I. V. Dyachenko, M. V. Vovk
Jun 8, 2013
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0
Influential Citations
3
Citations
Journal
Russian Journal of Organic Chemistry
Abstract
Derivatives of partially hydrogenated 3-thioxoisoquinoline-4-carboxylic acids are a promising type of heterocyclic synthons. For instance, their nitriles easily obtained from 2-acylcyclohexanons and cyanothioacetamide [1] are used as semiproducts in the synthesis of HIV-1 reverse transcriptase [2], antimicrobial preparations [3], substances with the fungicidal [4] and cardiotonic action [5]. We recently synthesized the corresponding amides by condensation of 1-amino-2-acylcycloalkenes with monothiomalonodiamide [6]. The esters of these acids were not described. We describe here a convenient method of the synthesis of ethyl 3-thioxo-1-phenyl-2,3,5,6,7,8-hexahydroisoquinoline-4-carboxylate (I) consisting in the reaction of 1-benzoyl-2-(morpholin-4-yl)cyclohexene (II) [6] with ethyl 3-amino-3-thioxopropanoate (III) in anhydrous ethanol at 20°C in the presence of sodium ethylate. The alkylation of compound I with N-(4-bromophenyl)2-chloroacetamide (IV) in DMF in the presence of alkali resulted in the formation of the corresponding thioester ethyl 3-[2-(4-bromophenylamino)-2-oxo-ethylsulfanyl]1-phenyl-5,6,7,8-tetrahydroisoquinoline-4-carboxylate (V) in keeping with the general rules of the chemistry of 3-thioxo-2,3,5,6,7,8-hexahydroisoquinolines [7].