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Communication | Regular issue | Vol 3, No. 8, 1975, pp.615-618
Published online, 1st January, 1970
DOI: 10.3987/R-1975-08-0615
Indolizine Derivatives. IV. Evidence for a Disproportnation Dehydrogenation Mechanism in the Perkin Reaction of 2-Pyridinecarbaldehyde in the Presence of α,β-Unsaturated Carbonyl Compounds to Give 1-Acylpyrrolo[2,1,5-cd]indolizines

Esko Pohjala*

*Department of Chemistry, Technical University of Helsinki, P.O. Box 6100, FIN-02150 HUT Espoo, Finland

Abstract

In the Perkin reaction of 2-pyridinecarbaldehyde (1) with 3-buten-2-one (2) and Ac2O/KOAc the normal Perkin reaction product, acetic 3-(2-pyridyl)acrylic anhydride (3), disproportionates. The reduction products include 3-indolizinyl acetate (4), which with 2 cyclizes to 1-(1,2-dihydro-1-pyrrolo[2,1,5-cd]ndolizinyl)ethanone (5). Dehydrogenation of 5 then affords 1-(1-pyrrolo[2,1,5-cd]indolizinyl)ethanone (6).