No abstract

: A simple and efficient methodology for Friedel-Crafts acylation of 3-methylindole using Amberlyst 15 resin as catalyst is described. This methodology shows good selectivity towards formation of the products of 2-acylation, (3-methyl-1H-indol-2-yl)ketones. Several advantages can be ascribing to Amberlys-15, among them; it is ease of handling, quickly separable from the reaction mixture and does not produce chemical residues that must be eliminated. Besides, the catalyst can be easily recycled and reused with a minimal loss in activity through 6 reaction cycles. The catalyst was characterized by FT-IR spectroscopy and superficial acidity.

Herein we present an efficient method to synthesize novel complex ureas from simple ureas, with potential pharmacological activity. First, 3-methylindole ketones are protected via a two-phase N-tosylation reaction catalyzed by NBu 4 HSO 4 as the PTC. Second, an NBS bromination of the terminal methyl group is performed with high selectivity and very good yields. Finally, complex novel and promising ureas are synthesized in 46 %-92 % yields using non-base-catalyzed substitution reactions with simple monosubstituted and disubstituted ureas. All products were easily purified through column chromatography and/or crystallization. The overall procedure produces very high yields and selectivity for bromination.

En el trabajo se sintetizó nuevos compuestos heterocíclicos derivados del indol, de importancia biológica y con potencial actividad farmacológica, planteando una ruta sintética diferente a la que se utiliza en la obtención de compuestos similares. Se emplearon catalizadores heterogéneos en algunas etapas de síntesis, como alternativa eco-compatible.En ese punto se evaluó la eficacia, eficiencia y reutilización de catalizadores heterogéneos en obtención de cetonas derivadas de 3-metilindol mediante acilación de Friedel Crafts.Otros de los puntos del trabajo fueron: la obtención de nuevos compuestos bromados, a partir de 3-metil-1H-indolilcetonas, de gran importancia como intermediarios sintéticos. La obtención de nuevas ureas heterocíclicas derivadas de indol con potencial actividad farmacológica.Y el análisis estructural de los nuevos compuestos obtenidos mediante 1H-RMN y 13C-RMN.