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 language | English |
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Pages (from-to) | 11827-11834 |
Number of pages | 8 |
Journal | Tetrahedron |
Volume | 53 |
Issue number | 34 |
Publication status | Published - 25 Aug 1997 |
Keywords
- ALKALOIDS