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Note | Regular issue | Vol 45, No. 10, 1997, pp.2023-2031
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7888
Preparation of Enamines from the Condensation of Glycine Esters with Nitro-Heterocyclic Aldehydes

Hugo Cerecetto, Rossanna Di Maio, Mercedes González, and Gustavo Seoane*

*Cátedra de Química Orgánica, Facultad de Química, Universidad de la República, Avda. General Flores 2124, Casilla de Correo 1157, C. P. 1180 Montevideo, Uruguay


In order to prepare the imine derived from condensation of glycine ethyl ester and 5-nitrothiopene-2-carboxaldehyde, another compound was obtained instead. This product was the enamine, ethyl 2-amino-3-(5-nitro-2-thienyl)-2-propenoate, resulting from the condensation between the methylene of the glycine derivative and the heterocyclic carbonyl group. The reactivity of related amines and heterocyclic aldehydes was studied in order to get more insight about the mechanism of enamine formation. It was found that the nitro-heterocyclic group and the easy of enolization of the aminoacidic ester played an important role.