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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Indolizines. IV. Reductive cleavage of acyl groups from acetylindolizines. C-Protonation and fragmentation of Indolizine-3-carbinols

I Dainis

Australian Journal of Chemistry 25(9) 2013 - 2020
Published: 1972

Abstract

Sodium borohydride in ethanol has effected cleavage of 3-acetylindolizines to indolizines in those cases where the intermediate 3-carbinols are readily protonated at C3. Reduction of 3-acetyl-2-methylindolizine in EtOD has demonstrated that fragmentation proceeds via C-protonation, and has also provided a selective method for the 3-deuteration of reactive indolizines. 1-Acetyl- and 1,3-diacetyl-indolizines gave unstable product mixtures on reduction excepting the one case where the product carbinol was stabilized by a resistant, electron-withdrawing 3-substituent. 3-Ethoxyoarbonyl groups were not affected.

https://doi.org/10.1071/CH9722013

© CSIRO 1972

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