Synthesis 2017; 49(17): 3863-3873
DOI: 10.1055/s-0036-1590791
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© Georg Thieme Verlag Stuttgart · New York

Diversified Synthesis of 2-(4-Oxo[1,2,3]triazolo[1,5-a]quinoxalin-5(4H)-yl)acetamide Derivatives through Ugi-4-CR and Copper-Catalyzed Tandem Reactions

Yu An
a  College of Pharmacy, Jinan University, No. 601 Huangpu Avenue West, Guangzhou, 510632, P. R. of China   Email: luxy2016@jnu.edu.cn   Email: caiqian@jnu.edu.cn
b  College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, P. R. of China
,
Huan He
a  College of Pharmacy, Jinan University, No. 601 Huangpu Avenue West, Guangzhou, 510632, P. R. of China   Email: luxy2016@jnu.edu.cn   Email: caiqian@jnu.edu.cn
b  College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, P. R. of China
,
Tiantian Liu
a  College of Pharmacy, Jinan University, No. 601 Huangpu Avenue West, Guangzhou, 510632, P. R. of China   Email: luxy2016@jnu.edu.cn   Email: caiqian@jnu.edu.cn
b  College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, P. R. of China
,
Yong Zhang
b  College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, P. R. of China
,
Xiaoyun Lu*
a  College of Pharmacy, Jinan University, No. 601 Huangpu Avenue West, Guangzhou, 510632, P. R. of China   Email: luxy2016@jnu.edu.cn   Email: caiqian@jnu.edu.cn
,
a  College of Pharmacy, Jinan University, No. 601 Huangpu Avenue West, Guangzhou, 510632, P. R. of China   Email: luxy2016@jnu.edu.cn   Email: caiqian@jnu.edu.cn
› Author Affiliations
The authors are grateful to National Natural Science Foundation of China (Grant 21572229) and Science and Technology Program of Guangzhou, China (Grant 201604016066) for their financial support.
Further Information

Publication History

Received: 25 April 2017

Accepted after revision: 12 May 2017

Publication Date:
11 July 2017 (online)


§ These authors contributed equally.

Abstract

A diversified synthesis of 2-(4-oxo[1,2,3]triazolo-[1,5-a]quin­oxalin-5(4H)-yl)acetamide derivatives is demonstrated. The protocol employs a Ugi four-component reaction for the assembling of N-(2-haloaryl)propynamide intermediates and followed by a copper-catalyzed tandem reaction of the synthetic N-(2-haloaryl)propynamides with sodium azide. Such a method provides rapid access to structurally varied and complex fused tricyclic scaffolds through readily available starting materials.

Supporting Information

 
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