A highly efficient and facile one pot synthesis of novel 1-glycopyranosyl-4-biaryl butenone derivatives

Abstract

A facile and efficient methodology, comprised of a domino reaction, a Suzuki-Miyaura coupling reaction followed by an aldol condensation has been developed to synthesize novel 1-glycopyranosyl-4-biaryl butenone derivatives in a one-pot fashion. The reaction of C-glycosides 1-C-(β-D-glucosyl)propan-2-one, 1-C-(β-D-mannosyl)propan-2-one, 1-C-(β-D-galactosyl)propan-2-one, 1-C-(β-D-lactosyl)propan-2-one with 5-bromothiophene-2-carboxaldehyde or 4-bromobenzaldehyde and different boronic acids in the presence of Pd(II)-catalyst and a base in methanol at room temperature produced various chalcone type biphenyl C-glycosides in 75–85% yields.