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HETEROCYCLES, Vol. 78, No. 6, 2009
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10H, H-Ar), 7.82 (s, 1H, Hc), 10.05 (s, 1H, Hb); C-NMR (300 MHz, DMSO-d6): 85.3, 98.8, 132.2,
133.1, 133.6, 133.8, 134.5, 134.7, 142.5, 145.1, 146.9, 150.5, 153.5, 157.0; Anal. Calcd for C9H10N4O2: C,
52.42; H, 4.89; N, 27.17. Found: C, 52.25; H, 4.90; N, 27.21.
(Z)-4-Amino-5-(hydroxyimino)-2-(2-hydroxyphenyl)-2,5-dihydro-1H-imidazole 3-oxide (3b): Yield
o
(85%). White solid, mp 110-112 C (decomp.); IR (KBr, cm-1): 3414, 3330 (NH2), 3268, 3182 (OH),
2760 (the ring of imidazole), 1729, 1700 (C=N), 1609, 1464 (the ring of benzene), 1369 (N=O), 1230
1
(C-N), 959, 930 (N-O); H-NMR (300 MHz, DMSO-d6): 1.06 (t, J = 6.99 Hz, 6H), 3.44 (m, 4H,),
4.36(s, 2H), 5.58 (s, 2H, 2OH), 6.25 (d, J = 1.62 Hz, 1H, Ha), 6.66 (d, J = 1.36 Hz, 1H, Ha), 6.81-6.85 (m,
4H, H-Ar), 7.02 (s, 2H, Hd), 7.12 (d, J=1.38 Hz, 1H, Hb), 7.15-7.35 (m, 4H, H-Ar), 7.95 (d, J = 1.89 Hz,
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1H, Hb), 10.16 (s, 1H, Hc), 10.23 (s, 1H, Hc); C-NMR (300 MHz, DMSO-d6): 24.0, 61.5, 81.5, 93.7,
120.8, 123.0, 124.2, 129.1, 130.6, 130.9, 132.4, 132.5, 135.4, 135.7, 143.4, 147.1, 149.8, 156.9, 160.8,
162.7; Anal. Calcd for C11H16N4O4: C, 49.25; H, 6.01; N, 20.88. Found: C, 49.17; H, 5.96; N, 21.09.
(Z)-4-Amino-5-(hydroxyimino)-2-(4-methylphenyl)-2,5-dihydro-1H-imidazole 3-oxide (3c): Yield
o
(72%). White solid, mp 182.5-184 C (decomp.); IR (KBr, cm-1): 3360, 3260 (NH2), 3190, 3097 (OH),
2880 (the ring of imidazole), 1720, 1686 (C=N), 1600, 1523, 1450 (the ring of benzene), 1360 (N=O),
1
1230 (C-N), 959, 928 (N-O); H-NMR (300 MHz, DMSO-d6): 2.32 (s, 6H, 2CH3), 5.59 (s, 1H, Ha),
5.71(s, 1H, Ha), 6.35 (s, 1H, one of Hd), 6.43 (s, 2H, Hd), 7.20-7.35 (m, 8H, H-Ar), 7.49 (s, 1H, Hb), 7.75
(s, 1H, Hb), 9.98 (s, 1H, Hc), 10.21 (s, 1H, Hc); 13C-NMR (300 MHz, DMSO-d6): 26.3, 85.2, 98.8, 132.2,
133.0, 134.1, 134.3, 139.5, 142.1, 142.2, 143.9, 144.1, 147.0, 150.6, 157.0; Anal. Calcd for C10H12N4O2:
C, 54.54; H, 5.49; N, 25.44. Found: C, 54.30; H, 5.63; N, 25.56.
(Z)-4-Amino-5-(hydroxyimino)-2-(2-methoxyphenyl)-2,5-dihydro-1H-imidazole 3-oxide (3d): White
o
solid, mp 181-182.5 C (decomp.); IR (KBr, cm-1): 3315, 3265 (NH2), 3182 (OH), 2892 (CH3), 1711,
1690 (C=N), 1604, 1494, 1469 (the ring of benzene), 1348 (N=O), 1273,1023 (Ar-O-C), 1223 (C-N), 930
1
(N-O); H-NMR (300 MHz, DMSO-d6): 3.80 (s, 3H, CH3), 5.58 (s, 2H, Ha), 6.66 (d, J = 1.97 Hz, 1H,
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Hd), 7.04 (d, J = 8.10 Hz, 2H, H-Ar), 7.21(s, 1H, Hc), 7.40 (m, 2H, H-Ar), 10.16 (s, 1H, Hb); C-NMR
(300 MHz, DMSO-d6): 61.0, 61.3, 80.8, 93.5, 116.6, 117.0, 125.7, 125.8, 130.3, 132.2, 132.6, 133.3,
135.7, 135.8, 143.1, 147.0, 150.9, 156.8, 162.5, 163.7; Anal. Calcd for C10H12N4O3: C, 50.84; H, 5.12; N,
23.72. Found: C, 50.41; H, 5.25; N, 23.45.
(Z)-4-Amino-5-(hydroxyimino)-2-(2-nitrophenyl)-2,5-dihydro-1H-imidazole 3-oxide (3e): Yellow
solid, mp 191-193 oC (decomp.); IR (KBr, cm-1): 3350, 3251 (NH2), 3180, 3106 (OH), 2880 (the ring of
imidazole), 1700, 1677 (C=N), 1600, 1530, 1471 (the ring of benzene), 1350 (N=O), 1335 (NO2), 1240
(C-N), 976, 941 (N-O); 1H-NMR (400 MHz, DMSO-d6 ): 6.51 (s, 1H, Hd), 7.52 (dd, J = 7.81, 1.30 Hz,
1H, H-Ar), 7.67 (dt, J = 8.09, 8.08, 1.40 Hz, 1H, H-Ar), 7.79 (dt, J = 7.58, 7.57, 0.93 Hz, 1H, H-Ar),
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8.03 (dd, J = 8.11, 1.06 Hz, 1H, H-Ar); C-NMR (300 MHz, DMSO-d6 ): 80.5, 94.2, 129.3, 130.2,