Route to Functionalized Tetrahydrobenzo[ d]azepines via Re2O7-Mediated Intramolecular Friedel-Crafts Reaction

J Org Chem. 2024 Feb 2;89(3):2001-2008. doi: 10.1021/acs.joc.3c01977. Epub 2024 Jan 22.

Abstract

We describe a Re2O7-mediated intramolecular dehydrative Friedel-Crafts reaction for the efficient synthesis of various benzo-fused heterocycles such as benzazepines and benzazocines. This process is characterized by a broad substrate scope, mild reaction conditions, high efficiency, and high atom economy. The potential application of this methodology was exemplified by the facile preparation of a NMDA antagonist as well as a key intermediate en route to SKF 38393.