An efficient and unified approach for the synthesis of diversely substituted pyridines, β-carbolines, γ-carbolines and other fused azaheteroaromatics has been realized, under metal-free conditions, starting from propargylic amines and α, β–unsaturated carbonyl compounds. This unified strategy involves imine formation followed by concomitant cyclization through an allenyl intermediate to afford pyridines, β- and γ-carbolines as well as a range of fused azaheteroaromatics that include pyrrolopyridine, furopyridine, thienopyridine, benzofuropyridine, pyrrolodipyridine, benzothienopyridine, phenanthroline and benzisoquinoline, with a broad substrate scope and excellent functional group compatibility. We have achieved the formal synthesis of oxopropalines D and G on a gram-scale, in a one-pot reaction from commercially available materials (previous shortest reported route was 5 steps) and one-step synthesis of the monoterpene alkaloid, (-)-actinidine, an ant-associated iridoid. Furthermore, we prepared an analogue of oxopropaline in two steps with a 69% overall yield. This mild strategy is also suitable for functionalization of natural products or other advanced intermediates having α, β–unsaturated carbonyl functionality.

Unified strategy for the synthesis of pyridines, β- & γ-carbolines, and other fused azaheteroaromatics under mild, metal-free conditions

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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