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Reaction of 5-amino-1-phenylpyrazole-4-carbonitriles with dimethyl acetylenedicarboxylate. Synthesis and structural determination of trimethyl 4,8-dioxo-1-phenyl-4,5,5a,8-tetrahydro-1H-pyrazolo[3,4-e]indolizine-5,5a,6-tricarboxylate derivatives

✍ Scribed by Yoshinori Tominaga; Noriko Yoshioka; Raymond N. Castle; Jiann-Kuan Luo; Tadashi Hata

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
570 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reaction of 5‐amino‐1‐phenylpyrazole‐4‐carbonitriles 1a‐c with dimethyl acetylenedicarboxylate in the presence of potassium carbonate in dimethyl sulfoxide gave trimethyl 4,5,5a,8‐tetrahydro‐1‐phenyl‐4,8‐dioxo‐1__H__‐pyrazolo[3,4‐e]indolizine‐5,5a,6‐tricarboxylate derivatives 3a‐c from the basic solution. The products were formed by a double Michael reaction of 1 with dimethyl acetylenedicarboxylate followed by cyclization to the cyano group. The structure of product 3a was established by X‐ray crystallography.

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