Oxidative cascade cyclization of N-arylacrylamides with TMSN3

Bo Jiang; Tai-Gang Fan; Yu-Song Ran; Yun-Tao Shen; Cui Zhang; Wei Jiang; Ya-Min Li

doi:10.1039/D3OB01951A

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Oxidative cascade cyclization of N-arylacrylamides with TMSN₃†

Bo Jiang,^a Tai-Gang Fan,^a Yu-Song Ran,^a Yun-Tao Shen,^a Cui Zhang,^a Wei Jiang^a and Ya-Min Li

*^a

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* Corresponding authors

^a Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P. R. China
E-mail: liym@kust.edu.cn

Abstract

An azido-radical-triggered cyclization of N-(o-cyanobiaryl)acrylamides with TMSN₃via a C(sp³)–N/C(sp²)–C(sp³)/C(sp²)–N bond formation cascade is described. This reaction features mild conditions and high bond-forming efficiency, making it an efficient method for the construction of azide-substituted pyridophenanthridines.

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Article information

DOI: https://doi.org/10.1039/D3OB01951A
Article type: Paper
Submitted: 01 Dec 2023
Accepted: 01 Jan 2024
First published: 03 Jan 2024

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Org. Biomol. Chem., 2024,22, 1186-1193

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Oxidative cascade cyclization of N-arylacrylamides with TMSN₃

B. Jiang, T. Fan, Y. Ran, Y. Shen, C. Zhang, W. Jiang and Y. Li, Org. Biomol. Chem., 2024, 22, 1186 DOI: 10.1039/D3OB01951A

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Organic & Biomolecular Chemistry