oa South African Journal of Chemistry - 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.


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