The Thorpe-Ziegler-type reaction of 3-cyanopyridine-2(1H)-thiones with Biginelli 6-bromomethyl-3,4-dihydropyrimidin-2(1H)-ones: Cascade assembling of tetra- and pentacyclic heterocyclic scaffolds

Iryna Oleksandrivna Lebedyeva, Victor V. Dotsenko, Vladimir V. Turovtsev, Sergey G. Krivokolysko, V'Yacheslav M. Povstyanoy, Mikhaylo V. Povstyanoy

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

3-Cyanopyridine-2(1H)-thiones have been shown to react with Biginelli-type ethyl 4-aryl-6-(bromomethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates upon heating in DMF giving rise to ethyl 4-aryl-6-{[(3-cyanopyridin-2-yl)thio] methyl}-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates. The latter upon treatment with an excess of NaH or t-BuOK in boiling DMF undergo a tandem Thorpe-Ziegler-type heterocyclization to give pyrido[3″,2″:4′, 5′]thieno[2′,3′:5,6]pyrido[4,3-d]pyrimidine derivatives in good yields. Selected compounds were tested for antibacterial and antifungal activity.

Original languageEnglish (US)
Pages (from-to)9729-9737
Number of pages9
JournalTetrahedron
Volume68
Issue number47
DOIs
StatePublished - Nov 25 2012

Fingerprint

Thiones
Scaffolds
Heating
Boiling liquids
Derivatives
pyrido(4,3-d)pyrimidine
3-cyanopyridine

Keywords

  • 3-Cyanopyridine-2(1H)-thiones
  • Biginelli dihydropyrimidinones
  • Cascade reaction
  • Thorpe-Ziegler reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

The Thorpe-Ziegler-type reaction of 3-cyanopyridine-2(1H)-thiones with Biginelli 6-bromomethyl-3,4-dihydropyrimidin-2(1H)-ones : Cascade assembling of tetra- and pentacyclic heterocyclic scaffolds. / Lebedyeva, Iryna Oleksandrivna; Dotsenko, Victor V.; Turovtsev, Vladimir V.; Krivokolysko, Sergey G.; Povstyanoy, V'Yacheslav M.; Povstyanoy, Mikhaylo V.

In: Tetrahedron, Vol. 68, No. 47, 25.11.2012, p. 9729-9737.

Research output: Contribution to journalArticle

Lebedyeva, Iryna Oleksandrivna ; Dotsenko, Victor V. ; Turovtsev, Vladimir V. ; Krivokolysko, Sergey G. ; Povstyanoy, V'Yacheslav M. ; Povstyanoy, Mikhaylo V. / The Thorpe-Ziegler-type reaction of 3-cyanopyridine-2(1H)-thiones with Biginelli 6-bromomethyl-3,4-dihydropyrimidin-2(1H)-ones : Cascade assembling of tetra- and pentacyclic heterocyclic scaffolds. In: Tetrahedron. 2012 ; Vol. 68, No. 47. pp. 9729-9737.
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