Facile synthesis of novel 3H-1,5-benzodiazepine-derived aryl C-glycosides by coupling of sugar alkynes, acyl chlorides and 1, 2-phenylenediamine

Abstract

Novel 3H-1,5-benzodiazepine-derived aryl C-glycosides were synthesized in good to excellent yields by the coupling of structurally diverse terminal sugar alkynes, aroyl chlorides and 1, 2-phenylenediamine. The protocol is general, mild and efficient. It was suitable for various terminal sugar alkynes and aroyl chlorides, with 37 selected examples. The sugar substrates include pyranosides, furanosides, and acyclic sugars with sensitive and bulky protecting groups. The aroyl chlorides contain electron-donating, electron-withdrawing and electron-neutral substituents.