Synthesis 2023; 55(17): 2683-2690
DOI: 10.1055/a-2067-4099
paper

Cu(OTf)2/TBHP/O2-Mediated Tandem Oxidative Reaction: Easy Access to Benzopyrano[4,3-b]pyridines

Dongping Cheng
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Hongjiao Yang
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Hongshuang Xia
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Huafang Gu
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Jing-Hua Li
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Xiaoliang Xu
b   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
› Author Affiliations
This work was supported by the National Natural Science Foundation of China (22078300).


Abstract

An effective tandem reaction of 4-aminocoumarins and 1,3-diarylpropenes mediated by Cu(OTf)2/TBHP (tert-butyl hydroperoxide)/O2 that provides various benzopyrano[4,3-b]pyridines in moderate to good yields is disclosed. The reaction proceeds through oxidative coupling, intramolecular cyclization, and dehydro-aromatization. This approach has the advantages of high atom-economy, environmental compatibility, and wide substrate scope.

Supporting Information



Publication History

Received: 07 February 2023

Accepted after revision: 31 March 2023

Accepted Manuscript online:
31 March 2023

Article published online:
08 May 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany