Stereoselective C(2)-Vinylation of 1-Substituted Imidazoles with 3-Phenyl-2-propynenitrile

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作   者：

Trofimov BA;  Andriyankova LV;  Belyaeva KV;  Mal'kina AG;  Nikitina LP;  Afonin AV;  Ushakov IA; 

作者机构：

Russia;  LP;  AG;  IA] Russian Acad Sci;  Irkutsk 664033;  LV;  KV;  Ushakov;  [Trofimov;  Siberian Branch;  Afonin;  AV;  AE Favorsky Irkutsk Inst Chem;  Andriyankova;  Belyaeva;  Mal'kina;  BA;  Nikitina; 

关键词：

GAMMA-HYDROXYACID NITRILES;  CARBENES;  ANNELATION;  5-LIPOXYGENASE;  INHIBITORS;  IONIC LIQUIDS;  ANTAGONISTS;  DERIVATIVES;  IN-SITU;  3-(1-HYDROXYCYCLOHEXYL)-2-PROPYNENITRILE; 

期刊名称：

The Journal of Organic Chemistry

i s s n：

0022-3263

年卷期：

2008 年 73 卷 22 期

页   码：

9155-9157

页   码：

摘   要：

First examples of direct vinylation of 1-substituted imidazoles at the 2-position of the imidazole nucleus are described. 1-Substituted imidazoles la-e are C(2)-vinylated with 3-phenyl-2-propynenitrile (2) at room temperature without catalyst and solvent to afford 3-(1-organyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitriles 3a-e, mainly (c.a. 95%) as (Z)-isomers, in 56-88% yield. The reaction is likely to involve the zwitterionic intermediates, which prototropically isomerizes to imidazole carbene and eventually undergoes the selective 3,2-shift of the functionalized vinyl substituent.