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Please use this identifier to cite or link to this item: http://dspace.utalca.cl/handle/1950/10150

Title: 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
Authors: De-La-Torre, P.
Osorio, E.
Alzate-Morales, JH.
Caballero, J.
Trilleras, J.
Astudillo-Saavedra, L.
Brito, I.
Cardenas, A.
Quiroga, J.
Gutierrez, M.
Keywords: Phase-transfer catalysis
X-ray crystallography
Density functional theory
Knoevenagel reactions
Issue Date: Sep-2014
Citation: ULTRASONICS SONOCHEMISTRY 21 (5) : 1666-1674
Abstract: Given 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.
Description: Univ 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).
URI: http://dspace.utalca.cl/handle/1950/10150
ISSN: 1873-2828
Appears in Collections:Artículos en publicaciones ISI - Universidad de Talca

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