Síntese promovida por irradiação de micro-ondas de novos adutos de Morita-Baylis-Hillman hidrossolúveis com potencial atividade antiparasitária : um propostapara o uso do glicerol

• Ano de defesa: 2011
• Autor(a) principal: Sousa, Suervy Canuto de Oliveira
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal da Paraí­ba; BR; Química; Programa de Pós-Graduação em Química; UFPB
• Palavras-chave em Português: Adutos de Morita-Baylis-Hillman; Irradiação de Microondas; Gliceroquímica; Monoacilglicerol (MAG) e Química Verde; Morita-Baylis-Hillman adducts; Microwave Irradiation; Glycerochemistry; Monoacylglycerols (MAG) and Green Chemistry; CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: https://repositorio.ufpb.br/jspui/handle/tede/7032

This study was conducted in order to develop the synthesis of new Morita-Baylis-Hillman adducts of (MBHA) water soluble (29-34) with potential parasitic activity, using glycerol (1) as raw material. Two synthetic routes were carried out producing twelve new MBHA (23 - 34), six of which have hydrophilic characteristics 29-34 (main target of the work) and six more hydrophobic 23 28 (as synthesis intermediates), and these intermediaries are also important for comparative studies of structure and biological activity (SAR). Starting from glycerol (1), we synthesize the 2,2-dimethyl-1,3-dioxolan-4-yl)methyl acrylates (21, 94%) and from this, two synthetic routes were investigated to produce the 29- 34 adducts. On Route 1, the adducts 29-34 were produced in one-step (54 - 82%) from the Michael acceptor 2,3-dihydroxypropyl acrylate 22, which was prepared in 100% yield from 21. In route 2, MBHA intermediates 23 - 28 were prepared directly from 21 (90 - 100%) and these adducts were subsequently processed in adducts 29-34 (70 - 90%). In the synthesis of adduct 32 was observed the formation of the Michael addition product 47 and Indolizines unprecedented 48 as co-products of synthesis and characterized only by CGMS during the synthetic route 2. All syntheses in this work were developed in industry standards convenient. The activation reaction by microwave irradiation (MW) was widely used in most steps of this synthetic work, leading to high chemical yields and reduced reaction times.