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Reaction of Isocyanates and Isothiocyanates with Butyraldazine; Formation of 1-Substituted 2-Pyrazolines

✍ Scribed by Ludwig Zirngibl; S. W. Tam

Publisher: John Wiley and Sons
Year: 1970
Tongue: German
Weight: 647 KB
Volume: 53
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19700530744

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✦ Synopsis

Abstract

Phenyl isothiocyanate reacts with butyraldazine in presence of acidic catalysts to form a 2‐pyrazoline (IV) whereas phenyl or benzyl isocyanates under similar conditions yield a mixture of the two isomeric 2‐pyrazolines XIa and XII. On reaction with Ac~2~O, IV gave the 1‐acetyl derivative V. Reduction with LiAlH~4~ led to the corresponding pyrazolidines. Reexamination of Kost's three step preparation of a 1‐phenylthiocarbamoyl 2‐pyrazoline [19] such as X via formic acid cyclization [18] of butyraldazine revealed that his first step product was apparently a mixture of two stereoisomeric 1‐formyl‐2‐pyrazolines VIIIa and VIIIb. A mechanism for the formation of these pyrazolines is proposed.

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