A síntese via Adutos de Morita Baylis Hillman dos derivados 2-Indolizina em micro-ondas: novos potenciais moduladores de canais iônicos

• Ano de defesa: 2013
• Autor(a) principal: Cunha, Saraghina Maria Donato da
• 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; Derivados da 2-Indolizina; Microondas; Potenciais moduladores de canais iônicos; Programa quimioinformático Molinspitation; Morita-Baylis-Hillman adducts; 2 Indolizine Derivatives; Microwave; Potential Ion channel modulators; Molinspiration Cheminformatic program; CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: https://repositorio.ufpb.br/jspui/handle/tede/7104

This work presents microwave irradiation promoting synthetic studies that producing by the first time indolizine-2-carbonitrile (1) and indolizine-2-carboxylate (2) in good to high yields (70% and 81%, respectively) in one step from Morita-Baylis- Hillman adducts (MBHA) 2-(hydroxy(pyridin-2-yl)methyl)acrylonitrile (10) and methyl 2-(hydroxy(pyridin-2-yl)methyl)acrylate (9) respectively. These compounds were subsequently transformed in excellent yields on three 2-indolizine derivatives know in the literature. they are: indolizin-2-yl methanamine (5), 99%, indolizin-2-ylmethanol (6), 100%, indolizine-2-carboxylic acid (3), 100%, in new more three Indolizine, namely : tert-butyl (indolizin-2-ylmethyl) carbonate (7), 99% new, butyl-indolizine-2- carboxylate(4), 94% new, tert-butyl (indolizin-2-ylmethyl)carbamate (8), 86% new. All of the adducts were characterized by infrared physical methods, Gas Chromatography coupled to Mass Spectrometry and Nuclear Magnetic Resonance (1 H NMR and 13 C NMR).All syntheses were developed in this study appropriate industry standards. The reaction activation by microwave irradiation (MO) has been widely used in most synthetic stages of this work, leading to high chemical yields and reduced reaction times. The eight synthesized compounds were in silico designed aiming to present potential selective activities as modulators of ion channels. These activities were suggested by the high score values obtained by using Molinspiration cheminformatics program.