Study of the Hydroamination Reaction of Methyl Acetylenedicarboxylate with Aromatic Amines and its Heterocyclization Products

摘要

Here we describe the reaction of dimethyl acetylenedicarbox- ylate with aniline, N-ethylaniline or diphenylamine. The diasteromeric enamines obtained in each case are inequivocally characterized by 1 H- and 13 C-NMR spectra and computational methods. The heterocyclization reaction of each isolated diasteromeric enamines, leads to different products depending on the reaction conditions and the stereoelectronic character- istics of the substrate. Thus, we were able to obtain 1-phenyl-2- methoxycarbonyl-4-quinolinone, and to find a new route for obtaining 1-phenyl-3-oxo-1,3-dihydro-2-indoliliden-acetic acid derivatives.