94341-89-6Relevant academic research and scientific papers
Continuous flow synthesis of some 6- And 1,6-substituted 3-cyano-4-methyl-2-pyridones
Tadi?, Julijana,Mihajlovi?, Marina,Jovanovi?, Mi?a,Mijin, Du?an
, p. 531 - 538 (2019/08/30)
In this study, six 6- and 1,6-substituted-3-cyano-4-methyl-2-pyri-dones were synthesized in a continuous flow microreactor system. The syntheses were realized at room temperature and the obtained results were compared to those achieved within classical syntheses. In order to optimize the continuous flow syntheses and increase the yield of the products, the retention time in the microreactor was varied by changing the flow rates of the reactant solutions. Furthermore, the reaction was optimized for 3-cyano-4,6-dimethyl-2-pyridone and 3-cyano-6-hydroxy-4-methyl-2-pyridone, which are comercially important in the pharmaceutical and dye industries. Both 2-pyridones were obtained in satisfactory yield of circa 60 % in less than 10 min. The resulting compounds were characterized by their melting points, FT-IR, 1H-NMR and UV–Vis spectra. The efficiency of the presented method for the synthesis of 2-pyridone-based molecules has promising potential for industrial production.
Ionic liquid catalyzed 4,6-disubstituted-3-cyano-2-pyridone synthesis under solvent-free conditions
Chavan, Sunil S.,Degani, Mariam S.
experimental part, p. 1693 - 1697 (2012/03/11)
A green protocol for the synthesis of 4,6-disubstituted-3-cyano-2-pyridones from cyanoacetamides and 1,3-dicarbonyl compounds or chalcones using guanidine based ionic liquid as catalyst has been developed. In solvent-free conditions at 30 °C, [TMG][Lac] (1,1,3,3-tetramethylguanidine lactate) was found to have the highest catalytic activity among the ionic liquids including [TMG][Ac] (1,1,3,3-tetramethylguanidine acetate), [TMG][Pr] (1,1,3,3-tetramethylguanidine propionate), [TMG][n-Bu] (1,1,3,3-tetramethylguanidine n-butyrate) and [TMG][TFA] (1,1,3,3-tetramethylguanidine trifluoroacetate). The catalyst was recovered and recycled several times without significant loss of catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]
Synthesis of N-substituted 4,6-dimethyl-3-cyano-2-pyridones under microwave irradiation
Mijin, Du?an,Marinkovi?, Aleksandar
, p. 193 - 198 (2007/10/03)
N-substituted 4,6-dimethyl-3-cyano-2-pyridones have been prepared from acetylacetone, N-substituted cyanoacetamide, and pyperidine as catalyst under microwave irradiation without solvent. The rapid and simple method produced pure products in high yields. Copyright Taylor & Francis LLC.
Synthesis of substituted 3-cyano-2-pyridones: Part IV - Influence of 3-alkyl-2,4-pentanedione and N-alkyl cyanoacetamide structure on the enzyme catalyzed synthesis of substituted 3-cyano-2-pyridones
Mijin, Du?an ?.,Mili?, Branislav D.,Mi?i?-Vukovi?, Milica M.
, p. 993 - 1003 (2007/10/03)
Lipase from Candida rugosa has been used to study the influence of 3-alkyl-2,4-pentanedione and N-alkyl cyanoacetamide structure on the enzyme catalyzed reaction of pyridone ring formation in water at 40°C. Starting with 1,3-diketones and cyanoacetamides and for comparison, the expected corresponding substituted 3-cyano-2-pyridones have been synthesized by chemical methods. Bulkier substitueras lower the initial reaction rate of the enzyme catalyzed reactions and consequently the yield of the corresponding pyridones. N-alkyl cyanoacetamides are more reactive in comparison to the corresponding 3-alkyl-2,4-pentanediones with respect to the obtained yields of the corresponding substituted 3-cyano-2-pyridones.
