Síntese/funcionalização visando a obtenção de organoselenilcumarinas: uma revisão da literatura

Abstract

Coumarins are a class of heterocyclic compounds commonly resulting from the reaction between pyrone and benzene. Coumarin was first synthesized in 1868 by Perkin, after being extracted from Tonka bean in 1820 by Vogel and Guibourt. Currently, more than 1000 coumarin derivatives are registered in the Cambridge Structural Database. This broad scope of structures is the result of diverse research, which has led to protocols for the synthesis and functionalization of new coumarins. Among the classical methodologies are those proposed by Pechmann, Perkin and Knoevenagel. Nowadays, several routes of synthesis and functionalization of coumarins can be found in the literature, however, coumarins containing a selenium atom in the structure is still something that has not been explored. Thus, the present work aimed to review the literature and describe the methodologies for obtaining selenylcoumarins, due to the importance of organoselenium compounds in organic chemistry. In all we found nine articles, published between the years 2014 and 2021, three of synthesis of 3-selenylcoumarins, four of functionalization of coumarins to obtain 3-selenylcoumarins and two of functionalization of coumarins to synthesize 4- selenylcoumarins. In general, the research shows consistent methodologies, leading to good yields. In addition, most of them follow Green Chemistry protocols. The biological/pharmacological properties of selenylcoumarins are not yet well established, however, it is already known that 4-selenylcoumarins present antioxidant and antiproliferative activity. We conclude that, by presenting an exploratory character, the obtention of selenylcoumarins still presents a lot of potentiality, as well as the studies that are in progress regarding their bioactivities.