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Eco-friendly solvent-free synthesis of thiazolylpyrazole derivatives

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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.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, Egypt

    Samir Bondock, Hossam El-Azap, Ez-Eldin M. Kandeel & Mohamed A. Metwally

Authors
  1. Samir Bondock
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  2. Hossam El-Azap
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  3. Ez-Eldin M. Kandeel
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  4. Mohamed A. Metwally
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Corresponding author

Correspondence to Samir Bondock.

Additional information

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

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