The influence of substitution in the quinoxaline nucleus on 1,3-dipolar cycloaddition reactions: A DFT study

被引：7
作者：
Lauria, Antonino [1 ]
Almerico, Anna Maria [1 ]
Barone, Giampaolo [1 ,2 ]
机构：
[1] Univ Palermo, Dipartimento Sci & Tecnol Biol Chim & Farmaceut, I-90128 Palermo, Italy
[2] Ist EuroMediterraneo Sci & Tecnol, I-90139 Palermo, Italy
来源：
COMPUTATIONAL AND THEORETICAL CHEMISTRY | 2013年 / 1013卷
关键词：
DFT calculations; 1,3-Dipolar cycloaddition reactions; Quinoxalines; Reaction mechanism; BIOLOGICAL INTEREST; RING-SYSTEM; DOMINO REACTION; DENSITY; REARRANGEMENT; DERIVATIVES; REACTIVITY; ENERGIES; PYRROLO; MODEL;
D O I：
10.1016/j.comptc.2013.03.017
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The reaction mechanism of 1,3-dipolar cycloadditions of both symmetric and unsymmetric benzo-condensed diazines with a nitrilimine dipole, to give two different mono- and bis-cycloadducts, in tetrahydrofuran (THF) solution, was studied by DFT calculations. The results obtained show that each 1,3-dipolar cycloaddition reaction always proceeds by a two steps mechanism, in which the first intermediate shows only one covalent bond between the beta carbon of the nitrilimine and the aromatic nitrogen of the diazine molecule. The structure and energy content of the two transition states of the two cycloaddition steps, in the case of the unsymmetric benzo-condensed diazine, nicely explains why the product of the bis-cycloadditions is exclusively observed and why the product of a mono-cycloaddition is not isolated for the symmetric reaction pathway. (C) 2013 Elsevier B.V. All rights reserved.
引用
收藏
页码：116 / 122
页数：7
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