Silver-Catalyzed Dearomative [3+2] Spiroannulation of Aryl Oxamic Acids with Alkynes

Cheng-An Jin; Ren-Xiao Liang; Yi-Xia Jia

doi:10.1055/a-2359-8967

Synthesis, Table of Contents

Synthesis 2024; 56(20): 3191-3198
DOI: 10.1055/a-2359-8967

paper

Silver-Catalyzed Dearomative [3+2] Spiroannulation of Aryl Oxamic Acids with Alkynes

Authors

Cheng-An Jin

^aCollege of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou 310014, P. R. of China

^bCollege of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing 312000, P. R. of China
Ren-Xiao Liang∗

^aCollege of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou 310014, P. R. of China
Yi-Xia Jia

^aCollege of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou 310014, P. R. of China

^cState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

Abstract

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Abstract

A silver-catalyzed dearomative decarboxylative [3+2] spiroannulation of aryl oxamic acids with alkynes is described. The reaction provides reliable access to a range of azaspiro[4,5]trienones in moderate yields in aqueous media. In addition, the reaction exhibits a broad substrate scope and good functional group compatibility.

Key words

silver-catalyzed - dearomative - [3+2] spiroannulation - oxamic acid - alkyne - azaspiro[4,5]trienone

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