Stereochemistry of N-Benzoyl-5-substituted-1-benzazepines Revisited: Synthesis of the Conformationally Biased Derivatives and Revision of the Reported Structure

Hidetsugu Tabata; Tetsuya Yoneda; Tomohiko Tasaka; Shigekazu Ito; Tetsuta Oshitari; Hideyo Takahashi; Hideaki Natsugari

doi:10.1021/acs.joc.5b02900

Stereochemistry of N-Benzoyl-5-substituted-1-benzazepines Revisited: Synthesis of the Conformationally Biased Derivatives and Revision of the Reported Structure

J Org Chem. 2016 Apr 15;81(8):3136-48. doi: 10.1021/acs.joc.5b02900. Epub 2016 Mar 29.

Authors

Hidetsugu Tabata¹, Tetsuya Yoneda¹, Tomohiko Tasaka², Shigekazu Ito³, Tetsuta Oshitari¹, Hideyo Takahashi¹, Hideaki Natsugari¹

Affiliations

¹ Faculty of Pharma Sciences, Teikyo University , 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan.
² Affinity Science Corporation , 1-11-1 Nishigotanda, Shinagawa-ku, Tokyo 141-0031, Japan.
³ Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology , Meguro-ku, Tokyo 152-8552, Japan.

PMID: 26999077
DOI: 10.1021/acs.joc.5b02900

Abstract

The syn (aR*,5R*) and anti (aS*,5R*) diastereomers of N-benzoyl-C5-substituted-1-benzazepines originating in the chiralities at C5 and the Ar-N(C═O) axis were first stereoselectively synthesized by biasing the conformation with a substituent at C6 and C9, respectively. Detailed examination of the stereochemistry (i.e., conformation and configuration) of these N-benzoyl-1-benzazepines by X-ray crystallographic analysis, VT NMR, and DFT calculations revealed new physicochemical aspects of these heterocycles including revision of the stereochemistry previously reported.

Publication types

Research Support, Non-U.S. Gov't