A DFT study for the formation of imidazo[1,2-c]pyrimidines through an intramolecular Michael addition

被引：8
作者：
Domingo, Luis R.
Saez, Jose A.
Palmucci, Cristina
Sepulveda-Arques, Jose
Gonzalez-Rosende, M. Eugenia
机构：
[1] Univ Valencia, Dept Quim Organ, ICMOL, E-46100 Burjassot, Valencia, Spain
[2] Univ Cardenal Herrera, Dept Quim, Moncada 46113, Valencia, Spain
来源：
TETRAHEDRON | 2006年 / 62卷 / 44期
关键词：
pyrimidines; cyclization; Michael addition; electrophilicity; DFT calculations;
D O I：
10.1016/j.tet.2006.08.066
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The formation of imidazo[1,2-c]pyrimidines through a ring closure of 2-(2-sulfonylimino-1,2-dihydro-1-pyrimidinyl) acetamides has been studied using DFT methods. Analysis of the energy results for the cyclization step shows the demand of almost an acid catalyst, which increases the electrophilicity of the dihydropyrimidine moiety, in order to make feasible the intramolecular Michael addition. The substitution on both dihydropyrimidine and amide moieties has also an influence on the cyclization step. (c) 2006 Elsevier Ltd. All rights reserved.
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页码：10408 / 10416
页数：9
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