Issue 10, 2020
From the journal:

Chemical Communications

Direct synthesis of 2-arylazulenes by [8+2] cycloaddition of 2H-cyclohepta[b]furan-2-ones with silyl enol ethers†

Taku Shoji, ORCID logo *a   Shuhei Sugiyama,a   Yoshiaki Kobayashi,a   Akari Yamazaki,a   Yukino Ariga,a   Ryuzi Katoh, ORCID logo b   Hiroki Wakui,b   Masafumi Yasunami‡*b  and  Shunji Ito ORCID logo c  

* Corresponding authors

a Department of Material Science, Graduate School of Science and Technology, Shinshu University, Matsumoto 390-8621, Nagano, Japan
E-mail: tshoji@shinshu-u.ac.jp

b Department of Chemical Biology and Applied Chemistry, College of Engineering, Nihon University, Koriyama 963-8642, Fukushima, Japan

c Graduate School of Science and Technology, Hirosaki University, Hirosaki 036-8561, Aomori, Japan

Abstract

We developed a procedure for the direct synthesis of 2-arylazulenes, which were obtained in moderate to excellent yields, by [8+2] cycloaddition of 2H-cyclohepta[b]furan-2-ones with aryl-substituted silyl enol ethers. The structures of some 2-arylazulenes were clarified by single-crystal X-ray analysis. The 2-phenylazulene derivatives obtained by this study showed noticeable fluorescence in acidic media.

Graphical abstract: Direct synthesis of 2-arylazulenes by [8+2] cycloaddition of 2H-cyclohepta[b]furan-2-ones with silyl enol ethers

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Article information

DOI
https://doi.org/10.1039/C9CC09376A
Article type
Communication
Submitted
03 Dec 2019
Accepted
20 Dec 2019
First published
20 Dec 2019

Chem. Commun., 2020,56, 1485-1488

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Direct synthesis of 2-arylazulenes by [8+2] cycloaddition of 2H-cyclohepta[b]furan-2-ones with silyl enol ethers

T. Shoji, S. Sugiyama, Y. Kobayashi, A. Yamazaki, Y. Ariga, R. Katoh, H. Wakui, M. Yasunami and S. Ito, Chem. Commun., 2020, 56, 1485 DOI: 10.1039/C9CC09376A

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