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
Samo za registrovane korisnike
2013
Autori
Ajaj, IsmailMijin, Dušan
Maslak, Veselin
Brković, Danijela V
Milčić, Miloš
Todorović, Nina
Marinković, Aleksandar
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
Microwave assisted synthesis / Heterocycles / Cyclizations / Ab initio calculations / TautomerismIzvor:
Monatshefte Fur Chemie, 2013, 144, 5, 665-675Izdavač:
- Springer Wien, Wien
Finansiranje / projekti:
- Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.1007/s00706-012-0911-5
ISSN: 0026-9247
WoS: 000317713800012
Scopus: 2-s2.0-84879688241
Institucija/grupa
Tehnološko-metalurški fakultetTY - JOUR AU - Ajaj, Ismail AU - Mijin, Dušan AU - Maslak, Veselin AU - Brković, Danijela V AU - Milčić, Miloš AU - Todorović, Nina AU - Marinković, Aleksandar PY - 2013 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2524 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 EP - 675 IS - 5 SP - 665 VL - 144 DO - 10.1007/s00706-012-0911-5 ER -
@article{ author = "Ajaj, Ismail and Mijin, Dušan and Maslak, Veselin and Brković, Danijela V and Milčić, Miloš and Todorović, Nina and Marinković, Aleksandar", 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", pages = "675-665", number = "5", volume = "144", doi = "10.1007/s00706-012-0911-5" }
Ajaj, I., Mijin, D., Maslak, V., Brković, D. V., Milčić, M., Todorović, N.,& Marinković, A.. (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 I, Mijin D, Maslak V, Brković DV, Milčić M, Todorović N, Marinković A. 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, Mijin, Dušan, Maslak, Veselin, Brković, Danijela V, Milčić, Miloš, Todorović, Nina, Marinković, Aleksandar, "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 . .