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

Theodorus Van Es, Benjamin Staskun*

*Corresponding author for this work

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    5 Citations (Scopus)

    Abstract

    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]quino-lines, 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.

    Original languageEnglish
    Pages (from-to)40-46
    Number of pages7
    JournalSouth African Journal of Chemistry
    Volume56
    Publication statusPublished - 5 Aug 2003

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