A Domino Reaction of α,β-Acetylenic γ-Hydroxy Nitriles with Arenecarboxylic Acids: An Unexpected Facile Shortcut to 4-Cyano-3(2H)-furanones

被引：34
|
作者：
Trofimov, Boris A. [1 ]
Shemyakina, Olesya A. [1 ]
Mal'kina, Anastasiya G. [1 ]
Ushakov, Igor' A. [1 ]
Kazheva, Olga N. [2 ]
Alexandrov, Grigorii G. [3 ]
Dyachenko, Oleg A. [2 ]
机构：
[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, 1 Favorsky Str, Irkutsk 664033, Russia
[2] Russian Acad Sci, Inst Problems Chem Phys, Chernogolovka 142432, Russia
[3] Russian Acad Sci, NS Kurnakov Gen & Inorgan Chem Inst, Moscow 119991, Russia
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 14期
基金：
俄罗斯基础研究基金会;
关键词：
GEIPARVARIN ANALOGS; CARBOXYLIC-ACIDS; JATROPHONE; DERIVATIVES; ALKYNES; CYCLIZATION; INHIBITORS; 3(2H)-FURANONES; ACCESS; ESTERS;
D O I：
10.1021/ol1011532
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An unexpected facile domino reaction of alpha,beta-acetylenic gamma-hydroxy nitriles with arenecarboxylic acids (Et3N, MeCN, 20-25 degrees C, 48 h) affords 4-cyano-3(2H)-furanones in 67-86% yield. The reaction is triggered by the addition of an arenecarboxylic acid to a triple bond, followed by the domino reaction sequence: intramolecular transesterification-enol formation and Claisen condensation of the ketoacetonitrile tautomer with ester functional group.
引用
收藏
页码：3200 / 3203
页数：4
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