Synthesis and intramolecular cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea

I. V. Kulakov, O. S. Nikitina, A. S. Fisyuk, D. S. Goncharov, Z. T. Shul'Gau, A. E. Gulyaev

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

The reaction of 3-amino-4,6-dimethylpyridin-2(1H)-one and 3-amino-4-phenylpyridin-2-one with acyl isothiocyanates (benzoyl-, 4-bromobenzoyl-, and methacryloyl isothiocyanates) and with allyl isothiocyanate has been studied. The N-carbamothioyl methacrylamides and N-allylthioureas obtained undergo intramolecular heterocyclization reactions to give the corresponding 1,3-thiazin-4-one and 1,3-thiazoline derivatives. It was found that the starting 3-amino-4,6-dimethylpyridin-2(1H)-one shows antiradical activity but the synthesized thioureas do not.

Original languageEnglish
Pages (from-to)670-676
Number of pages7
JournalChemistry of Heterocyclic Compounds
Volume50
Issue number5
DOIs
Publication statusPublished - Aug 2014

Keywords

  • 1,3-thiazines
  • 1,3-thiazolines
  • 3-aminopyridin-2(1H)-ones
  • intramolecular cyclization
  • isothiocyanates
  • thioureas

ASJC Scopus subject areas

  • Organic Chemistry

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