T. El‐Emary, N. Al-muaikel, O. S. Moustafa
Jan 1, 2002
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0
Influential Citations
15
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Journal
Phosphorus, Sulfur, and Silicon and the Related Elements
Abstract
Treatment of 3-methyl 1-phenyl-5-amino pyrazole 1 with 4-acetyl benzene sulfonyl chloride in pyridine gave the sulfonamide 2 . Condensation of 2 with aromatic aldehydes, semicarbazide, and thiosemicarbazide furnished the f , g -unsaturated ketones 3a-c , the semicarbazone 4a and the thiosemicarbazone 4b respectively. Reaction of 3a-c with hydrazine hydrate, phenyl hydrazine, hydroxylamine, thiourea afforded the pyrazoles 5a-f , isoxazoles 6a-c , and pyrimidinethiones 7a-c . Reaction of 3a-c with malononitrile in ethanol containing piperidine provided the pyran derivatives 8a-c , while, when the reaction was carried out in boiling acetic acid in presence of ammonium acetate, the pyridine derivatives 9a-c were formed. When 4a reacted with thionyl chloride and with selenium dioxide, 1,2,3-thiadiazole and 1,2,3-selenadiazole 10 , 11 were formed respectively. Allowing 4b to react with f -halocarbonyl compounds such as phenacyl bromide, chloroacetone, 2-bromomethyl propionate, chloroacetic acid, and bromo diethylmalonate afforded the thiazolines 12a , b and thiazolidinones 13a-c respectively.