Rational use of substituted N-allyl and N,N-diallylanilines in the stereoselective synthesis of novel 2-alkenyltetrahydro-1-benzazepines |
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| Authors: | Lina María Acosta Alí Bahsas |
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| Institution: | a Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander. A. A. 678, Bucaramanga, Colombia
b Laboratorio de RMN, Grupo de Productos Naturales. Departamento de Química, Universidad de los Andes, Mérida 5101, Venezuela |
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| Abstract: | Two new series of 1,4-epoxy-2-exo-vinyl(isopropenyl)tetrahydro-1-benzazepines and cis-2-vinyl(isopropenyl)-4-hydroxytetrahydro-1-benzazepines were prepared by an efficient three/four-step route from available substituted N,N-diallylanilines and mono N-allylanilines. The amino-Claisen rearrangement and the sequential oxidation/intramolecular 1,3-dipolar cycloaddition reactions were used as the key steps in this synthesis. All the synthesized compounds were fully characterized by IR, GC-MS and NMR techniques. |
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| Keywords: | 1 4-Epoxy-2-alkenyltetrahydro-1-benzazepines 2-Alkenyl-4-hydroxytetrahydro-1-benzazepines Intramolecular 1 3-dipolar cycloaddition ortho-Allylanilines N-Allylanilines |
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