Efficient synthesis of glycosylated imidazo[1,2-a]pyridines via solvent catalysed Groebke-Blackburn-Bienayme reaction

Abstract

A solvent catalysed and metal catalyst-free Groebke-Blackburn-Bienayame three component reaction (GBB-3CR) has been developed for the synthesis of 2-(β-D-glycal-1-yl)-3-N-alkylamino-1-azaindolizines and 2-alkyl/aryl/heteroaryl-3-N-alkylamino-1-azaindolizines. The modified GBB reaction protocol is highly efficient, versatile, atom economic and has been performed in hexafluoroisopropanol (HFIP) without any added catalyst. The GBB-3CR showed high tolerance for a large no of substrates in term of aldehydes, differently substituted 2-aminopyridines and isocyanides without being affected by the presence of electron donating and electron withdrawing substituents at either aldehydes or 2-aminopyridines.

Keywords: GBB reaction; Glycosylated 1-azaindolizines; HFIP; Metal-free; Solvent catalysed reaction.