Highly efficient synthesis of polyfluorinated 2-mercaptobenzothiazole derivatives

Larisa Politanskaya, Zequn Duan, Irina Bagryanskaya, Ilia Eltsov, Evgeny Tretyakov, Chanjuan Xi

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

A convenient and efficient method for the synthesis of polyfluorinated 2-mercaptobenzothiazoles from the corresponding aniline derivatives and CS2, mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in toluene is described. The reaction proceeded via nucleophilic attack at the carbon atom of carbon disulfide by the nitrogen atom of NH2-group in arene followed by selective intramolecular fluorine atom substitution in the ortho-position to the amino group. This synthetic methodology could be used to prepare fluorinated 2-mercaptobenzothiazole containing alkynyl group in good to excellent yields. The reaction takes place under very mild reaction conditions (50 °C) and uses readily available starting materials.

Original languageEnglish
Pages (from-to)130-136
Number of pages7
JournalJournal of Fluorine Chemistry
Volume212
DOIs
Publication statusPublished - 1 Aug 2018

Keywords

  • 2-Mercaptobenzothiazoles
  • Polyfluorinated anilines
  • Polyfluorinated heterocycles
  • Reaction mechanism
  • Tandem reaction
  • CRYSTAL-STRUCTURE
  • CARBON-DISULFIDE
  • O-HALOANILINES

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