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 journalArticle

8 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 - 2014

Fingerprint

Isothiocyanates
Thiourea
Cyclization
Derivatives
methacrylamide
allylthiourea
allyl isothiocyanate

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and intramolecular cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea. / Kulakov, I. V.; Nikitina, O. S.; Fisyuk, A. S.; Goncharov, D. S.; Shul'Gau, Z. T.; Gulyaev, A. E.

In: Chemistry of Heterocyclic Compounds, Vol. 50, No. 5, 2014, p. 670-676.

Research output: Contribution to journalArticle

Kulakov, I. V. ; Nikitina, O. S. ; Fisyuk, A. S. ; Goncharov, D. S. ; Shul'Gau, Z. T. ; Gulyaev, A. E. / Synthesis and intramolecular cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea. In: Chemistry of Heterocyclic Compounds. 2014 ; Vol. 50, No. 5. pp. 670-676.
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AU - Kulakov, I. V.

AU - Nikitina, O. S.

AU - Fisyuk, A. S.

AU - Goncharov, D. S.

AU - Shul'Gau, Z. T.

AU - Gulyaev, A. E.

PY - 2014

Y1 - 2014

N2 - 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.

AB - 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.

KW - 1,3-thiazines

KW - 1,3-thiazolines

KW - 3-aminopyridin-2(1H)-ones

KW - intramolecular cyclization

KW - isothiocyanates

KW - thioureas

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