Microwave-promoted morita-baylis-hillman reactions: efficient synthesis of new monoacylglycerols (MAGs) as potential anti-parasitic compounds

• Autor(a) principal: Sousa,Suervy C. O
• Data de Publicação: 2011
• Outros Autores: Junior,Claudio G. L, Silva,Fábio P. L, Andrade,Natália G, Barbosa,Ticiano P, Vasconcellos,Mário L. A. A
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Journal of the Brazilian Chemical Society (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011000900003
• topic: Morita-Baylis-Hillman reaction; microwaves; monoacylglycerols; acrylates; potential antiparasitic

In this article we describe microwave irradiation promoting the synthesis of a hydrophilic monoacylglycerol, MAG, by hydrolysis of acrylate (15 min, 100%). After, MAG was transformed in hydrophilic Morita-Baylis-Hillman adducts (MBHA), (54-82%, pathway 1). In pathway 2, the different lipophilic MBHAs were prepared in high yields (90-100%) and transformed on hydrophilic MBHA, in 70-90%. Through the high temperature synthesis of one MBHA, a unprecedented indolizine formation was detected by GC-MS, . All results are in agreement with the new unified mechanism to the Morita-Baylis-Hillman reaction. These new monoacylglycerols, as well the its synthetic precursors, are new potential antiparasitic compounds.