Synthesis of Heterocycles by Intramolecular Nucleophilic Substitution at an Electron-Deficient sp2 Nitrogen Atom

被引：13

作者：

Saczewski, Jaroslaw ^{[1
]}

Gdaniec, Maria ^{[2
]}

机构：

[1] Med Univ Gdansk, Dept Chem Technol Drugs, PL-80416 Gdansk, Poland

[2] Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 12期

关键词：

Nucleophilic addition; Amination; Nucleophilic substitution; Nitrogen heterocycles; Transition states; GRIGNARD-REAGENTS; VINYLIC CARBON; PRIMARY AMINES; N BOND; AMINATION; REARRANGEMENT; CONFIGURATION; INVERSION; MECHANISM; IONS;

D O I：

10.1002/ejoc.200901520

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Aryl(arylsulfony1)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ones and 3-arylimino-6,7-dihydroimidazo[2,1-c][1,2,4]thiadiazoles have been synthesized by intramolecular nucleophilic substitution reactions at the electron-deficient sp(2) nitrogen atom of 2-(hydroxyimino)imidazolidine O-sulfonate. The displacement of the sulfate leaving group by both nitrogen and sulfur anionic nucleophiles proceeds exothermically by in-plane S(N)2 sigma nucleophilic substitution.

引用

页码：2387 / 2394

页数：8

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