Collect. Czech. Chem. Commun.
1993, 58, 1430-1436
https://doi.org/10.1135/cccc19931430
Some New Derivatives of 2-Pentenedioic Acid
Vladimír Tolmana and Petr Sedmerab
a Institute of Nuclear Biology and Radiochemistry, Academy of Sciences of the Czech Republic, 142 20 Prague 4, Czech Republic
b Institute Microbiology, Academy of Sciences of the Czech Republic, 142 20 Prague 4, Czech Republic
Abstract
Michael addition of N-acylaminomalonates to propynoic esters led to the (E)-4-acylamino)-4-carboxy-2-pentenedioic triesters IIa - IIf. On deprotection and decarboxylation, these compounds afforded 2-(N-acylamino)-2-pentenedioic acid derivatives IIIa - IIIc. Dimethyl (E)-4-diazo-2-pentenedioate (IV) was prepared by direct transfer of the diazo group. On treatment of IV with 4-toluenesulfonic acid, 2-(4-toluenesulfonyloxy)-2-pentenedioate (V) was formed. Iodination of (E)-2-pentenedioic acid led directly to the 2,4-diododerivative VII. From dimethyl (E)-4-oxo-2-pentenedioate the oximino ester VIIIa and the free oximino acid VIIIb were prepared.
