A. Fadda, H. Etman, Mohamed Y. El-Seidy
Jul 1, 2012
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0
Influential Citations
24
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
The starting (1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)carbonohydrazonoyl dicyanide (2) was used as key intermediate for the synthesis of 3-amino-2-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylazo)-[3-substituted]-1-yl-acrylonitrile derivatives (3–10). In addition, nitrile derivative 2 reacted with hydrazine hydrate or malononitrile to afford the corresponding 3,5-diaminopyrazole 11 and enaminonitrile derivative 13, respectively. On the other hand, compound 3 was subjected to react with malononitrile, acetic anhydride, triethylorthoformate, N,N-dimethylformamide (DMF)-dimethylacetal, thiourea, and hydroxylamine hydrchloride to afford antipyrine derivatives 16–21. Moreover, the reaction of enaminonitrile 3 with carbon disulfide in pyridine afforded the pyrimidine derivative 22, whereas, in NaOH/DMF followed by the addition of dimethyl sulphate afforded methyl carbonodithioate 24. The reaction of enaminonitrile derivatives 3–5 with phenylisothiocyanate afforded the thiopyrimidine derivatives 25a–c. Finally, the enaminonitrile 4 reacted with 3-(4-chloro-phenyl)-1-phenyl-propenone to afford the pyridine derivative 27. The newly synthesized compounds were characterized by elemental analyses and spectral data (IR, 13C-NMR, 1H–NMR, and MS).