Issue 2, 2013
From the journal:

Organic & Biomolecular Chemistry

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

Su-Xia Xu,a   Lu Hao,a   Tao Wang,a   Zong-Cang Dinga  and  Zhuang-Ping Zhan*a  

* Corresponding authors

a Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. China
E-mail: zpzhan@xmu.edu.cn
Fax: +86 (0)592 2180318
Tel: +86 (0)592-2180318

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.

Graphical abstract: Chemoselective synthesis of substituted pyrazoles through AgOTf-catalyzed cascade propargylic substitution–cyclization–aromatization

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Article information

DOI
https://doi.org/10.1039/C2OB27016A
Article type
Paper
Submitted
04 Sep 2012
Accepted
06 Nov 2012
First published
06 Nov 2012

Org. Biomol. Chem., 2013,11, 294-298

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

S. Xu, L. Hao, T. Wang, Z. Ding and Z. Zhan, Org. Biomol. Chem., 2013, 11, 294 DOI: 10.1039/C2OB27016A

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