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

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 s...

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Published inJournal of organic chemistry Vol. 81; no. 8; pp. 3136 - 3148
Main Authors Tabata, Hidetsugu, Yoneda, Tetsuya, Tasaka, Tomohiko, Ito, Shigekazu, Oshitari, Tetsuta, Takahashi, Hideyo, Natsugari, Hideaki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.04.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
VASOPRESSIN RECEPTOR
ATROPISOMERISM
HETEROCYCLES
LIGANDS
RING
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Summary: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.
Bibliography:KAKEN
ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b02900