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Convenient one-pot syntheses of pyrazoles from imines, a vilsmeier type reagent and hydrazine

✍ Scribed by Alan R. Katritzky; Anna Denisenko; Sergey N. Denisenko; Michael Arend

Book ID
102343357
Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
370 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A simple one‐pot procedure for the regioselective synthesis of pyrazoles from readily available starting materials is described. Vilsmeier type reagent 1 reacts with imines 10 (via the corresponding tautomeric secondary enamines) in tetrahydrofuran to give enaminoimine hydrochlorides 11. Nonsymmetrical imines generally react preferentially with 1 at the sterically less hindered α‐position. The enaminoimine hydrochlorides 11 are transformed in situ to the corresponding pyrazoles 12 in moderate to high yields by the addition of hydrazine.

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