Issue 44, 2020
From the journal:

Chemical Communications

Harnessing structurally unbiased ortho-benzoquinone monoimine for biomimetic oxidative [4+2] cycloaddition with enamines†

Muhammad Adnan Bashir,a   Honghua Zuo,a   Xunbo Lu,a   Yuzhou Wu ORCID logo a  and  Fangrui Zhong ORCID logo *ab  

* Corresponding authors

a Key laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology (HUST), Wuhan 430074, China
E-mail: chemzfr@hust.edu.cn

b Shenzhen Huazhong University of Science & Technology Research Institute, Shenzhen 518000, China

Abstract

Reported herein is the first catalytic oxidative [4+2] cycloaddition of 2-aminophenols with cyclic enamines. This biomimetic catalytic oxidative strategy expediently accommodates the very labile structurally unbiased ortho-quinone monoimine intermediate for cycloaddition by controlling its formation rate, thus refraining from otherwise prerequisite steric or electronic stabilization and allowing efficient assembly of various tricyclic 1,4-benzoxazines in a step and atom economic fashion.

Graphical abstract: Harnessing structurally unbiased ortho-benzoquinone monoimine for biomimetic oxidative [4+2] cycloaddition with enamines

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Article information

DOI
https://doi.org/10.1039/D0CC01813A
Article type
Communication
Submitted
09 Mar 2020
Accepted
15 Apr 2020
First published
15 Apr 2020

Chem. Commun., 2020,56, 5965-5968

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Harnessing structurally unbiased ortho-benzoquinone monoimine for biomimetic oxidative [4+2] cycloaddition with enamines

M. A. Bashir, H. Zuo, X. Lu, Y. Wu and F. Zhong, Chem. Commun., 2020, 56, 5965 DOI: 10.1039/D0CC01813A

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