- A phosphine-mediated synthesis of 2,3,4,5-tetra-substituted N-hydroxypyrroles from α-oximino ketones and dialkyl acetylenedicarboxylates under ionic liquid green-media
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Background: The development of multicomponent reactions (MCRs) in the presence of task-specific ionic liquids (ILs), used not only as environmentally benign reaction media, but also as catalysts, is a new approach that meet with the requirements of sustainable chemistry. In recent years, the use of ionic liquids as a green media for organic synthesis has become a chief study area. This is due to their unique properties such as non-volatility, non-flammability, chemical and thermal stability, immiscibility with both organic compounds and water and recyclability. Ionic liquids are used as environmentally friendly solvents instead of hazardous organic solvents. Objective: We report the condensation reaction between α-oximinoketone and dialkyl acetylene dicarboxylate in the presence of triphenylphosphine to afford substituted pyrroles under ionic liquid conditions in good yields. Result: Densely functionalized pyrroles was easily prepared from reaction of α-oximinoketones, dialkyl acetylene dicarboxylate in the presence of triphenylphosphine in a quantitative yield under ionic liquid conditions at room temperature. Conclusion: In conclusion, ionic liquids are indicated as a useful and novel reaction medium for the selective synthesis of functionalized pyrroles. This reaction medium can replace the use of hazardous organic solvents. Easy work-up, synthesis of polyfunctional compounds, decreased reaction time, having easily available-recyclable ionic liquids, and good to high yields are advantages of present method.
- Shahvelayati, Ashraf S.,Ghazvini, Maryam,Yadollahzadeh, Khadijeh,Delbari, Akram S.
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- Uncommon condensations of 1,2,3-triketone 2-oximes with o-phenylenediamine
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A condensation of 2-hydroxyimino-5,5-dimethylcyclohexane-1,3-dione, ninhydrin oxime and 3-hydroxyiminopentane-2,4-dione with o-phenylenediamine in the presence of CF3COOH provided 6,6-dimethyl-6,7-dihydroquinoxalino-[2,3-a]phenazine, benzimidazo[2′,1′:1,2]isoquino[3,4-b]quinoxaline, and 2-acetyl-3-methylquinoxaline oxime, respectively. An ability to form stacking dimers was found for the second product.
- Ukhin, Lev Yu.,Kuz'mina, Lyudmila G.,Alexeenko, Danil V.,Belousova, Lyudmila V.,Morkovnik, Anatolii S.,Borodkin, Gennadii S.,Gribanova, Tatyana N.
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