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.
N1 - Copyright:
Copyright 2012 Elsevier B.V., All rights reserved.
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
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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 -