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.
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Correspondence: Samir Bondock, Department of Chemistry, Faculty of Science, Mansoura University, ET-31556 Mansoura, Egypt.
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Bondock, S., El-Azap, H., Kandeel, EE. et al. Eco-friendly solvent-free synthesis of thiazolylpyrazole derivatives. Monatsh Chem 139, 1329–1335 (2008). https://doi.org/10.1007/s00706-008-0930-4
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DOI: https://doi.org/10.1007/s00706-008-0930-4