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A convenient synthesis of 8-substituted indolizines as precursors to 5-substituted cycl{3.2.2}azine derivatives

✍ Scribed by Jonathan O. Smith; Braja K. Mandal

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

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✦ Synopsis

Abstract

The synthesis of 8‐substituted indolizines is described via a two step process in which a 1,4‐diketone, containing a rerf‐butyl group, is cyclocondensed with a trialkylsilyl protected pyrrole to provide 5,8‐disubstituted indolizines in higher yields than the identical reaction with unprotected pyrrole. Cleavage of the tert‐butyl group from the indolizine 5‐position, by treatment with 85% phosphoric acid, provides 8‐substituted indolizines in good yields. Treatment of 8‐substituted indolizines with dimethyl acetylenedicarboxylate, in the presence of palladium‐on‐carbon, provides novel 5‐substituted cycl{3.2.2) derivatives.

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