Yb(OTf)3-Catalyzed Bromination Reactions of Natural Product-like N-Benzyl Cinnamamides: A Facile Route to Diverse N-Substituted Amides of Pharmacological Interest

Diverse natural product-like N-benzyl cinnamamides were prepared by condensation of trans-cinnamic acid with substituted benzylamines in the presence of boric acid as catalyst. The further evaluation of this amides as a substrates of the bromo-arylation reaction, in the presence of N-bromosuccinimide (NBS) as the halogen source and under the catalysis of Yb(OTf)3, generate a different types of N-substituted amides: N-aryl 2,3-dibromopropanamides, N-(2-bromobenzyl) cinnamamides and tetrahydro-2-benzazepin-3-one as a new molecules. Here we discuss the formation of these main products on the basis of the electronic nature of the substituents present in the N-benzyl aromatic ring of the prepared cinnamamides.

• Fecha de publicación: 2013
• Institución: Ministerio de Ciencia Tecnología e Innovación
• Repositorio: Repositorio Institucional de Minciencias
• Idioma: eng
• OAI Identifier: oai:repositorio.minciencias.gov.co:20.500.14143/34189
• Acceso en línea: http://repositorio.colciencias.gov.co/handle/11146/34189
• Palabra clave: Biología vegetal; Productos farmacéuticos; Plantas medicinales; N-Aryl 2,3-dibromopropanamides; N-Benzyl cinnamamides; Boric acid; N-(2-Bromobenzyl) cinnamamides; Tetrahydro-2- benzazepin-3-ones; Yb(OTf)3-Catalyzed bromination reactions; Tecnología química; Bioquímica vegetal; Biomasa; Aceites esenciales
• License: http://purl.org/coar/access_right/c_f1cf