Abstract:
Sugar based Morita-Baylis-Hillman (MBH) acetates easily obtained from commercially available D-glucal underwent rapid reaction with different o-phenylenediamines to afford a series of novel enantiomerically pure tricyclic pyrano-fused 1,5-benzodiazepines possessing multiple points of diversity which could serve as potential drug scaffolds in good yields. The driving force behind this reaction seemed to be the high stability associated with conjugated tricyclic system and involved an unprecedented amine-carbonyl condensation-[3,3] sigmatropic rearrangement-cyclization cascade.
