SYNTHESIS AND ELECTROCHEMICAL OXIDATION OF NITRILES OF 4-ARYL-2-CARBAMOYLMETHYLTHIO-5-ETHOXYCARBONYL-1,4-DIHYDROPYRIDINE-3-CARBOXYLIC ACIDS
Keywords:
6-hydroxy-1,4,5,6-tetrahydropyridines, 1,4-dihydropyridines, one-reactor three-component synthesis, electrochemical oxidationAbstract
Nitriles of 4-aryl-2-carbamoylmethylthio-5-ethoxycarbonyl-6-hydroxy-1,4,5,6-tetrahydropyridine-3-carboxylic acids were obtained by the alkylation of 1,4,5,6-tetrahydropyridine-2-thiolate with iodoacetamide or by a three-component synthesis by condensing 2-arylmethylene-1,3-dicarbonyl compounds with 2-cyanothioacetamide in the presence of piperidine with subsequent reaction with iodoacetamide. Nitriles of 4-aryl-2-carbamoylmethylthio-5-ethoxycarbonyl-1,4-dihydropyridine-3-carboxylic acids were obtained by the dehydration of 6-hydroxy-1,4,5,6-tetrahydropyridines or with a one-reactor three-component system from 2-cyano-3-(4-methoxyphenyl)thioacrylamide, 1,3-dicarbonyl compounds, and iodoacetamide. The electrochemical oxidation of the synthesized nitriles was investigated and it was established that derivatives of 1,4,5,6-tetrahydropyridine as a rule are oxidized readily to the corresponding 1,4-dihydropyridines. A comparative analysis has been carried out of the ability of hydrogenated pyridines to be oxidized electrochemically depending on the electron-withdrawing properties of the substituents in the heterocycle.
How to Cite
Baumane, L.; Krauze, A.; Chernova, L.; Sile, L.; Duburs, G.; Stradins, J. Chem. Heterocycl. Compd. 2003, 39, 1591. [Khim. Geterotsikl. Soedin. 2003, 1808.]
For this article in the English edition, see DOI 10.1023/B:COHC.0000018336.52691.a7
