848 Medicinal Chemistry, 2012, Vol. 8, No. 5
Zeb et al.
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-nitrobenzoate
(10)
2-(2-Methyl-5-nitro-1H-imidazol-1-yl) ethyl 4-
flourobenzoate (16) [22]
Yield: 86%; Rf.: 0.49 (EtOAc/hexane 7:3); IR (KBr,
cm-1): 3327, 3927, 1714 (C=O), 1624, 1525, 1352, 1271,
1186, 821, 715; 1H NMR: (300 MHz, CDCl3): ꢀ 8.28 (d, 2H,
J3',2'/5',6' = 8.7 Hz, H-3'/H-5'), 8.08 (d, 2H, J2',3'/6',5' = 9.0 Hz,
H-2'/H-6'), 7.96 (s, 1H, H-4), 4.73 (br.s, 4H, 2 x CH2), 2.48
(s, 3H, CH3); EI MS m/z (rel. abund. %): 320 (M+, 16), 274
(52), 194 (88), 150 (100), 56(34).
Yield: 85%; Rf.: 0.42 (EtOAc/hexane 7:3); IR (KBr,
cm-1): 3423, 2923, 3099, 1720 (C=O), 1600, 1517, 1456,
1363, 1259, 1182, 1151, 1110, 864, 825, 767; 1H NMR: (400
MHz, CDCl3): ꢀ 7.96 (s, 1H, H-4), 7.91 (m, 2H, H-3'/H-5'),
7.09 (t, 2H, J2',3'/6',5' = 8.4 Hz, H-2'/H-6'), 4.68 (m, 4H, 2 x
CH2), 2.46 (s, 3H, CH3); EI MS m/z (rel. abund. %): 293
(M+, 5), 167 (30), 123 (100), 82 (52).
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-
chlorobenzoate (11)
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-iodobenzoate
(17)
Yield: 73%; Rf.: 0.56 (EtOAc/hexane 7:3); IR (KBr,
cm-1): 3131, 2933, 1730 (C=O), 1592, 1532, 1470, 1363,
1292, 1249, 1190, 1052, 748; H NMR: (300 MHz, CDCl3):
Yield: 82%; Rf.: 0.57 (EtOAc/hexane 7:3); IR (KBr,
cm-1): 3325, 2927, 1732 (C=O), 1625, 1533, 1473, 1361,
1253, 1190, 744; H NMR: (400 MHz, CDCl3): ꢀ 7.98 (dd,
1
1
ꢀ 7.96 (s, 1H, H-4), 7.66 (d, 1H, J6',5' = 7.5 Hz, H-6'), 7.43
(m, 2H, H-3'/H-4'), 7.30 (m, 1H, H-5'), 4.68 (m, 4H, 2 x
CH2), 2.46 (s, 3H, CH3); EI MS m/z (rel. abund. %): 309
(M+, 10), 263 (15), 183 (27), 139 (100), 57 (13).
1H, J6',4' = 0.8 Hz, J6',5' = 7.6 Hz, H-6'), 7.97 (s, 1H, H-4),
7.61 (dd, 1H, J3',5' = 1.6 Hz, J3',4' = 8.0 Hz, H-3'), 7.38 (td,
1H, J4',6' = 1.2 Hz, J4'/3',5' = 7.6 Hz, H-4'), 7.16 (td, 1H, J5',3'
=
1.2 Hz, J5'/4',6' = 7.6 Hz, H-5'), 4.69 (m, 4H, 2 x CH2), 2.46 (s,
3H, CH3); EI MS m/z (rel. abund. %): 401 (M+, 66), 355
(75), 274 (75), 231 (100), 84 (67).
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-
chlorobenzoate (12)
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-vinylbenzoate
(18)
Yield: 90%; Rf.: 0.52 (EtOAc/hexane 7:3); IR (KBr,
cm-1): 3325, 2927, 1732 (C=O), 1625, 1533, 1473, 1361,
1253, 1190, 744; H NMR: (300 MHz, CDCl3): ꢀ 7.96 (s,
1
Yield: 80%; Rf.: 0.49 (EtOAc/hexane 7:3); IR (KBr,
cm-1): 2947, 1720 (C=O), 1606, 1529, 1467, 1429, 1361,
1H, H-4), 7.89 (s, 1H, H-2'), 7.77 (d, 1H, J6',5' = 7.73 Hz, H-
1
1269, 1186, 1101, 862, 781, 713; H NMR: (300 MHz,
6'), 7.54 (d, 1H, J4',5' = 7.82 Hz, H-4'), 7.37 (t, 1H, J5'/4',6'
=
CDCl3): ꢀ 7.96 (s, 1H, H-4), 7.85 (d, 2H, J2',3'/6',5' = 8.4 Hz,
H-2'/H-6'), 7.43 (d, 2H, J3',2'/5',6' = 8.4 Hz, H-3'/H-5'), 6.72 (m,
1H, =CH), 5.85 (d, 1H, Jtrans-H = 17.7 Hz, trans H-2''), 5.38
(d, 1H, Jcis-H = 10.8 Hz, cis H-2''), 4.68 (m, 4H, 2 x CH2),
2.46 (s, 3H, CH3); EI MS m/z (rel. abund. %): 301 (M+, 5),
255 (18), 131 (100), 103 (42), 77 (41).
7.85 Hz, H-5'), 4.68 (m, 4H, 2 x CH2), 2.47 (s, 3H, CH3); EI
MS m/z (rel. abund. %): 309 (M+, 4), 263 (13), 139 (100),
111 (33).
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-
chlorobenzoate (13)
Yield: 70%; Rf.: 0.57 (EtOAc/hexane 7:3); IR (KBr,
cm-1): 3325, 2927, 1732 (C=O), 1625, 1533, 1473, 1361,
1253, 1190, 744; H NMR: (300 MHz, CDCl3): ꢀ 7.96 (s,
2-(2-Methyl-5-nitro-1H-imidazol-1-yl) ethyl 4-
(bromomethyl)benzoate (19)
1
1H, H-4), 7.84 (d, 2H, J2',3'/6',5' = 8.4 Hz, H-2'/H-6'), 7.40 (d,
2H, J3',2'/5',6' = 8.7 Hz, H-3'/H-5'), 4.67 (m, 4H, 2 x CH2), 2.46
(s, 3H, CH3); EI MS m/z (rel. abund. %): 309 (M+, 11), 263
(51), 183 (55), 139 (100), 111 (35).
Yield: 81%; Rf.: 0.42 (EtOAc/hexane 7:3); IR (KBr,
cm-1): 3435, 2925, 3099, 1712 (C=O), 1620, 1531, 1469,
1367, 1267, 1188, 1105, 700, 599; H NMR: (400 MHz,
CDCl3): ꢀ 7.96 (s, 1H, H-4), 7.87 (d, 2H, J2',3'/6',5' = 8.4 Hz,
H-2'/H-6'), 7.44 (d, 2H, J3',2'/5',6' = 8.0 Hz, H-3'/H-5'), 4.68 (m,
4H, 2 x CH2), 4.47 (s, 2H, CH2Ph), 2.46 (s, 3H, CH3); EI MS
m/z (rel. abund. %): 369 (M+, 7), 367 (5), 323 (42), 321 (38),
199 (100), 197 (99), 118 (57).
1
2-(2-Methyl-5-nitro-1H-imidazol-1-yl) ethyl 2-
flourobenzoate (14)
Yield: 74%; Rf.: 0.56 (EtOAc/hexane 7:3); IR (KBr,
cm-1): , 3020, 2934, 2856, 1724 (C=O), 1651, 1613, 1533,
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-
methoxybenzoate (20)
1
1458, 1364, 1296, 1254, 1191, 1127,1085, 760; H NMR:
(300 MHz, CDCl3): ꢀ 7.96 (s, 1H, H-4), 7.82 (td, 1H, J6'/2',4'
1.5 Hz, J6',5' = 7.5 Hz, H-6'), 7.52 (m, 1H, H-4'), 7.19 (t, 1H,
5'/4',6' = 7.8 Hz, H-5'), 7.11 (t, 1H, J3'/2',4' = 9.0 Hz, H-3'), 4.68
=
Yield: 71%; Rf.: 0.39 (EtOAc/hexane 7:3); IR (KBr,
cm-1): 3741, 2966, 1726 (C=O), 1706, 1529, 1465, 1431,
J
1
1361, 1298, 1253, 1188, 1082, 759; H NMR: (300 MHz,
(m, 4H, 2 x CH2), 2.46 (s, 3H, CH3); EI MS m/z (rel. abund.
%): 293 (M+, 4), 167 (30), 122 (100), 82 (52).
CDCl3): ꢀ 7.96 (s, 1H, H-4), 7.65 (dd, 1H, J6',5' = 8.1 Hz, J6',4'
= 1.8 Hz, H-6'), 7.46 (dt, 1H, J4'/5',3' = 8.7 Hz, J4',6' = 1.8 Hz,
H-4'), 6.95 (m, 2H, H-3'/H-5'), 4.67 (m, 4H, 2 x CH2), 2.46
(s, 3H, CH3); EI MS m/z (rel. abund. %): 305 (M+, 5), 148
(13), 132 (100), 77 (41).
2-(2-Methyl-5-nitro-1H-imidazol-1-yl) ethyl 3-
flourobenzoate (15)
Yield: 75%; Rf.: 0.42 (EtOAc/hexane 7:3); IR (KBr,
cm-1): 3326, 2925, 1725 (C=O), 1625, 1530, 1467, 1362,
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 2,3-
diflourobenzoate (21)
1
1267, 1191, 755; H NMR: (300 MHz, CDCl3): ꢀ 7.96 (s,
1H, H-4), 7.69 (d, 1H, J6',5' = 7.8 Hz, H-6'), 7.59 (d, 1H, J4',5'
= 8.7 Hz, H-4'), 7.41 (m, 1H, H-5'), 7.28 (m, 1H, H-2'), 4.69
(m, 4H, 2 x CH2), 2.47 (s, 3H, CH3); EI MS m/z (rel. abund.
%): 293 (M+, 17), 247 (48), 167 (72), 123 (100), 95 (49).
Yield: 79%; Rf.: 0.47 (EtOAc/hexane 7:3); IR (KBr,
cm-1): 3131, 2975, 1729 (C=O), 15 31, 1428, 1363, 1265,
1190, 1147, 1038, 828, 755; 1H NMR: (300 MHz, CDCl3): ꢀ