Biginelli reaction catalyzed by copper nanoparticles.
We recently reported a novel synthesis of copper nanoparticles from copper sulphate utilizing the charge-compensatory effect of ionic liquid [bmim]BF(4) and ethylene glycol. The nanoparticles were characterized and found to be stable for one year. Here we hypothesize that the stabilized nanoparticles should be able to catalyze one-pot multicomponent organic reactions. We show that the nanoparticles catalyzed Biginelli reaction at room temperature to give the product 3,4-dihydopyrimidinone (>90% yield in ~15 minutes) from aldehydes, β-diketoester (ethylacetoacetate) and urea (or thiourea). ). Remarkably, such high yields and rapid kinetics was found to be independent of the electronic density on the reactant aryl-aldehyde. This was probably because even the surface-active particles reacted faster in the presence of ionic liquid as compared to conventional methods. The heterocyclic dihydropyrimidinones (DHPMs) and their derivatives are widely used in natural and synthetic organic chemistry due to their wide spectrum of biological and therapeutic properties (resulting from their antibacterial, antiviral, antitumor and anti-inflammatory activities. Our method has an easy work-up procedure and the nanoparticles could be recycled with minimal loss of efficiency.
Department of Chemistry, University of Delhi, Delhi, India.
Manika
M
Dewan
Ajeet
A
Kumar
Amit
A
Saxena
Arnab
A
De
Subho
S
Mozumdar
D000090:Acetoacetates / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007700:Kinetics; D053768:Metal Nanoparticles / Q000737:chemistry* / Q000648:ultrastructure; D046529:Microscopy, Electron, Transmission; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry; D014508:Urea / Q000737:chemistry; D014961:X-Ray Diffraction
D000090:Acetoacetates; D000447:Aldehydes; D011744:Pyrimidinones; D003300:Copper; D014508:Urea