Eco-friendly solvent-free synthesis of thiazolylpyrazole derivatives |
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Authors: | Samir Bondock Hossam El-Azap Ez-Eldin M. Kandeel Mohamed A. Metwally |
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Affiliation: | (1) Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, Egypt |
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Abstract: | Highly versatile ethyl 3-thiosemicarbazidobutanoate was ball-milled with phenacyl bromide to afford the corresponding ethyl 3-[(4-phenyl-2-thiazolyl)hydrazono]butanoate which underwent heterocyclization by heating in ethanolic sodium acetate to give thiazolylpyrazolone that coupled chemoselectively with aromatic diazonium salts to furnish arylhydrazonothiazolylpyrazoles. Vilsmeier-Haack reaction of ethyl 3-thiosemicarbazidobutanoate furnished selectively thiazolylpyrazole. A series of pyrazolylthiosemicarbazones were synthesized by solid-state technique which allowed waste-free production. The reaction of pyrazolylthiosemicarbazones with phenacyl bromide afforded the corresponding 2-(arylidenehydrazino)-4-phenylthiazoles in quantitative yields. Correspondence: Samir Bondock, Department of Chemistry, Faculty of Science, Mansoura University, ET-31556 Mansoura, Egypt. |
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Keywords: | Thiazole Pyrazole Thiosemicarbazide Ball-milling. |
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