Synthesis of piridil-acetilene through a coupling of sonogashira assisted by microwaves
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Abstract
The use of the microwave in organic synthesis to obtain pyridyl tolans has been bet, since it is capable of providing enough energy in such a way that it is possible to cross a certain energy barrier, its use provides a decrease in the reaction time resulting in high performance products in which it was possible to limit the purification processes. Thus, in the present work, the synthesis of palladium-catalyzed pyridyl-tolanes was carried out by means of a microwave-assisted Sonogashira coupling. The purification of the synthesized compounds was carried out by flash column chromatography using silica gel 60 GF254 with a positive pressure of nitrogen and with solvents suitable for the removal of undesirable inorganic matter (Cu residues). The characterization was made using Nuclear Magnetic Resonance of both Hydrogen and Carbon, in order to demonstrate the presence of the triple bond formed with the Sonogashira coupling. Nuclear Magnetic Resonance Spectra were recorded on a Bruker AMX-300 spectrophotometer equipped with a 5mm reverse multinuclear probe, using CDCl3 as the solvent. As a result, 2-pyridyl-tolane, 3-pyridyl-tolane and 4-pyridyl-tolane were obtained, which were synthesized with acceptable yields of 71, 73 and 78% respectively.
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