One-pot synthesis of heteroaryl diketoalkynyl C-glycoside and dialkynyl di-C-glycoside analogues by three-component successive coupling reaction

Abstract

The synthesis of heteroaryl diketoalkynyl C-glycoside and dialkynyl di-C-glycoside analogues has been accomplished by successive coupling of heteroaromatics, oxalyl chloride and terminal sugar alkynes in one pot. The three-component coupling reaction catalyzed by CuI gives heteroaryl diketoalkynyl C-glycosides. The same three-component coupling in the presence of n-BuLi produces dialkynyl di-C-glycosides, and the 1:1 of molar ratio of heteroaromatics to terminal sugar alkynes affords the corresponding esters of dialkynyl di-C-glycosides. The desired products have been obtained in good to excellent yields. This sequential one-pot method is mild and efficient, suitable for different heteroaromatics and terminal sugar alkynes. The sugar alkynes include furanosides, pyranosides, and acyclic sugars. Twenty-seven examples have been given. The mechanism for the formation of the desired products has been elucidated.

Keywords: Analogue; C-glycoside; Sugar alkyne; Ynedione; di-C-Glycoside.