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

MARTINI, MARÍA FLORENCIA ; MOGLIONI, ALBERTINA G.; OPPEZZO, GUIDO A.; SHMIDT; MARÍA SOL; BLANCO, MARÍA MERCEDES

ChemistrySelect

John Wiley and Sons Inc

Año: 2021 vol. 6 p. 1969 - 1975

2365-6549

Here we describe the reaction of dimethyl acetylenedicarboxylatewith aniline, N-ethylaniline or diphenylamine. Thediasteromeric enamines obtained in each case are inequivocallycharacterized by 1H- and 13C-NMR spectra and computationalmethods. The heterocyclization reaction of each isolateddiasteromeric enamines, leads to different products dependingon the reaction conditions and the stereoelectronic characteristicsof the substrate. Thus, we were able to obtain 1-phenyl-2-methoxycarbonyl-4-quinolinone, and to find a new route forobtaining 1-phenyl-3-oxo-1,3-dihydro-2-indoliliden-acetic acidderivatives.