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

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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


Submitted
03 Dec 2019
Accepted
20 Dec 2019
First published
20 Dec 2019

Chem. Commun., 2020, Advance Article
Article type
Communication

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, Advance Article , DOI: 10.1039/C9CC09376A

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