Gold-catalyzed oxidation of terminal alkynes to glyoxals and their reactions with 2-phenylimidazo[1,2-]pyridines: one-pot synthesis of 1,2-diones.

Org Biomol Chem

CAS Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Research Center for Marine Microbes, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, China.

Published: October 2021

A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2-]pyridin-3-yl)alkane-1,2-diones (3) in good yields (32-88%) from 2-phenylimidazo[1,2-]pyridines (1) and terminal alkynes (2) has been established with a wide range of substrate scope. A tandem reaction sequence containing gold-catalyzed double oxidations of terminal alkynes to generate glyoxals, nucleophilic addition of 2-phenylimidazo[1,2-]pyridines to glyoxals to yield α-hydroxyl ketones, and oxygenation of the α-hydroxyl ketones to afford the final products 3 under air atmosphere is involved in this method. Simple operation, mild reaction conditions, and widely available substrates make this strategy more affordable.

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http://dx.doi.org/10.1039/d1ob01507aDOI Listing

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