Expedient access to α,β-difunctionalized azepenes using α-halo eneformamides: application to the one-pot synthesis of 2-benzazepanes†,10.1039/C4OB02183E

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Expedient access to α,β-difunctionalized azepenes using α-halo eneformamides: application to the one-pot synthesis of 2-benzazepanes†

Daniel P. Bassler,Laura Spence,Amir Alwali,Oliver Beale,Timothy K. Beng

Organic & Biomolecular Chemistry Pub Date : 01/02/2015 00:00:00 , DOI:10.1039/C4OB02183E

Abstract

The regioselective synthesis of α,β-difunctionalized (alkenyl, aryl, sulfonyl, allyl, or alkynyl) azepenes has been accomplished through α-halo eneformamides. A successful implementation of the vicinal functionalization strategy has led to a one-pot synthesis of 2-benzazepanes whose benzenoid portion is highly functionalized.