Catalytic Synthesis of 1H-Benzoxazolo[3,2-a]pyridin-1-ones via Formal [3 + 3] Annulations of NHC-Generated Alkynyl Acylazoliums with Benzoxazolyl Acetates and Their Photophysical Studies

Abstract

We disclose the synthesis of a tricyclic fused N-heterocycle via the NHC-catalyzed annulation of either a ynal or an alkynyl ester with readily accessible benzoxazolyl acetate. While the annulation with ynals requires an oxidant, the reaction with alkynyl esters proceeds via the direct generation of alkynyl acylazolium intermediates with an NHC. With the dearth of catalytic processes to access these 1H-benzoxazolo[3,2-a]pyridin-1-ones from simple starting materials, this method is especially important. The photophysical properties of the products have also been evaluated.