m/z): Calcd.501.96, found 500.98 [M-1].
2.2j 4-(4-chlorophenyl)-2-(napthalen-2-yl)-5-phenyl-
1H-imidazole (2j): Pale brown solid; M.p. 222−224 ◦C;
FT-IR (KBr, cm−1
)
max: 3442.31 (N-H), 3056.62 (Ar-H),
ν
2.2f 2-(naphthalen-1-yl)-4,5-diphenyl-1H-imidazole
(2f): Pale yellow solid; M.p.: 262−263 ◦C; FT-IR (KBr,
νmax
1580.38 (C=N), 753.06 (C-Cl);1H NMR (500 MHz, DMSO−
d6) δ (ppm): 7.40 (m, 4H, ArH), 7.53 (m, 7H, ArH), 7.96 (q,
J = 7.6 Hz,2H, ArH), 8.02 (d, J = 9.0 Hz, 1H, ArH), 8,25
(dd, J = 8.6 Hz,1.7 Hz, 1H, ArH), 8.61 (s,1H, ArH), 12.92
(s, 1H, NH); 13C NMR (400 MHz, DMSO − d6) δ (ppm):
118.5, 118.8, 121.4, 121.8, 122.7, 122.8, 123.2, 123.3, 123.6,
127.8, 128.0, 140.8; MS (m/z):Calcd.380.10, found 380.98
[M+1].
cm−1
)
: 3417.24 (N-H), 3052.69 (Ar-H), 1600.63
(C=C), 1584.24 (C=N); 1H NMR (500 MHz, DMSO−d6) δ
(ppm): 7.25 (t, J = 7.6 Hz, 1H, ArH), 7.36 (m, 3H, ArH),
7.45 (t, J = 7.6 Hz, 2H, ArH), 7.57 (m, 2H, AH), 7.62(m, 5H,
AH), 7.97 (d, J = 8.3 Hz, 1H, ArH), 8.01 (d, J = 8.3 Hz,
2H, ArH), 9.18 (d, J = 9.0 Hz, 1H, ArH), 12.79 (s, 1H, NH);
13C NMR (400 MHz, DMSO − d6), δ (ppm): 120.3, 121.1,
121.7, 121.8, 122.2, 122.5, 122.7, 123.0, 123.3, 123.4, 123.7,
124.0, 125.4, 126.1, 128.7, 130.4, 132.2, 140.6; MS (m/z):
Calcd.346.14, found 347.02 [M+1].
2.2k 4,5-di(furan-2-yl)-2-(naphthalen-2-yl)-1H-imid-
azole (2k): Brown solid; M.p. 248−251 ◦C; FT-IR (KBr,
νmax
cm−1
)
: 3417.24 (N-H), 3057.58 (Ar-H), 1601.59
(C=C), 1555.31 (C=N); 1H NMR (500 MHz, DMSO−d6) δ
(ppm): 6.61 (d,J = 42.7 Hz, 2H, ArH), 6.80 (dd,J =
100.0 Hz, J = 2.8 Hz, 2H,ArH), 7.57 (m,2H, ArH), 7.81
(d,J = 57.2 Hz, 2H, ArH), 7.96 (d,J = 7.6 Hz, 1H,ArH),
8.01 (t,J = 10.0 Hz, 2H, ArH), 8.25 (d, J = 9.0 Hz, 1H,
ArH), 8.67 (s, 1H, ArH), 13.05 (s, 1H, NH); 13C NMR (400
MHz, DMSO − d6), δ (ppm): 102.0, 103.5, 106.4, 107.0,
114.7, 118.6, 119.4, 121.6, 121.8, 122.2, 122.7, 123.2, 123.3,
124.8, 127.9, 136.9, 137.7, 139.5, 141.3, 144.3; MS (m/z):
Calcd.326.10, found 327.11 [M+1].
2.2g 2-(naphthalen-2-yl)-4,5-diphenyl-1H-imidazole
(2g): Pale yellow solid; M.p.: 257−260 ◦C; FT-IR (KBr,
νmax
cm−1
)
: 3417.24 (N-H), 3054.69 (Ar-H), 1600.63
(C=C), 1584.01 (C=N); 1H NMR (500 MHz, DMSO−d6) δ
(ppm): 7.25 (t, J = 7.6 Hz, 1H,ArH), 7.33 (t, J = 7.6 Hz,
2H,ArH), 7.40 (t, J = 7.2 Hz, 1H, ArH), 7.47 (t, J =
7.6 Hz, 2H, ArH), 7.55 (q, J = 7.6 Hz, 4H, ArH), 7.60
(d, J = 6.9 Hz, 2H, ArH), 7.96 (q, J = 7.1 Hz, 2H,ArH),
8.02 (d, J = 9.0 Hz, 1H,ArH), 8.26 (dd, J = 8.6 Hz, J =
1.7 Hz, 1H,ArH), 8.62 (s, 1H, ArH), 12.87 (s, 1H, NH); 13C
NMR (400 MHz, DMSO−d6) δ(ppm):118.5, 118.7, 121.4,
121.6, 121.7, 122.2, 122.8, 122.9, 122.9, 123.1, 123.3, 123.5,
123.7, 126.1, 127.7, 128.0, 130.2, 132.4, 140.5; MS (m/z):
Calcd.346.14, found 347.03 [M+1].
2.2l 4-(3,4-dimethoxyphenyl)-5-(2-chlorophenyl)-2-
(naphthalen-1-yl)-1H-imidazole (2l): Off white solid;
M.p.: 185−187 ◦C; FT-IR (KBr, cm−1
)
max: 3417.24 (N-
ν
H), 3050.83 (Ar-H), 1612.20 (C=C), 1586.16 (C=N), 786
1
2.2h 4,5-bis(4-methoxylphenyl)-2-(naphthalen-1-yl)-
(C-Cl); H NMR (500 MHz, DMSO − d6) δ (ppm): 3.31
1H-imidazole (2h): Off white solid; M.p.: 172−174 ◦C; (s, 3H, -OCH3), 3.35 (s, 3H,-OCH3), 7.14 (d, J = 8.3 Hz,
FT-IR (KBr, cm−1
)
: 3418.21 (N-H), 3046.98 (Ar- 2H, ArH), 7.25 (d, J = 7.6 Hz, 2H,ArH), 7.44 (d, J =
νmax
1
H), 1614.13 (C=C), 1574.59 (C=N); H NMR (500 MHz, 8.3 Hz, 2H, ArH), 7.50 (d, J = 7.6 Hz, 2H,ArH), 7.62 (t,
DMSO − d6) δ (ppm): 3.71 (s,3H, −CH3), 3.80 (s,3H,
J = 7.6 Hz, 2H, ArH), 7.94 (d, J = 7.6 Hz, 1H,ArH), 8.00
−CH3), 6.71 (d, J = 6.9 Hz, 1H, ArH), 6.92 (m, 4H, ArH), (d, J = 7.6 Hz,2H,ArH), 9.16 (d, J = 9.0 Hz,1H, ArH),
7.41 (t, J=8.6 Hz 1H, ArH),7.61 (m, 6H, ArH), 7.79 (d, 12.67 (s, 1H, NH); 13C NMR (400 MHz, DMSO − d6) δ