Chlorine- and sulphur-substituted pyrrolo[ 3,4-b]quinolines and related derivatives arising from the aminolysis of 3,3,9-trichlorothieno[3,4-b]quinolin-1(3H)-one

The outcome from aminolysis of 3,3,9-trichlorothieno[3,4-b] quinolinone with an alkylamine is dependent on the reaction conditions and extraneous reagents employed. A variety of hitherto unreported products can be obtained and include 4- chloro-2-alkylthiocarbamoyl-quinoline-3-carboxylic acid alkylamides, 9-chloro-2-alkyl-3-alkylimino-pyrrolo[3,4-b] quinolines, 9-chloro-2-alkyl-3-thioxo-pyrrolo[ 3,4- b]-quinolines, 2-alkyl-3-alkylimino-9-thioxo-pyrrolo[ 3,4- b] quinolines, and 2-alkyl-9-alkylamino-3-alkylimino-pyrrolo[3,4- b] quinolines. The spectral (H-1 NMR, HRMS) and chemical properties and the structures of the products are described and discussed, and possible mechanistic pathways leading to their formation are presented.