Reactions of some ortho and para halogenated aromatic nitriles with ethylenediamine: selective synthesis of imidazolines

The reaction of ethylenediamine (EDA) with ortho and/or para halogenated benzonitriles did not lead to the imidazolines expected: a competitive aromatic nucleophilic substitution (S NAr) was observed instead. The selective synthesis of these imidazolines was performed by nucleophilic addition of EDA...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 60; no. 25; pp. 5325 - 5330
Main Authors Crane, Louis J., Anastassiadou, Maria, Stigliani, Jean-Luc, Baziard-Mouysset, Geneviève, Payard, Marc
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.06.2004
Elsevier
Subjects
Aromatic nucleophilic substitution
Benzonitriles
Chemistry
Chemistry, Organic
Nucleophilic addition
Phenylimidazolines
Physical Sciences
Science & Technology
Thiobenzamides
Benzonitriles
Phenylimidazolines
Thiobenzamides
Aromatic nucleophilic substitution
Nucleophilic addition
OXIDATION
ALPHA-2-ADRENOCEPTORS
benzonitriles
ANALOGS
INSULIN-SECRETION
BIOLOGICAL-ACTIVITIES
aromatic nucleophilic substitution
RAT MODEL
phenylimidazolines
thiobenzamides
GLUCOSE-HOMEOSTASIS
LIGANDS
ANTAGONISTS
nucleophilic addition
DERIVATIVES
Online AccessGet full text

Cover

More Information
Summary:The reaction of ethylenediamine (EDA) with ortho and/or para halogenated benzonitriles did not lead to the imidazolines expected: a competitive aromatic nucleophilic substitution (S NAr) was observed instead. The selective synthesis of these imidazolines was performed by nucleophilic addition of EDA to thiobenzamide derivatives. The difference in reactivity between the nitrile and thioamide derivatives was estimated by a frontier orbital approach at the RHF/6-31G** level which predicted a greater reactivity of substituted thiobenzamides towards the nucleophilic addition of EDA. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.04.075