Synthesis 2018; 50(17): 3467-3486
DOI: 10.1055/s-0037-1609857
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Various Heterocycles Having a Dienamide Moiety by Ring-Closing Metathesis of Ene-ynamides

Hideaki Wakamatsu*
a  Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan   Email: hiwaka@tohoku-mpu.ac.jp   Email: yoshimura@tohoku-mpu.ac.jp
,
Yoshimi Sasaki
a  Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan   Email: hiwaka@tohoku-mpu.ac.jp   Email: yoshimura@tohoku-mpu.ac.jp
,
Masatoshi Kawahata
b  Kagawa School of Pharmaceutical Sciences, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan
c  Laboratory of Pharmaceutical Sciences and Education, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan
,
Kentaro Yamaguchi
b  Kagawa School of Pharmaceutical Sciences, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan
,
Yuichi Yoshimura*
a  Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan   Email: hiwaka@tohoku-mpu.ac.jp   Email: yoshimura@tohoku-mpu.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 23 March 2018

Accepted after revision: 23 April 2018

Publication Date:
30 May 2018 (online)

Abstract

Ring-closing metathesis (RCM) of ynamides, having alkene substituents of various lengths on the side chain, was demonstrated using the second-generation Grubbs catalyst. When the reaction of ene-ynamides was carried out in the presence of 5 mol% of the catalyst, RCM proceeded smoothly to give quinoline or isoquinoline derivatives having a dienamide unit in good yields. Furthermore, RCM of ene-ynamides, having one more carbon on the side chain, proceeded smoothly to provide seven-membered heterocycles having a dienamide component. Similarly, eight-membered heterocycles, diazocine and benzodiazocine, were also synthesized by RCM of ene-ynamides in good yields.

Supporting Information

 
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