One-pot synthesis of 3-carbomoyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid
- Authors: Fedoseev S.V1, Lipin K.V1, Ershov O.V1
-
Affiliations:
- I.N. Ul'yanov Chuvash State University
- Issue: Vol 59, No 3 (2023)
- Pages: 400-404
- Section: Articles
- URL: https://aspvestnik.ru/0514-7492/article/view/666369
- DOI: https://doi.org/10.31857/S0514749223030114
- EDN: https://elibrary.ru/TKTQEJ
- ID: 666369
Cite item
Abstract
A one-pot method for the synthesis of 3-carbomoyl-2-oxo-1,2-dihydropyridine-4-carboxylic acids has been developed, which consists in the interaction of 4-oxoalkane-1,1,2,2-tetracarbonitriles with water and the hydrolysis of the resulting mixture of 2-oxo-1, 2-dihydropyridine-3,4-dicarbonitrile and 2-oxo-4-cyano-1,2-dihydropyridine-3-carboxamide with sodium hydroxide solution.
About the authors
S. V Fedoseev
I.N. Ul'yanov Chuvash State University
Email: sergey.fedoseev88@gmail.com
K. V Lipin
I.N. Ul'yanov Chuvash State University
Email: sergey.fedoseev88@gmail.com
O. V Ershov
I.N. Ul'yanov Chuvash State University
Email: sergey.fedoseev88@gmail.com
References
- Crocetti L., Vergelli C., Guerrini G., Giovannoni M.P., Kirpotina L.N., Khlebnikov A.I., Ghelardini C., Di Cesare Mannelli L., Lucarini E., Schepetkin I.A., Quinn M.T. Molecules. 2021, 26, 6583. doi: 10.3390/molecules26216583
- Eastwood P., Gonzalez J., Paredes S., Fonquerna S., Card�s A., Alonso J.A., Nueda A., Domenech T., Reinoso R.F., Vidal B. Bioorg. Med. Chem. Lett. 2010, 20, 1634-1637. doi: 10.1016/j.bmcl.2010.01.077
- Fearon D., Westwood I.M., van Montfort R.L.M., Bayliss R., Jones K., Bavetsias V. Bioorg. Med. Chem. 2018, 26, 3021-3029. doi: 10.1016/j.bmc.2018.04.033
- Bryan M.C., Burdick D.J., Chan B.K., Chen Y., Clausen S., Dotson J., Eigenbrot C., Elliott R., Hanan E.J., Heald R., Jackson P., La H., Lainchbury M., Malek S., Mann S.E., Purkey H.E., Schaefer G., Schmidt S., Seward E., Sideris S., Wang S., Yen I., Yu C., Heffron T.P. ACS Med. Chem. Lett. 2016, 7, 100-104. doi: 10.1021/acsmedchemlett.5b00428
- Jian Y., Hulpia F., Risseeuw M.D.P., Forbes H.E., Munier-Lehmann H., Caljon G., Boshoff H.I.M., Van Calenbergh S. Eur. J. Med. Chem. 2020, 201, 112450. doi: 10.1016/j.ejmech.2020.112450
- El-Gohary N.S., Shaaban M.I. Arch. Pharm. 2015, 348, 666-680. doi: 10.1002/ardp.201500037
- Basu S., Middya S., Banerjee M., Ghosh R., Pryde D.C., Yadav D.B., Shrivastava R., Surya A. Eur. J. Med. Chem. 2022, 229, 114087. doi: 10.1016/j.ejmech.2021.114087
- Oza V., Ashwell S., Brassil P., Breed J., Ezhuthachan J., Deng C., Grondine M., Horn C., Liu D., Lyne P., Newcombe N., Pass M., Read J., Su M., Toader D., Yu D., Yu Y., Zabludoff S. Bioorg. Med. Chem. Lett. 2012, 22, 2330-2337. doi: 10.1016/j.bmcl.2012.01.043
- Chonan T., Tanaka H., Yamamoto D., Yashiro M., Oi T., Wakasugi D., Ohoka-Sugita A., Io F., Koretsune H., Hiratate A. Bioorg. Med. Chem. Lett. 2010, 20, 3965-3968. doi: 10.1016/j.bmcl.2010.04.134
- Dulla B., Wan B., Franzblau S.G., Kapavarapu R., Reiser O., Iqbal J., Pal M. Bioorg. Med. Chem. Lett. 2012, 22, 4629-4635. doi: 10.1016/j.bmcl.2012.05.096
- Howard N.I., Dias M.V.B., Peyrot F., Chen L., Schmidt M.F., Blundell T.L., Abell C. ChemMedChem. 2015, 10, 116-133. doi: 10.1002/cmdc.201402298
- Breda A., Machado P., Rosado L.A., Souto A.A., Santos D.S., Basso L.A. Eur. J. Med. Chem. 2012, 54, 113-122. doi: 10.1016/j.ejmech.2012.04.031
- Ershov O.V., Fedoseev S.V., Belikov M.Yu., Ievlev M.Yu. RSC Adv. 2015, 5, 34191-34198. doi: 10.1039/C5RA01642H
- Ershov O.V., Fedoseev S.V., Ievlev M.Yu., Belikov M.Yu. Dyes Pigm. 2016, 134, 459-464. doi: 10.1016/j.dyepig.2016.07.037
- Ershov O.V., Ievlev M.Y., Belikov M.Y., Fedoseev S.V. Tetrahedron Lett. 2018, 59, 2189-2192. doi: 10.1016/j.tetlet.2018.04.067
Supplementary files
