Issue 25, 2012
From the journal:

Organic & Biomolecular Chemistry

Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles†

Floris Chevallier,*a   Thomas Blin,a   Elisabeth Nagaradja,a   Frédéric Lassagne,a   Thierry Roisnel,a   Yury S. Halauko,*b   Vadim E. Matulis,c   Oleg A. Ivashkevichc  and  Florence Mongin*a  

* Corresponding authors

a Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS- Université de Rennes 1, Bâtiment 10A, Case 1003, Campus Scientifique de Beaulieu, 35042 Rennes, France
E-mail: floris.chevallier@univ-rennes1.fr, florence.mongin@univ-rennes1.fr
Fax: +33-2-2323-6955

b Department of Electrochemistry of Belarusian State University, 14 Leningradskaya Str., Minsk, Belarus
E-mail: hys@tut.by, halauko@bsu.by

c Research Institute for Physico-Chemical Problems of Belarusian State University, 14 Leningradskaya Str., Minsk, Belarus
Fax: +375-17-2264696

Abstract

2-Aryl-1,2,3-triazoles were synthesized by cyclization of the corresponding glyoxal arylosazones, generated from commercial arylhydrazines. The deproto-metallation of 2-phenyl-1,2,3-triazole was attempted using different 2,2,6,6-tetramethylpiperidino-based mixed lithium–metal (Zn, Cd, Cu, Co, Fe) combinations, giving results in the case of Zn, Cd, and Cu. The lithium–zinc combination was next selected to apply the deprotonation–iodination sequence to all the 2-aryl-1,2,3-triazoles synthesized. The results were analyzed with the help of the CH acidities of the substrates, determined in THF solution using the DFT B3LYP method.

Graphical abstract: Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles

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Article information

DOI
https://doi.org/10.1039/C2OB25554E
Article type
Paper
Submitted
14 Mar 2012
Accepted
01 May 2012
First published
01 May 2012

Org. Biomol. Chem., 2012,10, 4878-4885

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Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles

F. Chevallier, T. Blin, E. Nagaradja, F. Lassagne, T. Roisnel, Y. S. Halauko, V. E. Matulis, O. A. Ivashkevich and F. Mongin, Org. Biomol. Chem., 2012, 10, 4878 DOI: 10.1039/C2OB25554E

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