Abstract
The nucleophilic addition of n-butyl- and benzylamines to 1-(4-nitrophenyl)-5H-pyrrolin-5-one and 1-(4-sulfamoylphenyl)-5H-pyrrolin-2-one at 50°C in an excess of the amines with the formation of N-substituted amides of 3-alkyl(benzyl)amino-4-(4-R-anilino)butyric acids was investigated. The N-substituted amides of 3-arylamino-4-hydroxybutyric and 4-hydroxy-2-butenoic acids were synthesized from 2(5H)-furanone and aromatic amines (1:3) at 180°C. 4-Alkylamino-1-(4-nitrophenyl)pyrrolid-2-ones were obtained in the reaction of 1-(4-nitrophenyl)-5-pyrrolin-2-one with ammonia or aliphatic, alicyclic, and aromatic amines (1:3, 90°C, in DMF).
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
L. A. Badovskaya, Z. I. Tyukhteneva, and Yu. V. Naidenov, in: Chemistry for Medicine and Veterinary Science [in Russian], Sb. Nauch. Tr. Sarat. Gos. Un-ta, Saratov (1998), p. 7.
V. A. Sedavkina and N. A. Morozova, Khim. Geterotsikl. Soedin., 331 (1972).
A. A. Ponomarev and V. A. Sedavkina, Khim. Geterotsikl. Soedin., 809 (1969).
N. A. Morozova, V. A. Sedavkina, and A. Yu. Egorova, Khim. Geterotsikl. Soedin., 349 (1994).
V. A. Sedavkina, N. A. Morozova, and A. Yu. Egorova, in: Chemistry and Technology of Furan Compounds [in Russian], Sb. Nauch. Tr. Kuban. Gos. Tekhn. Un-ta, Krasnodar (1995), p. 21.
I. K. Kalnin' and E. Yu. Gudrinietse, Khim. Geterotsikl. Soedin., 867 (1972).
M. Semonsky, A. Cerny, B. Kakac, and V. Subrt, Coll. Czech. Chem. Commun., 28, 3278 (1963).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sibiryakova, M.A., Muzychenko, G.F., Burlaka, S.D. et al. Nucleophilic Addition of Amines to N-Aryl-substituted Pyrrolin-2-ones. Chemistry of Heterocyclic Compounds 38, 533–538 (2002). https://doi.org/10.1023/A:1019548826977
Issue Date:
DOI: https://doi.org/10.1023/A:1019548826977