BPO-promoted [4 + 2] cyclization of enaminones and o-phenylenediamines to 2-acyl quinoxalines via a cascade transamination and C–H amination

Heng Feng; Jie Huo; Xiaonan Mu; Renhua Zheng; Xiao Geng; Lei Wang

doi:10.1039/D4OB00494A

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BPO-promoted [4 + 2] cyclization of enaminones and o-phenylenediamines to 2-acyl quinoxalines via a cascade transamination and C–H amination†

Heng Feng,‡^ab Jie Huo,‡^b Xiaonan Mu,^ab Renhua Zheng,

*^b Xiao Geng

*^b and Lei Wang

^bc

Author affiliations

* Corresponding authors

^a Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, P. R. China

^b Department of Chemistry, Taizhou University, Jiaojiang, Zhejiang 318000, P. R. China
E-mail: zhengrh@tzc.edu.cn, xiaogeng_@tzc.edu.cn

^c College of Material Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, Zhejiang, P. R. China

Abstract

Rapid assembly of quinoxalines in a single step from readily available precursors has been recognized as an ideal platform in terms of efficiency and operation. Herein, we report a BPO-promoted metal-free approach to 2-acyl quinoxalines from enaminones and o-phenylenediamines via cascade transamination and C–H amination. This methodology demonstrates excellent compatibility with various substrates, including o-hydroxy enaminones, drug derivatives and natural products under mild reaction conditions.

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DOI: https://doi.org/10.1039/D4OB00494A
Article type: Communication
Submitted: 26 Mar 2024
Accepted: 29 Apr 2024
First published: 29 Apr 2024

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Org. Biomol. Chem., 2024,22, 4067-4071

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BPO-promoted [4 + 2] cyclization of enaminones and o-phenylenediamines to 2-acyl quinoxalines via a cascade transamination and C–H amination

H. Feng, J. Huo, X. Mu, R. Zheng, X. Geng and L. Wang, Org. Biomol. Chem., 2024, 22, 4067 DOI: 10.1039/D4OB00494A

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Organic & Biomolecular Chemistry

BPO-promoted [4 + 2] cyclization of enaminones and o-phenylenediamines to 2-acyl quinoxalines via a cascade transamination and C–H amination†

Abstract

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BPO-promoted [4 + 2] cyclization of enaminones and o-phenylenediamines to 2-acyl quinoxalines via a cascade transamination and C–H amination

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