Copper-catalyzed oxidative cyclization of 2-(1H-pyrrol-1-yl)aniline and alkylsilyl peroxides: a route to pyrrolo[1,2-a]quinoxalines

Zhenyu An; Man Miao; Fengkai Sun; Xiao-Bing Lan; Jian-Qiang Yu; Xiaoli Guo; Jian Zhang

doi:10.1039/D3OB01934A

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Copper-catalyzed oxidative cyclization of 2-(1H-pyrrol-1-yl)aniline and alkylsilyl peroxides: a route to pyrrolo[1,2-a]quinoxalines†

Zhenyu An,

‡^a Man Miao,‡^a Fengkai Sun,^a Xiao-Bing Lan,^a Jian-Qiang Yu,

^a Xiaoli Guo*^a and Jian Zhang

*^ab

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* Corresponding authors

^a College of Pharmacy, Key Laboratory of Protection, Development and Utilization of Medicinal Resources in Liupanshan Area, Ministry of Education, Ningxia Medical University, Yinchuan, Ningxia Hui Autonomous Region, China
E-mail: jian.zhang@sjtu.edu.cn, gxl2018666@163.com

^b Medicinal Chemistry and Bioinformatics Center, Shanghai Jiao Tong University School of Medicine, Shanghai, China

Abstract

An efficient method was developed for the one-pot construction of pyrrolo[1,2-a]quinoxalines via a Cu(II)-catalyzed domino reaction between 2-(1H-pyrrol-1-yl)anilines and alkylsilyl peroxides. This reaction proceeds through C–C bond cleavage and new C–C and C–N bond formation. A mechanistic study suggests that alkyl radical species participate in the cascade reaction.

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DOI: https://doi.org/10.1039/D3OB01934A
Article type: Communication
Submitted: 28 Nov 2023
Accepted: 22 Feb 2024
First published: 24 Feb 2024

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Org. Biomol. Chem., 2024,22, 2370-2374

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Copper-catalyzed oxidative cyclization of 2-(1H-pyrrol-1-yl)aniline and alkylsilyl peroxides: a route to pyrrolo[1,2-a]quinoxalines

Z. An, M. Miao, F. Sun, X. Lan, J. Yu, X. Guo and J. Zhang, Org. Biomol. Chem., 2024, 22, 2370 DOI: 10.1039/D3OB01934A

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Organic & Biomolecular Chemistry

Copper-catalyzed oxidative cyclization of 2-(1H-pyrrol-1-yl)aniline and alkylsilyl peroxides: a route to pyrrolo[1,2-a]quinoxalines†

Abstract

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Copper-catalyzed oxidative cyclization of 2-(1H-pyrrol-1-yl)aniline and alkylsilyl peroxides: a route to pyrrolo[1,2-a]quinoxalines

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