Synthesis 2015; 47(24): 3907-3913
DOI: 10.1055/s-0035-1560201
paper
© Georg Thieme Verlag Stuttgart · New York

Freezing the Butterfly Motion of Carbamazepine Derivatives

Yuki Kanase
Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan   Email: hide-tak@pharm.teikyo-u.ac.jp
,
Mai Kuniyoshi
Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan   Email: hide-tak@pharm.teikyo-u.ac.jp
,
Hidetsugu Tabata
Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan   Email: hide-tak@pharm.teikyo-u.ac.jp
,
Yuka Takahashi
Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan   Email: hide-tak@pharm.teikyo-u.ac.jp
,
Susumu Kayama
Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan   Email: hide-tak@pharm.teikyo-u.ac.jp
,
Shintaro Wakamatsu
Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan   Email: hide-tak@pharm.teikyo-u.ac.jp
,
Tetsuta Oshitari
Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan   Email: hide-tak@pharm.teikyo-u.ac.jp
,
Hideaki Natsugari
Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan   Email: hide-tak@pharm.teikyo-u.ac.jp
,
Hideyo Takahashi*
Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan   Email: hide-tak@pharm.teikyo-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 23 July 2015

Accepted after revision: 04 August 2015

Publication Date:
09 September 2015 (online)


Abstract

Atropisomeric properties were found in carbamazepine derivatives. The atropisomers of N-acyl and N-thiocarbamoyl derivatives of carbamazepine were isolated, with high stereochemical stability. It has been elucidated that the rotation about the N–C1′ axis around the outer amide N–(C=O) does not coordinate with the rotation of the butterfly-like motion.

Supporting Information

 
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