Aza-annulation of enaminones with crotonyl chloride - Formal reversal of regioselectivity.

JP Murphy, M Hadden, PJ Stevenson

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Abstract

The regiochemistry of aza-annulation of enaminones with alpha,beta-unsaturated acid chlorides bearing hydrogen atoms on the gamma-carbon is reversed when triethylamine is used as mediator. When the reaction was carried out at lower temperatures as 3-acyl beta,gamma-unsaturated compound could be isolated which cyclised to the desired product under thermal or basic conditions. The nature of this intermediate strongly suggests that a vinyl ketene is the active acylating agent. (C) 1997 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)11827-11834
Number of pages8
JournalTetrahedron
Volume53
Issue number34
Publication statusPublished - 25 Aug 1997

Keywords

  • ALKALOIDS

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