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 | |
| State | Published - Nov 25 2012 |
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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
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 journal › Article
}
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 Oleksandrivna
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 -