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 › peer-review

14 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
State	Published - Nov 25 2012
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2012.09.041

Fingerprint Dive into the research topics of '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'. Together they form a unique fingerprint.

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 › peer-review

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.

@article{5fb0fa991ce44b4782c72a6924c87475,

title = "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",

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.",

keywords = "3-Cyanopyridine-2(1H)-thiones, Biginelli dihydropyrimidinones, Cascade reaction, Thorpe-Ziegler reaction",

author = "Lebedyeva, {Iryna O.} and Dotsenko, {Victor V.} and Turovtsev, {Vladimir V.} and Krivokolysko, {Sergey G.} and Povstyanoy, {V'Yacheslav M.} and Povstyanoy, {Mikhaylo V.}",

year = "2012",

month = nov,

day = "25",

doi = "10.1016/j.tet.2012.09.041",

language = "English (US)",

volume = "68",

pages = "9729--9737",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "47",

}

TY - JOUR

T1 - The Thorpe-Ziegler-type reaction of 3-cyanopyridine-2(1H)-thiones with Biginelli 6-bromomethyl-3,4-dihydropyrimidin-2(1H)-ones

T2 - Cascade assembling of tetra- and pentacyclic heterocyclic scaffolds

AU - Lebedyeva, Iryna O.

AU - Dotsenko, Victor V.

AU - Turovtsev, Vladimir V.

AU - Krivokolysko, Sergey G.

AU - Povstyanoy, V'Yacheslav M.

AU - Povstyanoy, Mikhaylo V.

PY - 2012/11/25

Y1 - 2012/11/25

N2 - 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.

AB - 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.

KW - 3-Cyanopyridine-2(1H)-thiones

KW - Biginelli dihydropyrimidinones

KW - Cascade reaction

KW - Thorpe-Ziegler reaction

UR - http://www.scopus.com/inward/record.url?scp=84867537379&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84867537379&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2012.09.041

DO - 10.1016/j.tet.2012.09.041

M3 - Article

AN - SCOPUS:84867537379

VL - 68

SP - 9729

EP - 9737

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 47

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this