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Paper | Special issue | Vol 99, No. 1, 2019, pp.566-581
Published online, 6th November, 2018
DOI: 10.3987/COM-18-S(F)55
Atropisomeric and Conformational Properties of 6N-Benzoyl- and 6N-p-Tosyl-1,6-Benzodiazocines: Comparison with Those of 1,5-Benzodiazepines

Hidetsugu Tabata,* Kazuya Murai, Kaoru Funaki, Chihiro Takemae, Tomohiko Tasaka, Tetsuta Oshitari, Hideyo Takahashi,* and Hideaki Natsugari*

*Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan

Abstract

The atropisomeric and conformational properties of the eight-membered 1,6-benzodiazocines (2) with 6N-benzoyl (A) and 6N-p-tosyl (B) groups were examined by comparing them with those of the seven-membered 1,5-benzodiazepine congeners (1) (A, B). The conformation (orientation) of the benzene ring in the benzoyl and tosyl groups differed depending on the ring size (7/8) and N-substituent (-CO-/-SO2-). The activation free-energy barrier to rotation of the axes in N-p-tosyl derivatives (B) was shown to be much higher than those of the benzoyl derivatives (A).