ARYLATION OF 3-(2-FURYL)-2-METHYLPROPENAL BY ARENEDIAZONIUM SALTS

A. Sitar, O. Skrypska, O. Lesyuk, O. Motovylsky, E. Bila, R. Lytvyn, Yu. Horak, M. Obushak


DOI: http://dx.doi.org/10.30970/vch.6401.249

Abstract


Arylfuran’s are an important class of compounds in practical terms. The availability and broad functionality of arylfuran derivatives open wide opportunities for obtaining a significant variety of potential biologically active substances. It is known that many biologically active compounds have been found based on arylfuran derivatives, moreover a number of drugs have been discovered. Functionalized furans, in particular aldehydes of the arylfuran series, are frequently used reagents in organic synthesis especially for creation of combinatorial libraries for screening on biological activity. Taking all these into account, it is obvious that the synthesis of new functionalized furan derivatives with simple practical procedure is an urgent task.

Herein we described the arylation of 3-(2-furyl)-2-methylpropenal with arenediazonium salts. It was established that 3-(2-furyl)-2-methylpropenal react with arenediazonium salts to form arylation products in position 5 of furan ring. Arylation was carried out in water-acetone medium in the presence of a catalyst – CuCl2. Thus reaction products are obtained with yields up to 49 %. Series of 3-(5-aryl-2-furyl) methylacrylaldehydes – reagents for the synthesis of condensed heterocycles contains arylfuran moiety were prepared. The best yields were obtained when dichloro-substituted arenediazonium salts were used in the arylation reaction while the lowest yields were obtained in case of mono substituted arenediazonium salts. The reaction yields are rather low, but the starting reagents are cheap and commercially available reagents. Moreover, the developed synthetic procedure is simple and the purification of the reaction products does not require the use of column chromatography. This circumstance makes it possible to scale up the synthesis of the desired 2-methyl-3-arylfurylacroleins to multigram quantities. The structure of the obtained compounds was reliably confirmed using 1H and 13C NMR spectroscopy. For all the prepared compounds, the most characteristic signals in the NMR spectra are the signals of the proton of the aldehyde group in the range of 9.5–9.6 ppm (1H NMR) and the position of the carbon of the aldehyde group at 193–194 ppm (13C NMR).

  

Keywords: furan derivatives, arylfurans, arylation, arenediazonium salts.


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