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Full Paper
Conjugation-Driven Cascade Approach to Enantiopure Pyrano-Fused 1,5-Benzodiazepines by Tandem Condensation/[3,3]-Sigmatropic Rearrangement/Aza-Michael Addition–Elimination
Article first published online: 1 MAR 2013
DOI: 10.1002/ejoc.201201632
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Husain, I., Saquib, M. and Shaw, A. K. (2013), Conjugation-Driven Cascade Approach to Enantiopure Pyrano-Fused 1,5-Benzodiazepines by Tandem Condensation/[3,3]-Sigmatropic Rearrangement/Aza-Michael Addition–Elimination. Eur. J. Org. Chem., 2013: 2194–2200. doi: 10.1002/ejoc.201201632
Publication History
- Issue published online: 3 APR 2013
- Article first published online: 1 MAR 2013
- Manuscript Received: 4 DEC 2012
Keywords:
- Medicinal chemistry;
- Nitrogen heterocycles;
- Oxygen heterocycles;
- Molecular diversity;
- Sigmatropic rearrangement
Abstract
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.