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Synthesis 2012; 44(10): 1577-1583
DOI: 10.1055/s-0031-1290772
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© Georg Thieme Verlag Stuttgart · New York

An Efficient One-Pot Synthesis of 3,5-Disubstituted 1H-Pyrazoles

Lei-Lei Wu
a   Key Lab of Green Chemistry and Technology, Ministry of Education, The Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. of China, Fax: +86(28)85412904   Email: scuhchen@scu.edu.cn
,
Yi-Cen Ge
a   Key Lab of Green Chemistry and Technology, Ministry of Education, The Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. of China, Fax: +86(28)85412904   Email: scuhchen@scu.edu.cn
,
Ting He
b   Institute of Chemical Materials, China Academy of Engineering Physics (CAEP), Chengdu, Sichuan 610065, P. R. of China
,
Lei Zhang
a   Key Lab of Green Chemistry and Technology, Ministry of Education, The Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. of China, Fax: +86(28)85412904   Email: scuhchen@scu.edu.cn
,
Xing-Li Fu
c   Guangxi Vocational and Technical Institute of Industry, Nanning, Guangxi 530001, P. R. of China
,
Hai-Yan Fu
a   Key Lab of Green Chemistry and Technology, Ministry of Education, The Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. of China, Fax: +86(28)85412904   Email: scuhchen@scu.edu.cn
,
Hua Chen*
a   Key Lab of Green Chemistry and Technology, Ministry of Education, The Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. of China, Fax: +86(28)85412904   Email: scuhchen@scu.edu.cn
,
Rui-Xiang Li
a   Key Lab of Green Chemistry and Technology, Ministry of Education, The Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. of China, Fax: +86(28)85412904   Email: scuhchen@scu.edu.cn
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Publication History

Received: 01 December 2011

Accepted after revision: 29 February 2012

Publication Date:
19 April 2012 (online)

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Abstract

An efficient, general, one-pot, three-component procedure for the preparation of 3,5-disubstituted 1H-pyrazoles via condensation of substituted aromatic aldehydes, tosylhydrazine and terminal alkynes in toluene is reported. The reaction tolerates a variety of functional groups and sterically hindered substrates to afford the desired pyrazoles in yields of 67–91%.

Key words

pyrazoles - heterocycles - condensation - cycloaddition - aldehydes

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