Ultrasound-assisted phase-transfer catalysis method in an aqueous medium to promote the Knoevenagel reaction: Advantages over the conventional and microwave-assisted solvent-free/catalyst-free method

dc.creatorDe-La-Torre, P.
dc.creatorOsorio, E.
dc.creatorAlzate-Morales, JH.
dc.creatorCaballero, J.
dc.creatorTrilleras, J.
dc.creatorAstudillo-Saavedra, L.
dc.creatorBrito, I.
dc.creatorCardenas, A.
dc.creatorQuiroga, J.
dc.creatorGutierrez, M.
dc.date2014-12-16T20:46:25Z
dc.date2014-12-16T20:46:25Z
dc.date2014-09
dc.date.accessioned2017-03-07T15:01:59Z
dc.date.available2017-03-07T15:01:59Z
dc.identifierULTRASONICS SONOCHEMISTRY 21 (5) : 1666-1674
dc.identifier1873-2828
dc.identifierhttp://dspace.utalca.cl/handle/1950/10150
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/377063
dc.descriptionUniv Talca, Inst Chem Nat Resources, Organ Synth Lab & Biol Activ LSO Act Bio, Talca, Chile; De-La-Torre, P (De-La-Torre, Pedro). Univ Talca, Ctr Bioinformat & Mol Simulat, Talca, Chile; Osorio, E (Osorio, Edison) ; Alzate-Morales, JH (Alzate-Morales, Jans H.) ; Caballero, J (Caballero, Julio).
dc.descriptionGiven the broad spectrum of uses of acrylonitrile derivatives as fluorescent probes, AChE inhibitors, and others, it is necessary to find easy, efficient and simple methods to synthesize and diversify these compounds. We report the results of a comparative study of the effects of three techniques on the reactions between heterocyclic aldehydes and 2-(benzo[d]thiazol-2-ypacetonitrile: stirring; ultrasound coupled to PTC conditions (US-PTC); and MW irradiation (MWI) under solvent and catalyst-free conditions. The effects of conditions on reaction parameters were evaluated and compared in terms of reaction time, yield, purity and outcomes. The US-FTC method is more efficient than the MWI and conventional methods. The reaction times were considerably shorter, with high yields (>90%) and good levels of purity. In addition, X-ray diffraction analysis and quantum mechanical calculations, at the level of density functional theory (DFT), ratify obtaining acrylonitrile isomers with E configurations. The crystal structure of 3c is stabilized by weak C-H-o center dot center dot center dot N intermolecular interactions (H-o center dot center dot center dot NC = 2.45 angstrom, C-o center dot center dot center dot NC = 3.348(3) angstrom, H-o center dot center dot center dot NC = 162 degrees), forming centrosymmetric ring R-2(2) (20) along the crystallographic a axis. (C) 2014 Elsevier B.V. All rights reserved.
dc.languageen
dc.publisherELSEVIER SCIENCE BV
dc.subjectPhase-transfer catalysis
dc.subjectX-ray crystallography
dc.subjectDensity functional theory
dc.subjectKnoevenagel reactions
dc.subjectUltrasound
dc.subjectMicrowave
dc.titleUltrasound-assisted phase-transfer catalysis method in an aqueous medium to promote the Knoevenagel reaction: Advantages over the conventional and microwave-assisted solvent-free/catalyst-free method
dc.typeArtículos de revistas


Este ítem pertenece a la siguiente institución