Highly efficient synthesis of novel fluorinated 3-amino-2-mercaptobenzothiazole-2(3H)-thione derivatives

Larisa Politanskaya, Irina Bagryanskaya, Evgeny Tretyakov, Chanjuan Xi

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Here, a convenient and efficient method for the synthesis of polyfluorinated 3-amino-2-mercaptobenzothiazole-2(3H)-thione derivatives from the corresponding arylhydrazines and CS2, mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in acetonitrile is described. The reaction proceeded via selective intramolecular ortho-fluorine atom substitution by the S-nucleophilic center of the carbon disulfide molecule attached at the first stage of the reaction (a tandem process). The reaction takes place under mild reaction conditions (room temperature), has an excellent yield, and involves readily available starting materials.

Original languageEnglish
Article number109628
Number of pages10
JournalJournal of Fluorine Chemistry
Volume239
DOIs
Publication statusPublished - Nov 2020

Keywords

  • C-F activation
  • Fluorinated mercaptobenzothiazole derivatives
  • Fluorinated S,N-heterocycles
  • Polyfluorinated arylhydrazines
  • Tandem reaction
  • BENZOTHIAZOLE
  • POTENT
  • CRYSTAL-STRUCTURE
  • CYTOTOXICITY EVALUATION
  • BIOLOGICAL EVALUATION

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