Ag(I)/Au(I)-Catalyzed Domino Propargylation/Aza-Annulation to Access Coumarino[4,3-b]pyridines

Abstract

An approach for the synthesis of diversely substituted coumarino[4,3-b]pyridines (5H-[1]benzopyrano[4,3-b]pyridin-5-ones), involving the annulation of 4-aminocoumarins with propargylic alcohols, is reported. The reaction proceeds through C-3 propargylation followed by an aza-annulation in a domino manner in the presence of AgSbF₆/AuCl(PPh₃) as the catalytic system. The products can be synthesized from a broad range of propargylic alcohols, demonstrating the compatibility with different functional groups.

Key words

coumarino[4,3-b]pyridine - 5H-[1]benzopyrano[4,3-b]pyridin-5-one - propargylic alcohol - propargylation - aza-annulation - domino reaction

Publication History

Received: 05 February 2025

Accepted after revision: 26 March 2025

Accepted Manuscript online:
26 March 2025

Article published online:
14 April 2025

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