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Conjugation‐Driven Cascade Approach to Enantiopure Pyrano‐Fused 1,5‐Benzodiazepines by Tandem Condensation/[3,3]‐Sigmatropic Rearrangement/Aza‐Michael Addition–Elimination
Author(s) -
Husain Irfan,
Saquib Mohammad,
Shaw Arun K.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201632
Subject(s) - chemistry , enantiopure drug , sigmatropic reaction , cascade reaction , glucal , tandem , tricyclic , amine gas treating , conjugated system , combinatorial chemistry , pericyclic reaction , cascade , stereochemistry , computational chemistry , organic chemistry , enantioselective synthesis , catalysis , materials science , polymer , chromatography , composite material
Sugar‐based Morita–Baylis–Hillman (MBH) acetates easily obtained from commercially available D ‐glucal underwent rapid reaction with 1,2‐benzenediamines to give, in good yields, a series of enantiomerically pure tricyclic pyrano‐fused 1,5‐benzodiazepines with multiple points of diversity, which could serve as potential drug scaffolds. The driving force behind this reaction seemed to be the high stability associated with the conjugated tricyclic system. The reaction involved an unprecedented amine–carbonyl condensation/[3,3]‐sigmatropic rearrangement/cyclization cascade.