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

Chem Commun (Camb)

Department of Material Science, Graduate School of Science and Technology, Shinshu University, Matsumoto 390-8621, Nagano, Japan.

Published: February 2020

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.

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http://dx.doi.org/10.1039/c9cc09376aDOI Listing

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