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Yuan Y, Dong WH, Gao XS, et al. Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: synthesis of cyclopenta[b]quinoxalines. Chem Commun (Camb). 2019;55(79):11900-11903doi: 10.1039/c9cc05655f.
Yuan, Y., Dong, W. H., Gao, X. S., Xie, X. M., & Zhang, Z. G. (2019). Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: synthesis of cyclopenta[b]quinoxalines. Chemical communications (Cambridge, England), 55(79), 11900-11903. https://doi.org/10.1039/c9cc05655f
Yuan, Yao, et al. "Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: synthesis of cyclopenta[b]quinoxalines." Chemical communications (Cambridge, England) vol. 55,79 (2019): 11900-11903. doi: https://doi.org/10.1039/c9cc05655f
Yuan Y, Dong WH, Gao XS, Xie XM, Zhang ZG. Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: synthesis of cyclopenta[b]quinoxalines. Chem Commun (Camb). 2019 Oct 01;55(79):11900-11903. doi: 10.1039/c9cc05655f. PMID: 31528936.
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Chem Commun (Camb). 2019 Oct 01;55(79):11900-11903. doi: 10.1039/c9cc05655f.

Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: synthesis of cyclopenta[b]quinoxalines.

Chemical communications (Cambridge, England)

Yao Yuan, Wu-Heng Dong, Xiao-Shuang Gao, Xiao-Min Xie, Zhao-Guo Zhang

Affiliations

  1. Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China. [email protected].
  2. College of Medicine, Guangxi University of Science and Technology, Liuzhou, Guangxi 545006, China.
  3. Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China. [email protected] and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Fenglin Road, Shanghai 200032, China.

PMID: 31528936 DOI: 10.1039/c9cc05655f

Abstract

A visible-light-induced radical cascade cyclization of aryl isonitriles and cyclobutanone oxime esters for the synthesis of cyclopenta[b]quinoxalines has been accomplished for the first time. The key to the success of this process was the integration of the in situ-formed nitrile radical followed by the cascade radical isonitrile/nitrile insertion-cyclization. The easy introduction of substituents for both substrates and the high functional group tolerance of the reaction make it an efficient strategy to give various quinoxaline derivatives in moderate to good yields.

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