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 (1H 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. (South African Journal of Chemistry: 2003 56: 40-46