- PII
- S30346304S0514749225050137-1
- DOI
- 10.7868/S3034630425050137
- Publication type
- Article
- Status
- Published
- Authors
- Volume/ Edition
- Volume 61 / Issue number 5
- Pages
- 614-620
- Abstract
- The methods for the synthesis of unsaturated ketones of the furan series based on the reaction of aldol-crotonic condensation of furfurol with some unsaturated ketones have been developed. It was found that among the used methods, the most optimal are the reactions in a medium of alcoholic solution of NaOH at room temperature, which pass more regioselectively with the formation of unsaturated ketones with high yields (65–75%), in this case the formation of side products is excluded. The availability of the synthesized unsaturated ketones of double bond and ketogroup in the molecule makes them perspective substrates in the synthesis of a number of various potentially biologically active compounds. In particular, it has been shown that the unsaturated ketones undergo the reaction with hydrazine-hydrate, thiosemicarbazide and secondary amines with the formation of the corresponding new furane derivatives.
- Keywords
- альдольно-кротоновая конденсация непредельные кетоны фурфурол пиразолин тиосемикарбазон гидразин гидрат
- Date of publication
- 17.12.2025
- Year of publication
- 2025
- Number of purchasers
- 0
- Views
- 44
References
- 1. Машковский М.Д. Лекарственные средства. М.: Новая волна, 2012, 1216.
- 2. Atta-Ur-Rahman. Bioactive Natural Products (Part E). Amsterdam–Lausanne–New York–Oxford–Shannon–Singapore–Tokyo: Elsevier. 2000, 24, 231.
- 3. Jiang X., Wang X., Huang X., Li G., Yu C. J. Saudi Chem. Soc. 2017, 21, 587–592. doi 10.1016/j.jscs.2017.01.004
- 4. Клочкова И.Н., Аниськов А.А.,Сазонов А.А., Воронов И.И., Французов А.А. Изв. Сарат. ун-та. Сер. хим. биол. экол. 2006, 6, 35.
- 5. Сердюк О.В., Чаликиди П.Н., Бутин А.В. ХГС. 2012, 9, 1376–1392. @@Serdyuk O.V., Chalikidi P.N., Butin A.V. Chem. Heterocycl. Compd. 2012, 48, 1281–1296. doi 10.1007/s10593-012-1135-7
- 6. Golovanov A., Odin I., Nebritova A.E. Russ. J. Org. Chem. 2014, 50, 943–947. doi 10.1134/S1070428014070045
- 7. Piutti C., Quartieri F. Molecules. 2013, 18, 12290–12312. doi 10.3390/molecules 181012290
- 8. Yadav G.D., Yadav A.R. RSC Advances. 2014, 4, 63772–63778. doi 10.1039/C4RA09194A
- 9. Kikhtyanin O., Kelbichová V., Vitvarová D., Kubu M., Kubicka D. Catalys is Today. 2014, 227, 154–162. doi 10.1016/j.cattod.2013.10.059
- 10. Kantlam Ch, Srinivasa Murthy M and Narsimha Reddy Y. J. Pharm. Res. 2015, 14, 90–93.
- 11. Голованов А.А., Бекин В.В., Злотский С.С., Кунавин Ю.А., Вологжанина А.В., Гусев Д.М., Бунев А.С. ХГС. 2015, 51, 929–932. @@Golovanov A.A. Bekin V.V., Zlotskii S.S., Kunavin Y.A., Vologzhanina A.V., Gusev D.M., Bunev A.S. Chem. Heterocycl. Compd. 2015, 51, 929–932. doi 10.1007/s10593-015-1799-x
- 12. Иовель И., Голомба Л., Попелис Ю., Гринберга С., Лукевиц Э. ХГС. 2000, 7, 890–897. @@Iovel I., Golomba L., Popelis Y., Grinberga S., Lukevics E. Chem. Heterocycl. Compd. 2000, 36, 779–786. doi 10.1007/BF02256909
- 13. González M.J., López L.A., Vicente R. Org. Lett. 2014, 16, 5780–5783. doi 10.1021/ol502848n
- 14. Palmer L.I. and de Alaniz J.R. Org. Lett. 2013, 15, 476–479. doi 10.1021/ol303263q
- 15. Неволина Т.А., Щербинина В.А., Шпунтова П.М., Бутин А.В. ХГС. 2012, 5, 888–890. @@Nevolina T.A., Shcherbinin V.A., Shpuntov P.M., Butin A.V. Chem. Heterocycl. Compd. 2012, 48, 828–830. doi 10.1007/s10593-012-1063-6