668
A. M. El-Saghier, E. F. Alwedi, and N. M. Fawzy
Vol 49
1660 C═N; 1H-NMR(dppm): 7.69–7.04(m, 13H, aromatic, 1H,CH)
2.20 (s, 3H, CH3).
from ethanol. m.p; 205–208ꢁC; yield: 54%; IR (KBr): 3243
(NH), 1658 (CO4), 1636 (CO3); 1H-NMR (dppm): 10.15
(2NH), 8.08–7.20 (m, 13H, aromatic 1H, CH), 2.30(s, 3H,
CH3).
(7Z)-7-(4-methylbenzylidene)-5-phenyl-2,7-dihydro-3H-imidazo
[1,5-a]imidazole(4). A mixture of compound (1a) (0.01 mol)
and ethylenediamine (0.01 mol) in dry pyridine (30 mL) was
refluxed for 10 hours, cooled and then poured onto crushed
ice –HCl with stirring. The solid obtained was filtered off
and washed with water, dried and recrystallized from
2-propanol to give brown crystals. m. p; 184–186ꢁC; yield:
Acknowledgments. The authors thank Dr. Nabil A. Saleh for
performing the biological activity testing of the synthesized
compounds, Dr. Osama Japer, Dr. Zienab Al-Kammooshy,
and Dr. Fathia Al-Ahmer for their valuable assistance in
producing NMR and IR spectra.
1
80%; IR (KBr): 1659 C═N; H-NMR(dppm): 7.74–7.08 (m, 9H,
aromatic. 1H, CH), 4.09 (t, 2H, CH2 ), 2.28 (t, 2H, CH2)2.24
(s, 3H, CH3).
(7Z)-7-benzylidene-5-phenyl-3H-imidazo[1,5-b][1,2,4]triazol-2
(7H)-ones(5a,b).
Method I.
A mixture of compounds (1a,e)
(0.01 mol) and semicarbazide (0.01 mol) in pyridine (30 mL)
was refluxed for 6 hours. The reaction mixture was cooled,
poured onto crushed ice–HCl with stirring. The solid product
was filtered off and washed with water, dried and
recrystallized from the proper solvents as yellow crystals.
REFERENCES AND NOTES
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Shinde, D. B. J Korean Chem Soc 2003, 47, 133.
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2004, 45, 425.
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1843.
[4] Beccalli, E. M.; Clerici, F.; Gelmi, M. L. Tetrahedron 1999,
55, 781.
[5] Cativila, C.; Garcia, J. I.; Mayoral, J. A.; Pires, E.; Brown, R.
Tetrahedron 1995, 51, 9217.
[6] Abdullah, M. A.; Zayed, M. E; Shawali, A. S. Indian J Chem
2001, 40B, 187.
[7] Trcek, T.; Vercek, B. J. Arkivoc 2005, (xiv), 96–101.
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Chem Soc Perkin Trans 1998, 1, 2813.
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Chem 1981, 18, 1209.
[12] Polak, M.; Vercek, B. Synth Commun 2000, 30, 2863.
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Method II.
A mixture of compound (2a) (0.01 mol) and
semicarbazide hydrochloride (0.01 mol) in pyridine (30 mL)
was refluxed for 8 hours. The reaction mixture was cooled,
poured onto crushed ice—HCl with stirring. The solid product
was filtered off and washed with water, dried and recrystallized
from 1-butanol. yield: 68 % (5a).
5a (X = CH3): m.p.; 222–224ꢁC; IR(KBr); 3342 (NH),
3045 (aromatic), 1702 (CO5). 1H-NMR(dppm): 8.38–7.18
(m, 9H, aromatic), 7.15(s, 1H, CH). 5.40 (br,1H, NH), 2.35
(s, 1H, CH3); 13C-NMR: 170.12 (CO5), 160.59 (C4), 140.47
(C3), 131.46 (C2) 128.16 (C1), 136.42, 132.33, 132.32,
131.58, 129.39, 129.36, 128.40, 126.91 (Caromatic), 21.18 (C6).
5b(X = OCH3): m.p; 190-192ꢁC; yield: 71%; IR (KBr): 3321
(NH), 3045(aroma.), 1702 (CO5); 1H-NMR(dppm): 8.46-6.80
(m, 9H, aromatic, 1H, CH).4.40 (br,1H, NH),3.85 (s, 3H,
OCH3); 13C-NMR: 170.88 (CO5), 161.80 (C4), 140.00 (C3),
131.30 (C2), 128.35 (C1), 158.25, 134.92, 131.69, 129.73,
129.53, 128.46, 127.19, 114.93 (Caromatic), 55.44 (C6).
N-[(1Z)-3-(1,3-benzothiazol-2-ylamino)-1-(4-methylphenyl)-
3-oxoprop-1-en-2-yl]benzamide(7). A mixture of compound
(1a) (0.01 mol) and 2-aminobenzothiazole (0.01 mol) in acetic
acid 930 mL) containing fused sodium acetate was refluxed for
5 hours. The solid product was filtered off and recrystallized
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet