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

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• 作者：Hidetsugu Tabata ; Tetsuya Yoneda ; Tomohiko Tasaka ; Shigekazu Ito ; Tetsuta Oshitari ; Hideyo Takahashi ; Hideaki Natsugari
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：April 15, 2016
• 年：2016
• 卷：81
• 期：8
• 页码：3136-3148
• 全文大小：649K
• 年卷期：0
• ISSN：1520-6904

文摘

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.