- PII
- S3034630425070162-1
- DOI
- 10.7868/S3034630425070162
- Publication type
- Article
- Status
- Published
- Authors
- Volume/ Edition
- Volume 61 / Issue number 7
- Pages
- 951-958
- Abstract
- A novel method for quinoline synthesis based on the interaction of propargylic alcohols with anilines in the presence of polyphosphoric acid (PPA) has been developed. It has been discovered that propargylic alcohols in a PPA medium are capable of hydrolysing into chalcones. The use of PPA in ethyl acetate solution has been demonstrated for the first time.
- Keywords
- ацетилены реакция Кучерова реакция Фриделя-Крафтса хинолины гетероциклизация пропаргиловые спирты
- Date of publication
- 01.07.2025
- Year of publication
- 2025
- Number of purchasers
- 0
- Views
- 21
References
- 1. Pentsak E.O., Murga M.S., Ananikov V.P. ACS Earth Space Chem., 2024, 8, 798–856. https://doi.org/10.1021/acsearthspacechem.3c00223
- 2. Schmidt E.Y., Trofimov B.A. Dokl. Chem., 2022, 505, 127–145. https://doi.org/10.1134/S0012500822700069
- 3. Danilkina N.A., Vasileva A.A., Balova I.A. Russ. Chem. Rev., 2020, 89, 125–171. https://doi.org/10.1070/RCR4902
- 4. Sindhua K.S., Anilkumar G. RSC Adv., 2014, 4, 27867–27887. https://doi.org/10.1039/C4RA02416H
- 5. Sindhu K.S., Thankachan A.P., Sajitha P.S., Anilkumar G. Org. Biomol. Chem., 2014, 13, 6891–6905. https://doi.org/10.1039/C5OB00697J
- 6. Rulev A.Yu., Ponomarev D.A. Angew. Chem. Int. Ed., 2019, 58, 7914. https://doi.org/10.1002/anie.201813398
- 7. Shabalin D.A. Russ. J. Org. Chem., 2023, 59, 1645–1659. https://doi.org/10.1134/S1070428023100019
- 8. Hein C.D., Liu X.-M., Wang D. Pharm. Res., 2008, 29, 2216–2230. https://doi.org/10.1007/s11095-008-9616-1
- 9. Sahharova L.T., Gordeev E.G., Eremin D.B., Ananikov V.P. ACS Catal., 2020, 10, 9872–9888. https://doi.org/10.1021/acscatal.0c02053
- 10. Orlov N.V., Chistyakov I.V., Khemchyan L.L., Ananikov V.P., Beletskaya I.P., Starikova Z.A. J. Org. Chem., 2014, 79, 12111–12121. https://doi.org/10.1021/jo501953f
- 11. Ananikov V.P., Khemchyan L.L., Beletskaya I.P., Starikova Z.A. Adv. Synth. Catal., 2010, 352, 2979–2992. https://doi.org/10.1002/adsc.201000606
- 12. Ananikov V.P., Beletskaya I.P. Pure Appl. Chem., 2007, 79, 1041–1056. https://doi.org/1041-1056
- 13. Voronin V.V., Ledovskaya M.S., Bogachenkov A.S., Rodygin K.S., Ananikov V.P. Molecules, 2018, 23, 2442. https://doi.org/10.3390/molecules23102442
- 14. Rodygin K.S., Ananikov V.P. Green Chem., 2016, 18, 482–486. https://doi.org/10.1039/c5gc01552a
- 15. Li X., Sun F., Shi H., Zhang B., He J., Wu J., Du Y. Org. Lett., 2023, 25, 3517–3521. https://doi.org/10.1021/acs.orglett.3c01095
- 16. Charushin V.N., Verbitskiy E.V., Chupakhin O.N., Vorobyev D.V., Gribanov P.S., Osipov S.N., Ivanov A.V., Martynovskaya S.V., Sagitova E.F., Dyachenko V.D., Krivokolysko S.G., Dotsenko V.V., Aksenov A.V., Aksenov D.A., Aksenov N.A., Larin A.A., Fershtat L.L., Muzalevskiy V.M., Nenajdenko V.G., Gulevskaya A.V., Pozharskii A.F., Filatova E.A., Belyaeva K.V., Trofimov B.A., Balova I.A., Danilkina N.A., Govdi A.I., Tikhomirov A.S., Shchekotikhin A.E., Novikov M.S., Rostovskii N.V., Khlebnikov A.F., Klimochkin Yu.N., Leonova M.V., Tkachenko I.M., Mamedov V.A., Mamedova V.L., Zhukova N.A., Semenov V.E., Sinyashin O.G., Borshchev O.V., Luponosov Yu.N., Ponomarenko S.A., Fisyuk A.S., Kostyuchenko A.S., Ilkin V.G., Beryozkina T.V., Bakulev V.A., Gazizov A.S., Zagidullin A.A., Karasik A.A., Kukushkin M.E., Beloglazkina E.K., Golantsov N.E., Festa A.A., Voskresensky L.G., Moshkin V.S., Buev E.M., Sosnovskikh V.Ya., Mironova I.A., Postnikov P.S., Zhdankin V.V., Yusubov M.S., Yaremenko I.A., Vil’ V.A., Krylov I.B., Terent’ev A.O., Gorbunova Yu.G., Martynov A.G., Tsivadze A.Yu., Stuzhin P.A., Ivanova S.S., Koifman O.I., Burov O.N., Kletskii M.E., Kurbatov S.V., Yarovaya O.I., Volcho K.P., Salakhutdinov N.F., Panova M.A., Burgart Ya.V., Saloutin V.I., Sitdikova A.R., Shchegravina E.S., Fedorov A.Yu. Russ. Chem. Rev., 2024, 93, RCR5125. https://doi.org/10.59761/RCR5125
- 17. Stoikov I.I., Antipin I.S., Burilov V.A., Kurbangalieva A.R., Rostovskii N.V., Pankova A.S., Balova I.A., Remizov Yu.O., Pevzner L.M., Petrov M.L., Vasilyev A.V., Averin A.D., Beletskaya I.P., Nenajdenko V.G., Beloglazkina E.K., Gromov S.P., Karlov S.S., Magdesieva T.V., Prishchenko A.A., Popkov S.V., Terent’ev A.O., Tsaplin G.V., Kustova T.P., Kochetova L.B., Magdalinova N.A., Krasnokutskaya E.A., Nyuchev A.V., Kuznetsova Yu.L., Fedorov A.Yu., Egorova A.Yu., Grinev V.S., Sorokin V.V., Ovchinnikov K.L., Kofanov E.R., Kolobov A.V., Rusinov V.L., Zyryanov G.V., Nosov E.V., Bakulev V.A., Belskaya N.P., Berezkina T.V., Obydennov D.L., Sosnovskikh V.Ya., Bakhtin S.G., Baranova O.V., Doroshkevich V.S., Raskildina G.Z., Sultanova R.M., Zlotskii S.S., Dyachenko V.D., Dyachenko I.V., Fisyuk A.S., Konshin V.V., Dotsenko V.V., Ivleva E.A., Reznikov A.N., Klimochkin Yu.N., Aksenov D.A., Aksenov N.A., Aksenov A.V., Burmistrov V.V., Butov G.M., Novakov I.A., Shikhaliev Kh.S., Stolpovskaya N.V., Medvedev S.M., Kandalintseva N.V., Prosenko O.I., Menshchikova E.B., Golovanov A.A., Khashirova S.Yu. Russ. J. Org. Chem., 2024, 60, 1361. https://doi.org/10.1134/S1070428024080013
- 18. Aksenov A.V., Makieva D.C., Arestov R.A., Arutiunov N.A., Aksenov D.A., Aksenov N.A., Leontiev A.V., Aksenova I.V. Int. J. Mol. Sci., 2024, 25, 8750. https://doi.org/10.3390/ijms25168750
- 19. Justaud F., Hachem A., Grée R. Eur. J. Org. Chem., 2021, 2021, 514–542. https://doi.org/10.1002/ejoc.202001494
- 20. Huhti A.-L., Gartaganis P.A. Can. J. Chem., 1956, 34, 785–797. https://doi.org/10.1139/v56-102
- 21. Levashov A.S., Aksenov N.A., Aksenova I.V., Konshin V.V. New J. Chem., 2017, 41, 8297–8304. https://doi.org/10.1039/C7NJ01376K
- 22. Ye J.L., Zhu Y.N., Geng H., Huang P.Q. Sci. China Chem., 2018, 61, 687–694. https://doi.org/10.1007/s11426-017-9160-1
- 23. Cheng D., Yan X., Shen J., Pu Y., Xu X., Yan J. Synthesis, 2020, 52, 1833–1840. https://doi.org/10.1055/s-0039-1691740
- 24. Rehan M., Hazra G., Ghorai P. Org. Lett., 2015, 17, 1668–1671. https://doi.org/10.1021/acs.orglett.5b00419