Issue 56, 2012
From the journal:

Chemical Communications

Intramolecular hydrogen bonding-assisted cyclocondensation of α-diazoketones with various amines: a strategy for highly efficient Wolff 1,2,3-triazole synthesis†

Zikun Wang,a   Xihe Bi,*bc   Peiqiu Liao,b   Rui Zhang,a   Yongjiu Lianga  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, Tianjin 300071, China

Abstract

A catalytic and highly efficient Wolff's cyclocondensation of α-diazoketones with aromatic and aliphatic amines has been realized for the first time by utilizing the strategy of an intramolecular hydrogen bonding-activating carbonyl group. This approach successfully solved the challenging problem of poor condensation efficiency in Wolff 1,2,3-triazole synthesis, and constitutes a powerful method for the synthesis of highly functionalized 1,2,3-triazoles.

Graphical abstract: Intramolecular hydrogen bonding-assisted cyclocondensation of α-diazoketones with various amines: a strategy for highly efficient Wolff 1,2,3-triazole synthesis

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Article information

DOI
https://doi.org/10.1039/C2CC33157H
Article type
Communication
Submitted
02 May 2012
Accepted
23 May 2012
First published
24 May 2012

Chem. Commun., 2012,48, 7076-7078

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Intramolecular hydrogen bonding-assisted cyclocondensation of α-diazoketones with various amines: a strategy for highly efficient Wolff 1,2,3-triazole synthesis

Z. Wang, X. Bi, P. Liao, R. Zhang, Y. Liang and D. Dong, Chem. Commun., 2012, 48, 7076 DOI: 10.1039/C2CC33157H

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