T. A. Farghaly et al.
University, Giza, Egypt. Antibacterial activities were car-
ried out at the Regional Center for Mycology and Bio-
technology at Al-Azhar University, Cairo, Egypt.
Anal. Calcd. for C22H17ClN4O (388.86) C, 67.95; H, 4.41;
N, 14.41. Found: C, 67.69; H, 4.26; N, 14.35 %.
2-[(2-Chlorophenylmethylene)hydrazono]-4,4-diphenyl-
1H-imidazol-5(4H)-one (3d)
Preparation of hydrazones 3a–n
A mixture of hydrazine 1 (2.5 mmol) and the appropriate
aldehyde 2 (2.5 mmol) in acetic acid (20 mL) and few
drops of conc. hydrochloric acid (&1 mL) was heated
under reflux for 3 h. The reaction mixture was then cooled
and diluted with water. The so-formed solid product was
then collected by filtration, dried and recrystallized from
the proper solvent to afford the corresponding hydrazones
3a–n.
White solid (76 %) mp. 204–206 °C (EtOH) 1H NMR
(DMSO-d6) d ppm: 3.59 (br s, 1H, NH), 7.19–7.78 (m,
14H, ArH), 8.15 (s, 1H, =CH), 9.20 (s, 1H, NH). IR m
cm-1: 3,444, 3,163 (2NH), 1,755 cm-1. Ms m/z (%) 390
(M??2, 10), 389 (M??1, 11), 388 (M?, 34), 247 (57), 182
(36), 180 (34), 165 (55), 138 (26), 115 (26), 111 (21), 104
(60), 89 (68), 78 (45), 77 (100). Anal. Calcd. for
C22H17ClN4O (388.86) C, 67.95; H, 4.41; N, 14.41. Found:
C, 67.69; H, 4.26; N, 14.35 %.
4,4-Diphenyl-2-[(phenylmethylene)hydrazono]-1H-
imidazol-5(4H)-one (3a) (Kottke and Kuhmstedt 1978)
2-[(4-Bromophenylmethylene)hydrazono]-4,4-diphenyl-
1H-imidazol-5(4H)-one (3e)
¨
White solid (81 %) mp. 240–242 °C (EtOH) 1H NMR
(DMSO-d6) d ppm: 3.89 (br s, 1H, NH), 7.29–7.87 (m,
15H, ArH), 8.20 (s, 1H, =CH), 9.33 (s, 1H, NH). IR m
cm-1: 3,341, 3,150 (2NH), 1,735 (CO) cm-1. Ms m/z (%)
355 (M??1, 9), 354 (M?, 34), 249 (24), 248 (100), 182
(25), 165 (28), 106 (53), 104 (71), 90 (37), 77 (78). Anal.
Calcd. for C22H18N4O (354.41) C, 74.56; H, 5.12; N,
15.81. Found: C, 74.29; H, 5.08; N, 15.74 %.
White solid (83 %) mp. 238–240 °C (EtOH) 1H NMR
(DMSO-d6) d ppm: 3.81 (br s, 1H, NH), 7.05 (d, J = 8 Hz,
2H, Ar–H), 7.14–7.52 (m, 10H, Ar–H), 8.01 (d, J = 8 Hz,
2H, Ar–H), 8.23 (s, 1H, = CH), 9.781 (s, 1H, NH). IR m
cm-1: 3,405, 3,215 (2NH), 1,742 (CO) cm-1. Ms m/z (%)
435 (M??2, 5), 434 (M??1, 14), 433 (M?, 10), 432 (15),
248 (100), 182 (18), 165 (25), 104 (45), 77 (38). Anal.
Calcd. for C22H17BrN4O (433.31) C, 60.98; H, 3.95; N,
12.93. Found: C, 60.78; H, 3.86; N, 12.91 %.
4,4-Diphenyl-2-[(4-methylphenylmethylene)hydrazono]-
1H-imidazol-5(4H)-one (3b)
4,4-Diphenyl-2-[(2-hydroxyphenylmethylene)hydrazono]-
1H-imidazol-5(4H)-one (3f) (Kottke and Kuhmstedt 1978)
White solid (85 %) mp. 244–246 °C (EtOH) 1H NMR
(DMSO-d6) d ppm: 2.33 (s, 3H, CH3), 3.57 (br s, 1H, NH),
7.22 (d, J = 8 Hz, 2H, Ar–H), 7.31-7.41 (m, 10H, Ar–H),
7.76 (d, J = 8 Hz, 2H, Ar–H), 8.17 (s, 1H, = CH), 9.51 (s,
1H, NH). IR m cm-1: 3,225, 3,210 (2NH), 1,745 (CO)
cm-1. Ms m/z (%) 369 (M??1, 24), 368 (M?, 72), 367
(23), 248 (69), 180 (31), 165 (31), 120 (63), 118 (48), 104
(100), 91 (38), 88 (33), 77 (83). Anal. Calcd. for
C23H20N4O (368.44) C, 74.98; H, 5.47; N, 15.21. Found:
C, 74.85; H, 5.38; N, 15.14 %.
¨
1
White solid (78 %) mp. 216–218 °C (Dioxane) H NMR
(DMSO-d6) d ppm: 3.65 (br s, 1H, NH), 6.99–7.95 (m,
14H, ArH), 8.23 (s, 1H, =CH), 9.39 (s, 1H, NH), 13.50 (s,
1H, OH). IR m cm-1: br 3,200, 3,166 (2NH and OH), 1,755
(CO) cm-1. Ms m/z (%) 371 (M??1, 47), 370 (M?, 38),
248 (47), 182 (38), 165 (88), 122 (59), 115 (41), 105 (44),
103 (31), 77 (91). Anal. Calcd. for C22H18N4O2 (370.41) C,
71.34; H, 4.90; N, 15.13. Found: C, 71.25; H, 5.01; N,
15.10 %.
2-[(4-Chlorophenylmethylene)hydrazono]-4,4-diphenyl-
1H-imidazol-5(4H)-one (3c) (Kottke and Kuhmstedt 1978)
4,4-Diphenyl-2-[(3-hydroxyphenylmethylene)hydrazono]-
1H-imidazol-5(4H)-one (3g)
¨
1
White solid (79 %) mp. 280–282 °C (Dioxane) H NMR
(DMSO-d6) d ppm: 3.80 (br s, 1H, NH), 7.21 (d, J = 8 Hz,
2H, Ar–H), 7.29–7.58 (m, 10H, Ar–H), 7.85 (d, J = 8 Hz,
2H, Ar–H), 8.20 (s, 1H, =CH), 9.61 (s, 1H, NH). IR m
cm-1: 3,250, 3,163 (2NH), 1,747 (CO) cm-1. Ms m/z (%)
390 (M??2, 6), 389 (M??1, 2), 388 (M?, 17), 387 (32),
248 (100), 247 (57), 207 (28), 182 (42), 180 (51), 165 (49),
139 (47), 138 (26), 111 (32), 90 (21), 77 (64), 76 (89).
White solid (74 %) mp. 208–210 °C (EtOH) 1H NMR
(DMSO-d6) d ppm: 3.78 (br s, 1H, NH), 7.08–7.77 (m,
14H, ArH), 8.05 (s, 1H, =CH), 9.48 (s, 1H, NH), 14.26 (s,
1H, OH). IR m cm-1: br 3,225, 3,154 (2NH and OH), 1,759
(CO) cm-1. Ms m/z (%) 371 (M??1, 12), 370 (M?, 35),
248 (17), 181 (42), 180 (56), 165 (68), 142 (24), 141 (68),
138 (90), 77 (95). Anal. Calcd. for C22H18N4O2 (370.41) C,
123