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-bromosuccinimid...

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Autores:
Tipo de recurso:
Fecha de publicación:
2013
Institución:
Ministerio de Ciencia, Tecnología e Innovación
Repositorio:
Repositorio 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
Rights
License
http://purl.org/coar/access_right/c_f1cf
Description
Summary: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.