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Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. China
E-mail: zpzhan@xmu.edu.cn
; Fax: +86 (0)592 2180318
; Tel: +86 (0)592-2180318
Org. Biomol. Chem., 2013,11, 294-298
DOI:
10.1039/C2OB27016A
Received
04 Sep 2012,
Accepted
06 Nov 2012
First published online
06 Nov 2012
A cascade AgOTf-catalyzed chemoselective approach to 3,5/1,3-disubstitued pyrazoles from propargylic alcohols and para-tolylsulfonohydrazide has been developed. Good chemoselectivity is observed depending on the different substituents in the alkyne moiety of the propargylic alcohols, generating two different kinds of products through different aromatization mechanisms. The pyrazolo[5,1-a]isoquinoline skeleton can also be effectively constructed by this method through a cascade bicyclization process.