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

Abstract

A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2-a]pyridin-3-yl)alkane-1,2-diones (3) in good yields (32-88%) from 2-phenylimidazo[1,2-a]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-a]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.