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

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 MBHA...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2011-09, Vol.22 (9), p.1634-1643
Main Authors: Sousa, Suervy C. O., Junior, Claudio G. L., Silva, Fábio P. L., Andrade, Natália G., Barbosa, Ticiano P., Vasconcellos, Mário L. A. A.
Format: Article
Language:English
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
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Summary: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.
ISSN:0103-5053
1678-4790
DOI:10.1590/S0103-50532011000900003