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Note | Regular issue | Vol 57, No. 7, 2002, pp.1303-1311
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9494
Pyrrolizine and Indolizine Derivatives from 1,6-Dioxo-2,4-diene by Inter- and Intramolecular Ring Closure

Chi Wi Ong,* Ming Chih Lai, Jing Jyh Jan, and Yu An Chang

*Department of Chemistry, National Sun Yat Sen University, Kaohsiung, 804, Taiwan, R.O.C.

Abstract

A variety of 1-amino-alkyl esters and nitriles react with 1,6-dioxo-2,4-diene to give pyrrole derivatives in good yield. Mild basic conditions facilitate the further intramoleular Dieckmann or Thorpe like condensation giving pyrrolizine and indolizine derivatives. These reactions provide simple, two step sequence to pyrrolizine and indolizine derivatives with control of product dictated by the base used for the condensation reaction.