Synthesis and chemical properties of 8-aryl-7-acyl-1,6-dimethyl-6-hydroxy-4-cyano-5,6,7,8-tetrahydro-3(2H)- isoquinolinones and isoquinolinethiones

Article abstract of DOI:10.1007/BF01169354

8-Aryl-7-acetyl-1,6-dimethyl-6-hydroxy-4-cyano-5,6,7,8-tetrahydro-3(2H)- isoquinolinones and -isoquinolinethiones and their sodium salts were obtained by the reaction of cyanoacetamide and cyanothioacetamide with 3-aryl-2,4-diacetyl-5-methyl-5-hydroxycyclohexanonesinbasicmedium. 8-Aryl-7-acetyl-6-methoxycarbonyl-1,6-dimethyl-4-cyano-5,6,7,8-tetrahydro-3(2H)- isoquinolinones were obtained by the reaction of acetyl chloride and the above isoquinolinone sodium salts. The reaction of iodoacetamide and the above isoquinolinethione sodium salts yielded 8-aryl-7-acelyl-3-carbamoylmethylthio-1,6-dimethyl-4-cyano-5,6,7,8-tetra- hydroisoquinolines, which were cyclized into 1-amino-6-aryl-7-acetyl-2-carbamoyl-5,8-dimethyl-8-hydroxy-6,7,8,9- tetrahydrothiophene[2,3-c]isoquinolines in basic medium. 1996 Plenum Publishing Corporation.