Issue 2, 2013
From the journal:

RSC Advances

Solvent-controlled, regio-switchable formation of 3-/5-arylaminopyrazole isomer in cyclocondensation of β-aminoenones with hydrazides: intermolecular hydrogen bonding plays a role†

Dexuan Xiang,a   Xihe Bi,*bc   Peiqiu Liao,b   Guichun Fang,b   Zikun Wang,b   Xiaoqing Xina  and  Dewen Dong*ab  

* Corresponding authors

a Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, China
E-mail: dwdong@ciac.jl.cn

b Department of Chemistry, Northeast Normal University, Changchun, China
E-mail: bixh507@nenu.edu.cn

c State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

Abstract

An unprecedented solvent-controlled, regio-switchable Knorr-type reaction for the synthesis of pyrazoles has been realized in the cyclocondensation of β-aminoenones with hydrazides. Single regioisomer of 3- or 5-arylaminopyrazole can be obtained simply by changing the reaction solvent. Using hydrazine hydrate, only 3-arylaminopyrazoles were produced.

Graphical abstract: Solvent-controlled, regio-switchable formation of 3-/5-arylaminopyrazole isomer in cyclocondensation of β-aminoenones with hydrazides: intermolecular hydrogen bonding plays a role

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Article information

DOI
https://doi.org/10.1039/C2RA22647B
Article type
Communication
Submitted
25 Oct 2012
Accepted
13 Nov 2012
First published
26 Nov 2012

RSC Adv., 2013,3, 386-389

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Solvent-controlled, regio-switchable formation of 3-/5-arylaminopyrazole isomer in cyclocondensation of β-aminoenones with hydrazides: intermolecular hydrogen bonding plays a role

D. Xiang, X. Bi, P. Liao, G. Fang, Z. Wang, X. Xin and D. Dong, RSC Adv., 2013, 3, 386 DOI: 10.1039/C2RA22647B

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