Chemo-, regio- and stereospecific addition of amino acids to acylacetylenes: a facile synthesis of new N-acylvinyl derivatives of amino acids

被引：25

作者：

Glotova, Tatyana E. ^{[1
]}

Dvorko, Marina Yu. ^{[1
]}

Ushakov, Igor A. ^{[1
]}

Chipanina, Nina N. ^{[1
]}

Kazheva, Olga N. ^{[2
]}

Chekhlov, Anatolii N. ^{[2
]}

Dyachenko, Oleg A. ^{[2
]}

Gusarova, Nina K. ^{[1
]}

Trofimov, Boris A. ^{[1
]}

机构：

[1] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, Irkutsk 664033, Russia

[2] Russian Acad Sci, Inst Problems Chem Phys, Chernogolovka 142432, Russia

来源：

TETRAHEDRON | 2009年 / 65卷 / 47期

关键词：

Amino acids; Acylacetylenes; N-Acylvinyl derivatives of amino acids; Nucleophilic addition; BETA-ENAMINONES; ONE-POT; COMPLEXES; CRYSTAL; CONDENSATION; HETEROCYCLES; CONVENIENT; KETONES; COPPER;

D O I：

10.1016/j.tet.2009.09.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The one-pot reaction of natural amino acids (glycine, beta-alanine, gamma-aminobutyric and epsilon-aminocapronic acids, D,L-valine, D,L-leucine, anthranilic acid) with bielectrophilic acylacetylenes proceeds chemo-, regio- and stereospecifically in the presence of NaOH (45-50 degrees C, 4 h, EtCH-H2O) to give (after treatment of the reaction mixture with aqueous HCl) Z-isomers of N-acylvinylderivatives of amino acids in 87-94% yield. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：9814 / 9818

页数：5

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