Abstract
The reactions of 4-aminobenzoic and 4-aminophenylacetic acids amides with maleic anhydride yielded the corresponding maleic acid monoamides, the cyclization of which gave 4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoic and 4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenylethanoic acids amides. Their reactions with secondary amines afforded the corresponding 4-(3-dialkylamino-2,5-dioxo-2,3,4,5-tetrahydro-1H-pyrrol-1-yl)benzoic and 4-(3-dialkylamino-2,5-dioxo-2,3,4,5-tetrahydro-1H-pyrrol-1-yl)phenylethanoic acids amides.
REFERENCES
Mikhailin, Yu.A., Termoustoychivye polimery i polimernye materialy (Heat-Resistant Polymers and Polymeric Materials), St. Petersburg: Professiya, 2006.
Mitrasov, Yu.N., Kolyamshin, O.A., and Danilov, V.A., Maleinimidy: sintez, svoistva i polimery na ikh osnove (Maleimides: Synthesis, Properties, and Polymers Based on Them), Cheboksary: Chuvash. Gos. Ped. Univ., 2017. 286 p.
Sava, M., Găină, C., and Găină, V., Rev. Roum. Chim., 2001, vol. 46, p. 1167.
Sava, M.J., Appl. Polym. Sci., 2004, vol. 91, p. 3806. https://doi.org/10.1002/app.13548
Patent US 3887582, 1975.
Alwin, K., Johan, B., and Theo, J.D., Polymer, 2010, vol. 51, p. 1887. https://doi.org/10.1016/j.polymer.2010.03.015
Patent US 5198551, 1993.
Milano, J.S., Mekkid, S., and Vernet, J.L., Eur. Polym. J., 1998, vol. 34, p. 717. https://doi.org/10.1016/S0014-3057(97)00184-5
Milano, J.С., Mekkid, S., and Vernet, J.L., Eur. Polym. J., 1997, vol. 33, p. 1333. https://doi.org/10.1016/S0014-3057(96)00143-7
Patel, J.R. and Dholakiya, B.Z., Med. Chem. Res., 2012, vol. 21, p. 1977. https://doi.org/10.1007/s00044-011-9718-x
Ol’shevskaya, V.A., Makarenkov, A.V., Korotkova, N.S., Kononova, E.G., Konovalova, N.V., and Kalinin, V.N., Doklady Chem., 2014, vol. 458, no. 1, p. 165. https://doi.org/10.1134/S0012500814090018
Patel, J.R., Dhorajiya, B.D., Dholakiya, B.Z., Badria, F.A., and Ibrahim, A.S., Med. Chem. Res., 2014, vol. 23, p. 3907. https://doi.org/10.1007/s00044-014-0965-5
Patel, J.R. and Dholakiya, B.Z., Res. Chem. Intermed., 2013, vol. 39, p. 4159. https://doi.org/10.1007/s11164-012-0932-z
Switzerland Patent 583226, 1976.
Japan Patent 30308, 1968.
Japan Patent 30313, 1968.
Japan Patent 21433, 1968.
Kolyamshin, O.A., Danilov, V.A., Dashkova, G.Yu., and Kol’tsov, N.I., Russ. J. Org. Chem., 2005, vol. 41, no. 11, p. 1657. https://doi.org/10.1007/s11178-006-0014-z
Kolyamshin, O.A., Danilov, V.A., and Kol’tsov, N.I., Russ. J. Org. Chem., 2007, vol. 43, no. 3, p. 393. https://doi.org/10.1134/S1070428007030104
Kolyamshin, O.A., Mitrasov, Yu.N., Danilov, V.A., and Avruiskaya, A.A., Russ. J. Gen. Chem., 2019, vol. 89, no. 9, p. 1740. https://doi.org/10.1134/S1070363219090020
Pretch, E., Bühlmann, P., and Affolter, C., Structure Determination of Organic Compounds: Tables of Spectral Data, Berlin: Springer, 2000.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Rights and permissions
About this article
Cite this article
Kolyamshin, O.A., Mitrasov, Y.N., Danilov, V.A. et al. Synthesis and Some Transformations of 4-(2,5-Dihydro-2,5-dioxo-1H-pyrrrol-1-yl)benzoic and -Phenylacetic Acids Amides. Russ J Gen Chem 93, 240–244 (2023). https://doi.org/10.1134/S1070363223020020
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363223020020