Add time:08/02/2019         Source:sciencedirect.com

The regiochemistry of aza-annulation of enaminones with α,β-unsaturated acid chlorides bearing hydrogen atoms on the γ-carbon is reversed when triethylamine is used as mediator. When the reaction was carried out at lower temperatures a 3-acyl β,γ-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.

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