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A Phosphine-mediated Synthesis of 2,3,4,5-tetra-substituted Nhydroxypyrroles from α-oximino Ketones and Dialkyl Acetylenedicarboxylates Under Ionic Liquid Green-media

[ Vol. 21 , Issue. 1 ]

Author(s):

Ashraf S. Shahvelayati*, Maryam Ghazvini, Khadijeh Yadollahzadeh and Akram S. Delbari   Pages 14 - 18 ( 5 )

Abstract:


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.

Keywords:

Dialkyl acetylenedicarboxylate, α-oximinoketone, N-hydroxypyrroles, ionic liquid, tandem reaction, β-dicarbonyl compounds, green media, phosphine-mediated synthesis.

Affiliation:

Department of Chemistry, Yadegar-e-Imam Khomeini (RAH) Shahre-rey Branch, Islamic Azad University, Tehran, Department of Chemistry, Payame Noor University, P.O. Box, 19395-4697, Tehran, Department of Chemistry, Aliabad Katoul Branch, Islamic Azad University, Aliabad Katoul, Department of Chemistry, College of Science, Islamshahr Branch, Islamic Azad University, Islamshahr



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