Efficient Synthesis of Chromenes from Vinyl o-Quinone Methides via a Brønsted Acid Catalyzed Electrocyclization Process

Si-Jia Liu; Xiao-Li Jiang; Shu-Fang Wu; Man-Su Tu; Guang-Jian Mei; Feng Shi

doi:10.1055/s-0037-1609483

Synthesis, Table of Contents

Synthesis 2018; 50(12): 2416-2422
DOI: 10.1055/s-0037-1609483

paper

Efficient Synthesis of Chromenes from Vinyl o-Quinone Methides via a Brønsted Acid Catalyzed Electrocyclization Process

Si-Jia Liu

,

Xiao-Li Jiang

,

Shu-Fang Wu

School of Chemistry and Materials Science, and the Key Laboratory of Biotechnology for Medicinal Plants of Jiangsu Province, Jiangsu Normal University, Xuzhou, 221116, P. R. of China Email: fshi@jsnu.edu.cn Email: guangjianM@jsnu.edu.cn Email: mstu2016@126.com

,

Man-Su Tu*

School of Chemistry and Materials Science, and the Key Laboratory of Biotechnology for Medicinal Plants of Jiangsu Province, Jiangsu Normal University, Xuzhou, 221116, P. R. of China Email: fshi@jsnu.edu.cn Email: guangjianM@jsnu.edu.cn Email: mstu2016@126.com

,

Guang-Jian Mei*

School of Chemistry and Materials Science, and the Key Laboratory of Biotechnology for Medicinal Plants of Jiangsu Province, Jiangsu Normal University, Xuzhou, 221116, P. R. of China Email: fshi@jsnu.edu.cn Email: guangjianM@jsnu.edu.cn Email: mstu2016@126.com

,

Feng Shi *

School of Chemistry and Materials Science, and the Key Laboratory of Biotechnology for Medicinal Plants of Jiangsu Province, Jiangsu Normal University, Xuzhou, 221116, P. R. of China Email: fshi@jsnu.edu.cn Email: guangjianM@jsnu.edu.cn Email: mstu2016@126.com

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Abstract

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Abstract

An efficient approach for the synthesis of chromene derivatives from vinyl o-quinone methides was established via a Brønsted acid catalyzed electrocyclization. By using this methodology, a series of structurally diversified chromenes was synthesized in a highly atom-economic and environmentally benign manner with generally good to excellent yields (up to 98% yield). This reaction will not only provide an efficient method for the construction of chromene scaffolds, but also enrich the research area of o-quinone methides.

Key words

o-quinone methide - electrocyclization - Brønsted acid catalysis - chromenes - heterocycles

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References

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