Some New Derivatives of 2-Pentenedioic Acid

[img]PDF - Authorized users only
Language: English
506Kb
Title:Some New Derivatives of 2-Pentenedioic Acid
Creators:
Tolman, Vladimír
Sedmera, Petr
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 58, 6, pp. 1430-1436

Abstract

Michael addition of <i>N</i>-acylaminomalonates to propynoic esters led to the (<i>E</i>)-4-acylamino)-4-carboxy-2-pentenedioic triesters <i>IIa - IIf</i>. On deprotection and decarboxylation, these compounds afforded 2-(<i>N</i>-acylamino)-2-pentenedioic acid derivatives <i>IIIa - IIIc</i>. Dimethyl (<i>E</i>)-4-diazo-2-pentenedioate (<i>IV</i>) was prepared by direct transfer of the diazo group. On treatment of <i>IV</i> with 4-toluenesulfonic acid, 2-(4-toluenesulfonyloxy)-2-pentenedioate (<i>V</i>) was formed. Iodination of (<i>E</i>)-2-pentenedioic acid led directly to the 2,4-diododerivative <i>VII</i>. From dimethyl (<i>E</i>)-4-oxo-2-pentenedioate the oximino ester <i>VIIIa</i> and the free oximino acid <i>VIIIb</i> were prepared.

Title:Some New Derivatives of 2-Pentenedioic Acid
Creators:
Tolman, Vladimír
Sedmera, Petr
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:58
Number:6
Page Range:pp. 1430-1436
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19931430UNSPECIFIED
ID Code:261
Item Type:Article
Deposited On:06 Feb 2009 16:59
Last Modified:06 Feb 2009 15:59

Citation

Tolman, Vladimír; Sedmera, Petr (1993) Some New Derivatives of 2-Pentenedioic Acid. Collection of Czechoslovak Chemical Communications, 58 (6). pp. 1430-1436. ISSN 0010-0765

Repository Staff Only: item control page