Organic & Biomolecular Chemistry 2013-01-14

Chemoselective synthesis of substituted pyrazoles through AgOTf-catalyzed cascade propargylic substitution-cyclization-aromatization.

Su-Xia Xu, Lu Hao, Tao Wang, Zong-Cang Ding, Zhuang-Ping Zhan

Index: Org. Biomol. Chem. 11(2) , 294-8, (2013)

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Abstract

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.