Synthesis of heterocyclic compounds using oxaloacetic ester (review)

Abstract

Published data on the use of oxaloacetic ester in the synthesis of various heterocyclic systems are discussed.Scientists have been engaged in research on the reactions of oxaloacetic ester since the end of the nineteenth century. A large contribution to this field was made by Wislicenus, who extensively studied the chemical transformations of oxaloacetic ester [1]. The interest in oxaloacetic ester was prompted by the presence of four reaction centers in its molecule, making it possible the use it for the production of a large number of different compounds. In this review articles concerning the use of oxaloacetic ester in the synthesis of both monocyclic and condensed heterocyclic compounds are analyzed. OXALOACETIC ESTER IN THE SYNTHESIS OF MONOHETEROCYCLESThere are a large number of reactions in which oxaloacetic ester is used as starting compound in the synthesis of five-membered (furan and pyrrole derivatives) and six-membered (pyridine and pyrimidine derivatives) heterocycles.Thus, for example, oxaloacetic ester (1) undergoes intramolecular ester condensation, forming the dioxo derivative of furan 2 [2]. OEt OEt O O O OEt OH O O OEt O EtO O O 1 2 __________________________________________________________________________________________ M. E. Evsevyev

Method of synthesis and structure of (5E)-5-(2-alkoxy-2-oxoethylidene)-4-hydroxy-2,2-dimethyl-1-(4-methylphenyl)-2,5-dihydro-1H-pyrrole-3-carboxylates

“…pyruvic acids and their esters or oxalylacetates, with aldehydes (ketones) and amines or directly with Schiff bases are successfully used in organic synthesis for the preparation of oxopyrrole derivatives exhibiting diverse biological activity [1][2][3]. Recently, Zykova et al [4,5] erroneously assigned 3,4-dihydro-2H-1,3oxazine structure to the products obtained by reactions of tatraoxo compounds, 1,6-diarylhexane-1,3,4,6-tetraones, with aromatic aldehyde imines.…”