Chemistry of Heterocyclic Compounds

, Volume 32, Issue 3, pp 319–322 | Cite as

Synthesis and reactions of esters of 3-cyano-2-OXO-5,6-tri(tetra)methylene-1,2-dihydroisonicotinic and 2-amino-3-Ethoxycarbonyl-5,6-tri(tetra)-methyleneisonicotinic acids

  • T. A. Smirnova
  • M. Yu. Gavrilov


Esters of 3-cyano-2-oxo-5, 6-tri (tetra)-methylene-1, 2-dihydroisonicotinic and 2-amino-3-ethoxycarbonyl-5, 6-tri (tetra)methyleneisorticotinic acids have been obtained by the reaction of 2-oxocyclopentyl(hexyl)glyoxylic acid esters with malonic acid derivatives. Boiling the esters containing a tetramethylene ring with 75% sulfuric acid gave hydrolysis of the ester and cyano groups to carboxyl with subsequent decarboxylation at the 3 position and the formation of 2-oxo-5, 6-tetramethylene-1, 2-dihydroisonicotinic acid (2-oxo-1, 2, 5, 6, 7, 8-hexahydroquinoline-4-carboxylic acid).


Ester Hydrolysis Organic Chemistry Carboxyl Sulfuric Acid 
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© Plenum Publishing Corporation 1996

Authors and Affiliations

  • T. A. Smirnova
  • M. Yu. Gavrilov

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