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Synthesis 2004(1): 26-32  
DOI: 10.1055/s-2003-44357
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Concise Synthetic Method for Sydnonyl-Substituted Pyrazoline Derivatives

Mei-Hsiu Shih*
Department of Chemical Engineering, Southern Taiwan University of Technology, Tainan 710, Taiwan, R.O.C.
Fax: +886(6)2425741; e-Mail: meihsius@mail.stut.edu.tw;
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Publication History

Received 27 August 2003
Publication Date:
03 December 2003 (online)

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Abstract

The pyrazolines have been found to have diverse applications in medicine. They are known to be potent antibiotic or antioxidizing agents. Two types of sydnonyl-substituted α,β-unsaturated ketones were synthesized by the Claisen-Schmidt condensation for the preparation of sydnonyl-substituted pyrazolines. One is the condensation of 3-(4-ethoxyphenyl)-4-formylsydnone (1) with acetone (2a) or acetophenone (2b), and the other is the condensation of 4-acetyl-3-arylsydnones 5 with various aryl aldehydes 6. Finally, 1H-pyrazoline derivatives 8 were synthesized successfully by reacting the appropriate α,β-unsaturated ketone precursors 7 with hydrazine hydrate.

Key words

sydnones - 4-acetyl-3-arylsydnones - sydnonyl-substituted α,β-unsaturated ketones - pyrazoles - sydnonyl-substituted pyrazolines