Abstract
The reaction of ethoxymethyleneoxaloacetic ester with phenylhydrazine and methylhydrazine has been studied. It has been established that the addition of phenylhydrazine takes place to the ethoxy group through the β-nitrogen atom, and the addition of methylhydrazine to the ethoxy group predominantly through the α-nitrogen atom. Several derivatives of β-alkyl(aryl)hydrazinomethyleneoxaloacetic esters have been obtained. A series of bis(methylamides) and several diamides of 1-alkyl(aryl)pyrazoledicarboxylic acids have been synthesized. Their structure has been determined on the basis of their UV spectra and their breakdown by hydrolysis to known acids. It has been found that in the alkylation of an ester of 3,4-pyrazoledicarboxylic acid with alkyl halides followed by amidation, two isomeric bis(methylamide)s are formed, apparently with the predominance of derivatives of 1-alkyl-3, 4-pyrazoledicarboxylic acids. It has been established that the bis(methylamide)s of 1-alkyl-3,4-pyrazoledicarboxylic and of 1-alkyl-4, 5-pyrazoledicarboxylic acids have characteristic UV spectra differing from one another. The bis(methylamide)s obtained are pharmacologically active substances.
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Vinogradova, N.B., Khromov -Borisov, N.V. Synthesis and mechanism of the formation of bis(methylamides) of pyrazoledicarboxylic acids. Chem Heterocycl Compd 4, 502–507 (1971). https://doi.org/10.1007/BF00486771
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DOI: https://doi.org/10.1007/BF00486771