16232-42-1Relevant academic research and scientific papers
Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl- 5-(3-and 4-substituted phenylazo)-2-pyridones
Alimmari, Adel S.,Marinkovic, Aleksandar D.,Mijin, Dusan Z.,Valentic, Natasa V.,Todorovic, Nina,Uscumlic, Gordana S.
, p. 1019 - 1032 (2010)
A series of some new pyridone arylazo dyes was synthesized from the corresponding diazonium salts and 3-cyano-4,6-diphenyl-2-pyridone using the classical reaction for the synthesis of the azo compounds. The structures of these dyes were confirmed by UV-Vis, FT-IR and 1H-NMR spectroscopic techniques. The solvatochromism of the dyes was evaluated with respect to visible absorption properties in various solvents. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The 2-pyridone/2-hydroxypiridine tautomeric equilibration was found to depend on the substituents as well as on the solvents.
Synthesis and spectroscopic properties of pyridones - Experimental and theoretical insight
Nawaz,Hisaindee,Graham,Rauf,Saleh
, p. 51 - 59 (2014)
Cyano pyridone (CPy) and its substituted derivatives OCH3 and NO2) were synthesized and their absorption spectra were examined in different solvents. The absorption spectra of CPy in different solvents indicated a dependence on the polarizability of the solvent. NMR studies of the keto and enol equilibrium in CPy revealed temperature dependence, with the keto form being more predominant. The equilibrium constant values were in agreement with the theoretical calculations. The calculated pKa value for CPy was found to be 9.50 ± 0.57, whereas, for the nitro and methoxy substituted CPy, the values were 8.52 ± 0.36 and 11.04 ± 0.21 respectively. In mixed solvent systems, the preferential solvation was observed in DMSO/CH2Cl2 mixtures, whereas in DMSO/i-PrOH, the mixture behaved ideally. The calculations using the PCM model indicated ΔG values favoring the keto form in both dichloromethane and DMSO. The calculated transition energies were found to be higher than those observed experimentally. For each compound, the keto form was predicted to absorb at a lower energy than the enol form. The main transition of both forms of CPy corresponded to a π-π* transition from the HOMO → LUMO of the compound.
2-Pyridones from cyanoacetamides and enecarbonyl compounds: Application to the synthesis of nothapodytine B
Carles, Lionel,Narkunan, Kesavaram,Penlou, Sebastien,Rousset, Laurence,Bouchu, Denis,Ciufolini, Marco A.
, p. 4304 - 4308 (2002)
The condensation of an enone or enal with cyanoacetamide derivatives and t-BuOK furnishes either 3-cyano-2-pyridones or 3-unsubstituted-2-pyridones, depending on whether the reaction is carried out in the presence or in the absence of O2. In the first case, in situ oxidation of Michael-type intermediates takes place; in the second case, the products result from "decyanidative aromatization" of such intermediates. A one-step synthesis of 3-alkyl-2-pyridones has been devised on the basis of decyanative union of an enone/enal and a 2-alkylcyanoacetamide. The new reaction forms the centerpiece of an unusually concise synthesis of nothapodytine B (mappicine ketone).
One-Pot Sequential Synthesis of Fused Isoquinolines via Intramolecular Cyclization/Annulation and their Photophysical Investigation
Rakshit, Amitava,Sau, Prasenjit,Ghosh, Subhendu,Patel, Bhisma K.
, p. 3824 - 3836 (2019)
One of the cyano group of γ-keto malononitrile gets hydrolyzed selectively to an amide in the presence of copper(II) acetate monohydrate. The in situ generated amide undergo an intramolecular dehydrative cyclization to a 1,2-dihydropyridone intermediate.
KAl(SO4)2·12H2O catalyzed efficient synthesis of 3,4,6-trisubstituted 2-pyridone in water
Heravi, Majid M.,Oskooie, Hossein A.,Karimi, Narges,Hamidi, Hoda
, p. 1059 - 1062 (2011)
An efficient green protocol for the preparation 3,4,6-trisubstituted 2-pyridone of employing a condensation reaction of cyanoacetamide and acetylacetone in the presence of KAl(SO4)2·12H 2O in water has been described. The present procedure offers advantage such as shorter reaction time, simple workup, and excellent yields.
Utilization of cyanopyridine in design and synthesis of first-in-class anticancer dual acting PIM-1 kinase/HDAC inhibitors
Bass, Amr K.A.,Nageeb, El-Shimaa M.,El-Zoghbi, Mona S.,Mohamed, Mamdouh F.A.,Badr, Mohamed,Abuo-Rahma, Gamal El-Din A.
, (2021/12/27)
Herein, we report design and synthesis of twenty-one dual PIM-1/HDAC inhibitors utilizing 3-cyanopyridines as a novel cap moiety linked with aliphatic /aromatic linker bearing carboxylic acid 3a-g, hydroxamic acid 4a-g or 2-aminoanilide moieties 5a-g as z
Cyano-azobenzene compound and application thereof and Contains organic electroluminescent device of this compound
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Paragraph 0053-0055, (2021/08/25)
and Contains the organic electroluminescent device of the compound, and the cyanazine compound has the structure of the formula (1), wherein X. 1 -X5 Each is independently represented C or N. Moreover X. 1 -X5 There 1 - 3 were chosen to N. Cyano groups only at X1 -X5 The substitution is performed at the time of a carbon atom, and the cyano group is at X. 1 -X5 The number is 1 - 3 integer. , The sum ≤ 5 of the number of nitrogen atoms and cyano groups. The formula (2) represents Ar structures. The compound is used as a host material, an electron transport material, a hole blocking material or an electron injection material of an organic electroluminescence device, and the energy level of HOMO and LUMO can be easily adjusted according to the asymmetric structure.
Synthesis of new substituted pyridine derivatives as potent anti-liver cancer agents through apoptosis induction: In vitro, in vivo, and in silico integrated approaches
Boraei, Ahmed T.A.,Eltamany, Elsayed H.,Ali, Ibrahim A.I.,Gebriel, Sara M.,Nafie, Mohamed S.
, (2021/04/27)
Liver cancer is the most common type of cancer in many countries. New studies and statistics show rising liver cancer worldwide, so it is essential to seek new agents for this type of cancer. PIM1 has an attractive target in the discovery of cancer medica
Synthesis and anticancer properties of novel hydrazone derivatives incorporating pyridine and isatin moieties
Zebbiche, Zineddine,Tekin, Suat,Kü?ükbay, Hasan,Yüksel, Furkan,Boumoud, Boudjemaa
, (2020/12/29)
Nine novel hydrazone derivatives (4a–i) incorporating pyridine and isatin moieties were synthesized through one-pot, four-component heterocyclic condensation reactions. The structures of all new compounds (2a–e, 3a, 3c–e, and 4a–e) were identified by sup
2-(Substituted amino)-8-Azachromones from 4,6-Diaryl-2-pyridones: A Synthetic Strategy toward Compounds of Broad Structural Diversity
Saulnier, Steve,Ghoteimi, Rayane,Mathé, Christophe,Peyrottes, Suzanne,Uttaro, Jean-Pierre
, p. 11778 - 11793 (2020/10/23)
3-Acetoacetyl-4,6-diaryl-2-pyridones are synthesized in three steps from chalcones and then condense with carbon disulfide to afford 8-Azachromones containing a methylthio group at C2. This leaving group offers an entry point for the insertion of more com
