T. Smirnova, M. Y. Gavrilov, M. V. Vasilyuk
2006
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Journal
Pharmaceutical Chemistry Journal
Abstract
[ H I Previously we have reported on a series ofalkyland arylamides of 1,2-dihydro-2-oxocinchoninic acid possessing antiinflammatory and analgesic activity [1, 2]. There is a group of structurally close 2-oxoi,2,5,6,7,8-hexahydroquinoline-4carboxylic acid amides which have not been studied in this respect until now. In searching for new antiinflammatory agents, we have synthesized and characterized a series of these compounds. The investigation showed that acid I interacts with amines in the presence of phosphorus oxychloride, with the formation of substituted 2-oxo-l,2,5,6,7,8-hexahydroquinoline-4-carboxylic acid amides (IIa-lie). Amides II can be readily methylated at the heterocyclic nitrogen by reaction with methyl iodide in an alkaline medium, which is demonstrated below by the synthesis of derivatives Illa and IIIb. The proposed structures were confirmed by IR and IH NMR spectroscopic data.