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Abstract
Objectives: To prepare new indolic molecules and characterize them by spectroscopic methods. Materials and methods: All reagents were purchased from Aldrich, commercial grade. The purity of the products and the composition of the reaction mixtures were monitored by thin layer chromatography over Silufol UV254 0.25 mm-thick chromatoplates. Product isolation and purification were performed by column chromatography (SiO2), using ethyl acetate-petroleum ether mixtures as eluents. Results: The synthesis of new N-aryl-N-(3-indolmethyl) acetamides based on first step iminization reaction of indol-3-carbaldehyde is accomplished. The structures of the C-3 substituted indoles were confirmed by 1H-nmr and 13C-nmr studies supported by inverse-detected 2D NMR experiments and also through monocrystal X-ray diffraction. Conclusions: An efficient, economic, and fast synthetic route was designed to the construction of the N-aryl-N-(3-indolmethyl) acetamides, structural analogues of some alkaloids.
Key words: indole, acetamides, iminization
Resumen
Preparación sencilla de nuevas N-aril-N-(3-indolmetil) acetamidas y su análisis espectroscópico. Objetivos: Preparar nuevas moléculas indólicas y caracterizarlas por los métodos espectroscópicos. Materiales y métodos: Todos los reactivos fueron adquiridos de Aldrich, de grado comercial. La pureza de los productos y composición de las mezclas de reacción fueron monitoreadas por la cromatografía en capa delgada, Silufol UV254 0.25 mm-grosor de cromatoplacas. El aislamiento y purificación de los productos fueron realizados por la cromatografía en columna (SiO2), usando mezclas de acetato de etilo y éter de petróleo como eluentes. Resultados: Se ha realizado la síntesis de nuevas N-aril-N-(3-indolmetil) acetamidas, basada en la reacción de iminización del indol-3-carbaldehído. Las estructuras de los indoles C-3 sustituidos fueron confirmadas por estudios de 1H, 13C -RmN, experimentos de 2D RMN y también por difracción monocristal de Rayos X. Conclusiones: Se ha diseñado una nueva ruta de síntesis eficiente, económica y rápida para la construcción de las N-aril-N-(3-indolmetil) acetamidas, análogos estructurales de diversos alcaloides.
Palabras clave: indol, acetamidas, iminización
Resumo
Preparação simples de novas N-aril-N-(3-indolmetil)acetamidas e sua análise espectroscópica. Objetivos: Preparar novas moléculas indólicas e caracterizar-las através de métodos espectroscópicos. Materiais e métodos: Todos os reagentes foram obtidos de Aldrich, de tipo comercial. A pureza dos produtos e a composição das misturas de reação foram monitoradas por cromatografia em camada fina, Silufol UV254 0,25 mm de espessura das cromatoplacas. O isolamento e a purificação dos produtos foram feitos através de cromatografia em coluna (SiO2), utilizando misturas de acetato de etila e éter de petróleo como eluente. Resultados: Realizou-se a síntese de novas N-aril-N-(3-indolmetil)acetamidas, baseada na reação de iminización do indol-3-carbaldeído,. As estruturas dos indóis C-3 substituídos foram confirmadas por estudos de 1H, 13C -RMN, experimentos de 2D RMN e também por difração monocristal dos Rayos X. Conclusões: Desenhou-se una nova rota de síntese eficiente, econômica e rápida para a construção das N-aril-N-(3-indolmetil) acetamidas, análogos estruturais de vários alcalóides.
Palavras-chave: indol, acetamidas, iminização
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