Article

Regioselective Synthesis of Polysubstituted Pyrazoles and Isoxazoles

Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, Florida 32611-7200
Department of Chemistry, University of Canterbury, Christchurch, New Zealand
J. Org. Chem., 2001, 66 (20), pp 6787–6791
DOI: 10.1021/jo0101407
Publication Date (Web): September 8, 2001
Copyright © 2001 American Chemical Society

Abstract

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A regioselective synthesis has been developed for the preparation of unsymmetrical 1,3,5-triaryl-4-alkylpyrazolines and -pyrazoles by treatment of α-benzotriazolyl-α,β-unsaturated ketones with monosubstituted hydrazines followed by alkylation at the 4-position of the pyrazoline ring. Reaction of α-benzotriazolyl-α,β-unsaturated ketones with hydroxylamine gives 3,5-disubstituted isoxazoles regioselectively.

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Article Views: 1,455 Times
Received 5 February 2001
Published online 8 September 2001
Published in print 1 October 2001
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