Synthesis 2017; 49(18): 4283-4291
DOI: 10.1055/s-0036-1588462
special topic
© Georg Thieme Verlag Stuttgart · New York

tert-Butyl Hypochlorite Induced Cyclization of Ethyl 2-(N-Aryl­carbamoyl)-2-iminoacetates

Dianjun Li
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China   Email: liying@lzu.edu.cn   Email: yuwei@lzu.edu.cn
,
Ying Li*
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China   Email: liying@lzu.edu.cn   Email: yuwei@lzu.edu.cn
,
Wei Yu*
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China   Email: liying@lzu.edu.cn   Email: yuwei@lzu.edu.cn
› Author Affiliations
The authors thank the National Natural Science Foundation of China (No. 21372108) for financial support
Further Information

Publication History

Received: 12 April 2017

Accepted after revision: 22 May 2017

Publication Date:
03 July 2017 (online)

Published as part of the Special Topic Modern Cyclization Strategies in Synthesis

Abstract

Ethyl 2-(N-arylcarbamoyl)-2-iminoacetates can be transformed into the corresponding quinoxalin-2-ones in high yield by using the oxidation system of tert-butyl hypochlorite, tetrabutylammonium iodide and tetrabutylammonium chloride. Oxygen exhibits a beneficial effect on the reaction. The reaction is proposed to follow an iminyl radical cyclization mechanism where azaspirocyclohexadienylperoxyl radical is formed as a key intermediate. The quinoxalin-2-one is derived from the azaspirocyclohexadienylperoxyl radical via concurrent oxygen extrusion and rearrangement.

Supporting Information

 
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