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 O. Lebedyeva; Victor V. Dotsenko; Vladimir V. Turovtsev; Sergey G. Krivokolysko; V'Yacheslav M. Povstyanoy; Mikhaylo V. Povstyanoy

doi:10.1016/j.tet.2012.09.041

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

Research output: Contribution to journal › Article

13 Scopus citations

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 language	English (US)
Pages (from-to)	9729-9737
Number of pages	9
Journal	Tetrahedron
Volume	68
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2012.09.041
Publication status	Published - Nov 25 2012
Externally published	Yes

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Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Lebedyeva, I. O., Dotsenko, V. V., Turovtsev, V. V., Krivokolysko, S. G., Povstyanoy, VY. M., & Povstyanoy, M. V. (2012). 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. Tetrahedron, 68(47), 9729-9737. https://doi.org/10.1016/j.tet.2012.09.041

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 O.; 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 journal › Article

Lebedyeva, IO, Dotsenko, VV, Turovtsev, VV, Krivokolysko, SG, Povstyanoy, VYM & Povstyanoy, MV 2012, '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', Tetrahedron, vol. 68, no. 47, pp. 9729-9737. https://doi.org/10.1016/j.tet.2012.09.041

Lebedyeva IO, Dotsenko VV, Turovtsev VV, Krivokolysko SG, Povstyanoy VYM, Povstyanoy MV. 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. Tetrahedron. 2012 Nov 25;68(47):9729-9737. https://doi.org/10.1016/j.tet.2012.09.041

Lebedyeva, Iryna O. ; 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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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.",

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10.1016/j.tet.2012.09.041