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

被引：33

作者：

Chevallier, Floris ^{[1
]}

Blin, Thomas ^{[1
]}

Nagaradja, Elisabeth ^{[1
]}

Lassagne, Frederic ^{[1
]}

Roisnel, Thierry ^{[1
]}

Halauko, Yury S. ^{[2
]}

Matulis, Vadim E. ^{[3
]}

Ivashkevich, Oleg A. ^{[3
]}

Mongin, Florence ^{[1
]}

机构：

[1] Univ Rennes 1, UMR CNRS 6226, Inst Sci Chim Rennes, F-35042 Rennes, France

[2] Belarusian State Univ, Dept Electrochem, Minsk 220030, BELARUS

[3] Belarusian State Univ, Res Inst Physicochem Problems, Minsk 220030, BELARUS

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 25期

关键词：

MIXED LITHIUM-CADMIUM; DIRECTED LITHIATION; MEDIATED ZINCATION; ZINC; CHEMISTRY; AMIDE; BASE; ATE; DERIVATIVES; TRIAZOLES;

D O I：

10.1039/c2ob25554e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4878 / 4885

页数：8

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