Organocatalytic [4 + 2] cyclizations of para-quinone methide derivatives with isocyanates

Yu-Chun Cheng; Cong-Shuai Wang; Tian-Zhen Li; Feng Gao; Yinchun Jiao; Feng Shi

doi:10.1039/C9OB00918C

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Organocatalytic [4 + 2] cyclizations of para-quinone methide derivatives with isocyanates†

Yu-Chun Cheng,‡^a Cong-Shuai Wang,‡^a Tian-Zhen Li,^a Feng Gao,

*^a Yinchun Jiao*^b and Feng Shi

*^a

Author affiliations

* Corresponding authors

^a School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, China
E-mail: fshi@jsnu.edu.cn, gf2016@jsnu.edu.cn

^b School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, P. R. China
E-mail: yinchunjiao@hnust.edu.cn

Abstract

The first [4 + 2] cyclizations of para-quinone methide derivatives with isocyanates have been established under the catalysis of Brønsted acids or Brønsted bases, which efficiently constructed benzoxazin-2-one frameworks in generally high yields (up to 95%). This reaction will not only enrich the research contents of para-quinone methide-involved cyclization reactions but also provide a useful method for constructing biologically important benzoxazin-2-one frameworks.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/C9OB00918C
Article type: Paper
Submitted: 22 Apr 2019
Accepted: 17 Jun 2019
First published: 17 Jun 2019

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Org. Biomol. Chem., 2019,17, 6662-6670

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Organocatalytic [4 + 2] cyclizations of para-quinone methide derivatives with isocyanates

Y. Cheng, C. Wang, T. Li, F. Gao, Y. Jiao and F. Shi, Org. Biomol. Chem., 2019, 17, 6662 DOI: 10.1039/C9OB00918C

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Organic & Biomolecular Chemistry

Organocatalytic [4 + 2] cyclizations of para-quinone methide derivatives with isocyanates†

Abstract

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Organocatalytic [4 + 2] cyclizations of para-quinone methide derivatives with isocyanates

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