共 21 条
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
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.
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页码:3200 / 3203
页数:4