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 Dedicated to the memory of Professor Luis Astudillo Saavedra for his scientific career, support and fraternity.

Pedro De-La-Torre, Edison Osorio, Jans H. Alzate-Morales, Julio Caballero, Jorge Trilleras, Luis Astudillo-Saavedra, Iván Brito, Alejandro Cárdenas, Jairo Quiroga, Margarita Gutiérrez

Resultado de la investigación: Contribución a una revistaArtículo

13 Citas (Scopus)

Resumen

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-yl) acetonitrile: 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-PTC 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⋯N intermolecular interactions (Ho⋯NC = 2.45 Å, Co⋯NC = 3.348(3) Å, Ho⋯ NC = 162°), forming centrosymmetric ring R22 (20) along the crystallographic a axis.

Idioma originalInglés
Páginas (desde-hasta)1666-1674
Número de páginas9
PublicaciónUltrasonics Sonochemistry
Volumen21
N.º5
DOI
EstadoPublicada - 1 ene 2014

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