Synthesis of 2,4-Disubstituted Quinolines by the Reaction of Propargylic Alcohols with Anilines in a Polyphosphoric Acid Medium

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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.

About the authors

A. V. Aksenov

North Caucasus Federal University

Email: aaksenov@ncfu.ru
ORCID iD: 0000-0002-6644-9949
Stavropol, Russia

N. A. Aksenov

North Caucasus Federal University

ORCID iD: 0000-0002-7125-9066
Stavropol, Russia

A. S. Akulova

North Caucasus Federal University

Stavropol, Russia

D. C. Makieva

North Caucasus Federal University

Stavropol, Russia

I. V. Aksenova

North Caucasus Federal University

ORCID iD: 0000-0002-8083-1407
Stavropol, Russia

N. A. Arutiunov

North Caucasus Federal University

ORCID iD: 0000-0003-2675-9093
Stavropol, Russia

D. A. Aksenov

North Caucasus Federal University

ORCID iD: 0000-0002-0727-9652
Stavropol, Russia

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

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