Route to Functionalized Tetrahydrobenzo[]azepines via ReO-Mediated Intramolecular Friedel-Crafts Reaction.

J Org Chem

Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Materials Chemistry and Service Failure, and School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, China.

Published: February 2024

We describe a ReO-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.

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http://dx.doi.org/10.1021/acs.joc.3c01977DOI Listing

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