Study of the nucleophilic behaviour of N-phenylbenzamidine towards 1,2-diaza-1,3-dienes: domino reactions for imidazole scaffolds

被引：10

作者：

Attanasi, Orazio A. ^{[1
]}

Bartoccini, Silvia ^{[1
]}

Giorgi, Gianluca ^{[2
]}

Mantellini, Fabio ^{[1
]}

Perrulli, Francesca R. ^{[1
]}

Santeusanio, Stefania ^{[1
]}

机构：

[1] Univ Urbino Carlo Bo, Inst Organ Chem, I-61029 Urbino, Italy

[2] Univ Siena, Dept Chem, I-53100 Siena, Italy

来源：

TETRAHEDRON | 2010年 / 66卷 / 27-28期

关键词：

1,2-Diaza-1,3-dienes; Tautomerism; Michael addition; Nitrogen heterocycles; Spiro compounds; CATALYZED SYNTHESIS;

D O I：

10.1016/j.tet.2010.04.108

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Depending on the nature of the solvent, alcohol or DMF, N-phenylbenzamidine shows different nucleophilic behaviour towards the conjugated azo-ene system of 1,2-diaza-1,3-dienes. In alcohol it reacts as a nucleophile through the N-phenyl imino nitrogen affording spiro pyrroloimidazoles and 1,3-diphenyl-1H-imidazoles. In DMF, by contrast, it behaves as nucleophile mainly by means of the imino amidino nitrogen providing 2-phenylimidazole derivatives by loss of the aniline molecule. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：5121 / 5129

页数：9

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