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

Hideaki Wakamatsu; Yoshimi Sasaki; Masatoshi Kawahata; Kentaro Yamaguchi; Yuichi Yoshimura

doi:10.1055/s-0037-1609857

Synthesis, Table of Contents

Synthesis 2018; 50(17): 3467-3486
DOI: 10.1055/s-0037-1609857

paper

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

Hideaki Wakamatsu*

^aFaculty 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

^aFaculty 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

^bKagawa School of Pharmaceutical Sciences, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan

^cLaboratory of Pharmaceutical Sciences and Education, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan

,

Kentaro Yamaguchi

^bKagawa School of Pharmaceutical Sciences, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan

,

Yuichi Yoshimura*

^aFaculty 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

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Abstract

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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.

Key words

ruthenium carbene complex - ynamide - ring-closing metathesis - heterocycles - medium-sized ring

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References

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