[1,2,3]Triazolo[1,5-a]pyridines. A theoretical (DFT) study of the ring-chain isomerization

被引：18

作者：

Blanco, Fernando ^{[1
]}

Alkorta, Ibon ^{[1
]}

Elguero, Jose ^{[1
]}

Cruz, Victor ^{[2
]}

Abarca, Belen ^{[3
]}

Ballesteros, Rafael ^{[3
]}

机构：

[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain

[2] CSIC, Inst Estructura Mat, E-28006 Madrid, Spain

[3] Univ Valencia, Fac Farm, Dept Quim Organ, E-46100 Valencia, Spain

来源：

TETRAHEDRON | 2008年 / 64卷 / 49期

关键词：

Triazolopyridine; Isomerization; Substituent effects; Protonation; Deprotonation; Lithiation;

D O I：

10.1016/j.tet.2008.09.064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ring opening isomerization of [1,2,3]triazolo[1,5-a]pyridines to the corresponding 2-pyridyl derivatives has been studied by means of DFT calculations at the B3LYP/6-31+G(d,p) computational level. The effect of the substitution as well as those of protonation, deprotonation, and lithiation on different positions has been studied. The electronic characteristics of the optimized structures have been analyzed by means of the Atoms in Molecules (AIM), Electron Localization Function (ELF), Molecular Electrostatic Potential (MEP), and Natural Bond Orbital (NBO) methodologies. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：11150 / 11158

页数：9

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[11] CALCULATION OF THE AVERAGE PROPERTIES OF ATOMS IN MOLECULES .2. [J].