Synthesis of [1,2,3]triazolo[1,5-a]quinoxalin-4(5H)-ones through copper-catalyzed tandem reactions of N-(2-haloaryl)propiolamides with sodium azide

Jiajie Yan; Fengtao Zhou; Dongguang Qin; Tong Cai; Ke Ding; Qian Cai

doi:10.1021/ol300114w

Synthesis of [1,2,3]triazolo[1,5-a]quinoxalin-4(5H)-ones through copper-catalyzed tandem reactions of N-(2-haloaryl)propiolamides with sodium azide

Org Lett. 2012 Mar 2;14(5):1262-5. doi: 10.1021/ol300114w. Epub 2012 Feb 15.

Authors

Jiajie Yan¹, Fengtao Zhou, Dongguang Qin, Tong Cai, Ke Ding, Qian Cai

Affiliation

¹ Key Laboratory of Regenerative Biology and Institute of Chemical Biology, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou, 510530, China.

PMID: 22335274
DOI: 10.1021/ol300114w

Abstract

A simple and efficient approach for the synthesis of [1,2,3]triazolo[1,5-a]quinoxalin-4(5H)-ones is described. The methodology is based on a tandem reaction of 1-(2-haloaryl)propiolamides with sodium azide through a [3 + 2] azide-alkyne cycloaddition and intramolecular Ullmann-type C-N coupling process.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemistry*
Catalysis
Copper / chemistry*
Cyclization
Molecular Structure
Quinoxalines / chemistry*
Sodium Azide / chemistry*
Triazoles / chemical synthesis*

Substances

Amides
Quinoxalines
Triazoles
Copper
Sodium Azide