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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

Само за регистроване кориснике
2013
Аутори
Ajaj, Ismail A.
Mijin, Dušan
Maslak, Veselin
Brkovic, Danijela
Milčić, Miloš
Todorović, Nina
Marinković, Aleksandar D.
Чланак у часопису (Објављена верзија)
Метаподаци
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Апстракт
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.
Кључне речи:
Microwave assisted synthesis / Heterocycles / Cyclizations / Ab initio calculations / Tautomerism
Извор:
Monatshefte Fur Chemie, 2013, 144, 5, 665-675
Издавач:
  • Springer Wien, Wien
Финансирање / пројекти:
  • Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-172013)

DOI: 10.1007/s00706-012-0911-5

ISSN: 0026-9247

WoS: 000317713800012

Scopus: 2-s2.0-84879688241
[ Google Scholar ]
4
4
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/1346
Колекције
  • Radovi istraživača / Researchers' publications
Институција/група
IHTM
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 . .

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