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A simple and convenient synthesis of tautomeric (6 or 2)-hydroxy-4-methyl-(2 or 6)-oxo-1-(substituted phenyl)-(1,2 or 1,6)-dihydropyridine-3-carbonitriles
A simple and convenient synthesis of tautomeric (6 or 2)-hydroxy-4-methyl-(2 or 6)-oxo-1-(substituted phenyl)-(1,2 or 1,6)-dihydropyridine-3-carbonitriles from ethyl acetoacetate and 2-cyano-N-(substituted phenyl)ethanamides using microwave-assisted chemistry is presented. The structure of the obtained product was confirmed by the use of FT-IR, NMR, UV, and MS techniques. The presence of tautomeric forms (6-hydroxy-4-methyl-2-oxo-1-(substituted phenyl)-1,2-dihydropyridine-3-carbonitrile and 2-hydroxy-4-methyl-6-oxo-1-(substituted phenyl)-1,6-dihydropyridine-3-carbonitrile) and the state of equilibrium of the obtained product in DMSO-d (6) was studied by H-1 and C-13 NMR spectroscopy, as well as B3LYP/6-311++G(d,p) and GIAO/WP04/aug-cc-pVDZ theoretical calculations.
Keywords:
Microwave assisted synthesis / Heterocycles / Cyclizations / Ab initio calculations / Tautomerism
TY - JOUR
AU - Ajaj, Ismail A.
AU - Mijin, Dušan
AU - Maslak, Veselin
AU - Brkovic, Danijela
AU - Milčić, Miloš
AU - Todorović, Nina
AU - Marinković, Aleksandar D.
PY - 2013
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1346
AB - A simple and convenient synthesis of tautomeric (6 or 2)-hydroxy-4-methyl-(2 or 6)-oxo-1-(substituted phenyl)-(1,2 or 1,6)-dihydropyridine-3-carbonitriles from ethyl acetoacetate and 2-cyano-N-(substituted phenyl)ethanamides using microwave-assisted chemistry is presented. The structure of the obtained product was confirmed by the use of FT-IR, NMR, UV, and MS techniques. The presence of tautomeric forms (6-hydroxy-4-methyl-2-oxo-1-(substituted phenyl)-1,2-dihydropyridine-3-carbonitrile and 2-hydroxy-4-methyl-6-oxo-1-(substituted phenyl)-1,6-dihydropyridine-3-carbonitrile) and the state of equilibrium of the obtained product in DMSO-d (6) was studied by H-1 and C-13 NMR spectroscopy, as well as B3LYP/6-311++G(d,p) and GIAO/WP04/aug-cc-pVDZ theoretical calculations.
PB - Springer Wien, Wien
T2 - Monatshefte Fur Chemie
T1 - A simple and convenient synthesis of tautomeric (6 or 2)-hydroxy-4-methyl-(2 or 6)-oxo-1-(substituted phenyl)-(1,2 or 1,6)-dihydropyridine-3-carbonitriles
VL - 144
IS - 5
SP - 665
EP - 675
DO - 10.1007/s00706-012-0911-5
ER -
@article{
author = "Ajaj, Ismail A. and Mijin, Dušan and Maslak, Veselin and Brkovic, Danijela and Milčić, Miloš and Todorović, Nina and Marinković, Aleksandar D.",
year = "2013",
abstract = "A simple and convenient synthesis of tautomeric (6 or 2)-hydroxy-4-methyl-(2 or 6)-oxo-1-(substituted phenyl)-(1,2 or 1,6)-dihydropyridine-3-carbonitriles from ethyl acetoacetate and 2-cyano-N-(substituted phenyl)ethanamides using microwave-assisted chemistry is presented. The structure of the obtained product was confirmed by the use of FT-IR, NMR, UV, and MS techniques. The presence of tautomeric forms (6-hydroxy-4-methyl-2-oxo-1-(substituted phenyl)-1,2-dihydropyridine-3-carbonitrile and 2-hydroxy-4-methyl-6-oxo-1-(substituted phenyl)-1,6-dihydropyridine-3-carbonitrile) and the state of equilibrium of the obtained product in DMSO-d (6) was studied by H-1 and C-13 NMR spectroscopy, as well as B3LYP/6-311++G(d,p) and GIAO/WP04/aug-cc-pVDZ theoretical calculations.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "A simple and convenient synthesis of tautomeric (6 or 2)-hydroxy-4-methyl-(2 or 6)-oxo-1-(substituted phenyl)-(1,2 or 1,6)-dihydropyridine-3-carbonitriles",
volume = "144",
number = "5",
pages = "665-675",
doi = "10.1007/s00706-012-0911-5"
}
Ajaj, I. A., Mijin, D., Maslak, V., Brkovic, D., Milčić, M., Todorović, N.,& Marinković, A. D.. (2013). A simple and convenient synthesis of tautomeric (6 or 2)-hydroxy-4-methyl-(2 or 6)-oxo-1-(substituted phenyl)-(1,2 or 1,6)-dihydropyridine-3-carbonitriles. in Monatshefte Fur Chemie
Springer Wien, Wien., 144(5), 665-675.
https://doi.org/10.1007/s00706-012-0911-5
Ajaj IA, Mijin D, Maslak V, Brkovic D, Milčić M, Todorović N, Marinković AD. A simple and convenient synthesis of tautomeric (6 or 2)-hydroxy-4-methyl-(2 or 6)-oxo-1-(substituted phenyl)-(1,2 or 1,6)-dihydropyridine-3-carbonitriles. in Monatshefte Fur Chemie. 2013;144(5):665-675.
doi:10.1007/s00706-012-0911-5 .
Ajaj, Ismail A., Mijin, Dušan, Maslak, Veselin, Brkovic, Danijela, Milčić, Miloš, Todorović, Nina, Marinković, Aleksandar D., "A simple and convenient synthesis of tautomeric (6 or 2)-hydroxy-4-methyl-(2 or 6)-oxo-1-(substituted phenyl)-(1,2 or 1,6)-dihydropyridine-3-carbonitriles" in Monatshefte Fur Chemie, 144, no. 5 (2013):665-675,
https://doi.org/10.1007/s00706-012-0911-5 . .
