Lina M. Acosta Quintero, A. Palma, M. Nogueras
Nov 8, 2012
Citations
0
Influential Citations
10
Citations
Journal
Synthesis
Abstract
New series of polyfunctionalized 2,3,4,5-tetrahydro-1,4-epoxy-1-benzazepines and 2,3,4,5-tetrahydro-1 H -1-benzazepin-4-ols substituted at C2 with 2-methylprop-1-enyl, ( E )-styryl, and ( E )-pent-1-enyl were synthesized starting from the corresponding N -alkenyl-substituted [prenyl, trans -cinnamyl, ( E )-hex-2-enyl] 2-allylanilines by a three-step sequence consisting of selective oxidation of aromatic secondary amines, intramolecular nitrone–olefin 1,3-dipolar cycloaddition, and reductive cleavage. The intramolecular 1,3-dipolar cycloaddition is stereoselective favoring the exo -cycloadducts (ratio exo / endo 2–3:1). The stereochemistry was determined by exhaustive NMR analysis and X-ray diffraction.