Synthesis of novel Glycoconjugates derived from Alkynyl heterocycles through a click approach

Accepted author version posted online: 05 Jun 2012The synthesis of a series of novel 1,4-disubstituted 1,2,3-triazole compounds bearing a D-glucose derivative and an heteroaromatic system is described. Alkylation of isatin, 3-methyl-carbazole and one tetrahydro-gamma-carboline with propargyl bromide gave their N-propargyl derivatives in good yields. These compounds further reacted with acetylated D-glucose with the azide group in position 1, to give three final products and with peracetylated 6-azido-6-deoxy-alpha-D-methylglucoside giving the corresponding derivative of tetrahydro-gamma-carboline.FCT (Fundação para a Ciência e Tecnologia) and FEDE