Ionic-liquid-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene — An efficient and recyclable organocatalyst for Michael addition to α,β-unsaturated ketones

2012 ◽  
Vol 90 (3) ◽  
pp. 290-297 ◽  
Author(s):  
Manoj Kumar Muthyala ◽  
Bhupender S Chhikara ◽  
Keykavous Parang ◽  
Anil Kumar
Keyword(s):  
Ionic Liquid ◽  
Michael Addition ◽  
Room Temperature ◽  
Significant Loss ◽  
Unsaturated Ketones ◽  
Ability To Act ◽  
Solvent Free Conditions ◽  
Active Methylene Compounds ◽  
Active Methylene ◽  
The Michael Addition

A novel ionic-liquid-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (IL–TBD) was synthesized and investigated for its ability to act as an active organocatalyst in the Michael addition of active methylene compounds and thiophenols to chalcones under solvent-free conditions. The IL–TBD afforded Michael addition products in excellent yields (82%–94%) at room temperature, and it was simply recycled and reused at least five times without significant loss of catalytic activity.

Potassium phosphate–ionic liquid mediated selective mono-Michael addition

2015 ◽  
Vol 39 (9) ◽  
pp. 6726-6729 ◽  
Author(s):  
Anand D. Sawant ◽  
Suryabala D. Jagadale ◽  
Uday V. Desai ◽  
Manikrao M. Salunkhe
Keyword(s):  
Ionic Liquid ◽  
Michael Addition ◽  
Room Temperature ◽  
Potassium Phosphate ◽  
Nmr Analysis ◽  
Active Methylene Compounds ◽  
Dosy Nmr ◽  
Active Methylene

A process for exclusive mono-Michael addition of active methylene compounds to conjugated esters, nitriles and ketones is developed. An ionic liquid-mediated reaction is carried out at room temperature. A reaction carried out at 60 °C resulted in a double-addition. A mechanism is proposed and supported by P31 and DOSY NMR analysis.

Preparation and Characterization of a Novel Room Temperature Dicationic Ionic Liquid and its Application in the Synthesis of Xanthenediones Under Solvent-Free Conditions

2018 ◽  
Vol 21 (8) ◽  
pp. 602-608 ◽  
Author(s):  
Zainab Ehsani-Nasab ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Room Temperature ◽  
Reaction Times ◽  
Significant Loss ◽  
Solvent Free ◽  
Acidity Function ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Hammett Acidity Function ◽  
Dicationic Ionic Liquid

Aim and Objective: In the present work, 1, 1’-sulfinyldiethylammonium bis (hydrogen sulfate) as a novel room temperature dicationic ionic liquid was synthesized and used as a catalyst for xanthenediones synthesis. Material and Method: The dicationic ionic liquid has been synthesized using ethylamine and thionyl chloride as precursors. Then, by the reaction of [(EtNH2)2SO]Cl2 with H2SO4, [(EtNH2)2SO][HSO4]2 was prepared and after that, it was characterized by FT-IR, 1H NMR, 13C NMR as well as Hammett acidity function. This dicationic ionic liquid was used as a catalyst for the synthesis of xanthenediones via condensation of structurally diverse aldehydes and dimedone under solvent-free conditions. The progress of the reaction was monitored by thin layer chromatography (ethyl acetate/n-hexane = 3/7). Results: An efficient solvent-free method for the synthesis of xanthenediones has been developed in the presence of [(EtNH2)2SO][HSO4]2 as a powerful catalyst with high to excellent yields, and short reaction times. Additionally, recycling studies have demonstrated that the dicationic ionic liquid can be readily recovered and reused at least four times without significant loss of its catalytic activity. Conclusion: This new dicationic ionic liquid can act as a highly efficient catalyst for xanthenediones synthesis under solvent-free conditions.

Task-specific ionic-liquid-catalyzed efficient synthesis of indole derivatives under solvent-free conditions

2010 ◽  
Vol 88 (2) ◽  
pp. 150-154 ◽  
Author(s):  
Sudarshan Das ◽  
Matiur Rahman ◽  
Dhiman Kundu ◽  
Adinath Majee ◽  
Alakananda Hajra
Keyword(s):  
Ionic Liquid ◽  
Room Temperature ◽  
Acid Catalyst ◽  
Significant Loss ◽  
Solvent Free ◽  
Indole Derivatives ◽  
Efficient Synthesis ◽  
Solvent Free Conditions ◽  
High Yields ◽  
Task Specific Ionic Liquid

A sulfonic-acid-functionalized ionic liquid is used as a Brønsted acid catalyst for the efficient synthesis of indole derivatives in good-to-high yields at room temperature under solvent-free conditions. The catalyst can be reused for ten consecutive runs without significant loss of activity.

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