Synlett 2018; 29(17): 2283-2287
DOI: 10.1055/s-0037-1610271
letter
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Synthesis of Substituted 4-Acylpyrazole Derivatives through a Cascade Transformation from N-Propargylic Sulfonylhydrazones and Diaryliodonium Salts

Ren-Hao Li
a   Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, P. R. of China   eMail: yhchen@xmu.edu.cn
,
Xin-Yang Fan
a   Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, P. R. of China   eMail: yhchen@xmu.edu.cn
,
Zi-Lin Hu
a   Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, P. R. of China   eMail: yhchen@xmu.edu.cn
,
Zhi-Kai Liu
a   Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, P. R. of China   eMail: yhchen@xmu.edu.cn
,
Ying Yang
a   Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, P. R. of China   eMail: yhchen@xmu.edu.cn
,
Hai-Tao Tang
b   State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, P. R. of China
,
Yi-Hui Chen*
a   Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, P. R. of China   eMail: yhchen@xmu.edu.cn
,
Li Chen
a   Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, P. R. of China   eMail: yhchen@xmu.edu.cn
,
Zhuang-Ping Zhan
a   Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, P. R. of China   eMail: yhchen@xmu.edu.cn
› Institutsangaben
Financial support from the National Natural Science Foundation of China (no. 21772166) and the NFFTBS (no. J1310024) is gratefully acknowledged.
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Publikationsverlauf

Received: 02. Juli 2018

Accepted after revision: 14. August 2018

Publikationsdatum:
03. September 2018 (online)


Abstract

A concise strategy for the synthesis of substituted 4-acylpyrazole derivatives from N-propargylic sulfonylhydrazones and diaryliodonium salts has been developed. The pyrazole derivatives are formed through a five-step cascade sequence that includes intramolecular cyclization, hydroxylation, elimination, copper-catalyzed aerobic oxidation, and intramolecular rearrangement.

Supporting Information