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Study of the Hydroamination Reaction of Methyl Acetylenedicarboxylate with Aromatic Amines and its Heterocyclization Products
Author(s) -
Sol Shmidt Maria,
Florencia Martini Maria,
Oppezzo Guido A.,
Mercedes Blanco Maria,
Moglioni Albertina G.
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202003023
Subject(s) - hydroamination , diphenylamine , dimethyl acetylenedicarboxylate , aniline , chemistry , acetic acid , organic chemistry , medicinal chemistry , acetylenedicarboxylate , enamine , catalysis , cycloaddition
Here we describe the reaction of dimethyl acetylenedicarboxylate 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 characteristics 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.