Three-Component Cyclization of Phenyl-1,3-dicarbonyls with α,β-Enaldehydes and 2-(Aminomethyl)aniline into Pyrido[2,1-b]quinazolines

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Abstract

Three-component reaction of phenyl-1,3-dicarbonyl compounds with α,β-unsaturated aldehydes and 2-(aminomethyl)aniline under mild conditions leads to regio- and chemoselective formation of trans- and cis-diastereomers of tetrahydro-7H-pyrido[2,1-b]quinazolines. In most cases these products were isolated individually. The spatial structure of the heterocycles was proved based on 1H, 13C, 2D 1H-13C HSQC/HMBC, 1H-1H NOESY NMR spectroscopy and X-ray diffraction data.

About the authors

S. O Kushch

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

ORCID iD: 0000-0002-7518-8998
Ekaterinburg, Russia

M. V Goryaeva

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

ORCID iD: 0000-0002-7853-688X
Ekaterinburg, Russia

Ya. V Burgart

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

ORCID iD: 0000-0001-6061-2410
Ekaterinburg, Russia

M. A Ezhikova

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

ORCID iD: 0000-0001-5689-5569
Ekaterinburg, Russia

M. I Kodess

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

ORCID iD: 0000-0003-4649-3659
Ekaterinburg, Russia

P. A Slepukhin

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

ORCID iD: 0000-0001-8132-9905
Ekaterinburg, Russia

O. V Koryakova

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

ORCID iD: 0000-0001-7081-8367
Ekaterinburg, Russia

I. N Ganebnykh

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

ORCID iD: 0000-0002-8487-8448
Ekaterinburg, Russia

V. I Saloutin

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: saloutin@ios.uran.ru
ORCID iD: 0000-0003-1976-7861
Ekaterinburg, Russia

References

  1. Sharma K., Sharma S.C., Kapoor M. ECS Transactions. 2022, 107, 9747–9761. https://doi.org/10.1149/10701.9747ecst
  2. Talbi S., Dib M., Bouissane L., Abderrafia H., Rabi S., Khouili M. Curr. Org. Synth. 2022, 19, 220–245. https://doi.org/10.2174/1570179418666211011141428
  3. Simon C., Constantieux T., Rodriguez J. Eur. J. Org. Chem. 2004, 4957–4980. https://doi.org/10.1002/ejoc.200400511
  4. Biginelli P. Chem. Ber. 1891, 24, 1312–1317.
  5. Kappe C.O. Tetrahedron. 1993, 49, 6937–6963. https://doi.org/10.1016/S0040-4020(01)87971-0
  6. Gulten S., Gezer U., Gundogan E.A. Lett. Org. Chem. 2020, 17, 366–371. https://doi.org/10.2174/1570178616666190819142221
  7. Бургарт Я.В., Кузуева О.Г., Прядеина М.В., Каппе К.О., Салоутин В.И. ЖОрХ. 2001, 37, 915–926.
  8. Burgart Ya.V., Kuzueva O.G., Pryadeina M.V., Kappe C.O., Saloutin V.I. Russ. J. Org. Chem. 2001, 37, 869–880. https://doi.org/10.1023/A:1012473901354
  9. Hantzsch A. Ber. Dtsch. Chem. Ges. 1890, 23, 1474–1476.
  10. Du X.-X., Zi Q.-X., Wu Y.-M., Jin Y., Lin J., Yan S.-J. Green Chem. 2019, 21, 1505–1516. https://doi.org/10.1039/C8GC03698E
  11. Dömling A., Al Qahtani A.D. in Multicomponent Reactions in Organic Synthesis, Eds J. Zhu, Q. Wang, M.-X. Wang, Wiley-VCH Verlag GMBH, Weinheim, 2015, p. 1. https://doi.org/10.1002/9783527678174.ch01
  12. Dömling A., Wang W., Wang K. Chem. Rev. 2012, 112, 3083–3135. https://doi.org/10.1021/cr100233r
  13. Ganem B., Acc. Chem. Res. 2009, 42, 463–472. https://doi.org/10.1021/ar800214s
  14. Кущ С.О., Горяева М.В., Бургарт Я.В., Салоутин В.И. Изв. АH. Сер. хим. 2023, 72, 103–129.
  15. Kushch S.O., Goryaeva M.V., Burgart Ya.V., Saloutin V.I. Russ. Chem. Bull. 2023, 72, 103–129. https://doi.org/10.1007/s11172-023-3717-1
  16. Кущ С.О., Горяева М.В., Бургарт Я.В., Триандафилова Г.А., Малышева К.О., Красных О.П., Герасимова Н.А., Евстигнеева Н.П., Салоутин В.И. Изв. АH. Сер. хим. 2022, 71, 1687–1700.
  17. Kushch S.O., Goryaeva M.V., Burgart Ya.V., Triandafilova G.A., Malysheva K.O., Krasnykh O.P., Gerasimova N.A., Evstigneeva N.P., Saloutin V.I. Russ. Chem. Bull. 2022, 71, 1687–1700. https://doi.org/10.1007/s11172-022-3579-y
  18. Горяева М.В., Кущ С.О., Бургарт Я.В., Салоутин В.И. Изв. АH. Сер. хим. 2020, 69, 2163–2166.
  19. Goryaeva M.V., Kushch S.O., Burgart Ya.V., Saloutin V.I. Russ. Chem. Bull. 2020, 69, 2163–2166. https://doi.org/10.1007/s11172-020-3016-z
  20. Goryaeva M.V., Kushch S.O., Khudina O.G., Burgart Ya.V., Ezhikova M.A., Kodess M.I., Slepukhin P.A., Volobueva A.S., Slita A.V., Esaulkova Ia.L., Misiurina M.A., Zarubaev V.V., Saloutin V.I. J. Fluorine Chem. 2021, 109686. https://doi.org/10.1016/j.jfluchem.2020.109686
  21. Saloutin V.I., Goryaeva M.V., Kushch S.O., Khudina O.G., Ezhikova M.A., Kodess M.I., Slepukhin P.A., Burgart Ya.V. Pure Appl. Chem. 2020, 92, 1265–1275. https://doi.org/10.1515/pac-2019-1216
  22. Кущ С.О., Горяева М.В., Сурнина Е.А., Бургарт Я.В., Салоутин В.И. ЖОрХ. 2024, 60, 120–131.
  23. Kushch S.O., Goryaeva M.V., Surnina E.A., Burgart Ya.V., Saloutin V.I. Russ. J. Org. Chem. 2023, 59, 2147–2156. https://doi.org/10.1134/S1070428023120126
  24. Кущ С.О., Горяева М.В., Бургарт Я.В., Ежикова М.А., Кодесс М.И., Слепухин П.А., Салоутин В.И. Изв. АH, Сер. хим. 2024, 73, 2953–2967.
  25. Kushch S.O., Goryaeva M.V., Burgart Ya.V., Ezhikova M.A., Kodess M.I., Slepukhin P.A., Saloutin V.I. Russ. Chem. Bull. 2024, 73, 2953–2967. https://doi.org/10.1007/s11172-024-4413-5
  26. Shakhidoyatov K.M., Elmuradov B.Z. Chem. Nat. Compd. 2014, 50, 781–800. https://doi.org/10.1007/s10600-014-1086-6
  27. Kshirsagar U.A. Org. Biomol. Chem. 2015, 13, 9336–9352. https://doi.org/10.1039/c5ob01379h
  28. Mikhalev A.I., Kon’shin M.E., Ovodenko L.A., Zaks A.S. Pharm. Chem. J. 1995, 29, 124–126. https://doi.org/10.1007/bf02226524
  29. Sen T., Neog K., Sarma S., Manna P., Boruah H.P.D., Gogoi P., Singh A.K. Bioorg. Med. Chem. 2018, 26, 4942–4951. https://doi.org/10.1016/j.bmc.2018.08.034
  30. Manikanttha M., Deepti K., Tej M.B., Tej M.B., Reddy A.G., Kapavarapu R., Barange D.K., Raog M.V.B., Pal M. J. Mol. Struct. 2023, 1280, 135044. https://doi.org/10.1016/j.molstruc.2023.135044
  31. Nepali K., Ojha R., Singh A., Budhiraja A., Bedi P.M.S., Dhar K.L. Lett. Drug Des. Discovery. 2013, 10, 522–528. https://doi.org/10.2174/1570180811310060008
  32. Shourkaei F.A., Ranjbar P.R., Foroumadi A., Shams F. J. Mol. Struct. 2024, 1308, 138083. https://doi.org/10.1016/j.molstruc.2024.138083
  33. Bathula R., Satla S.R., Kyatham R., Gangarapu K. Asian Pac. J. Cancer Prev. 2019, 21, 411–421. https://doi.org/10.31557/APJCP.2020.21.2.411
  34. Шленев Р.М., Филимонов С.И., Тарасов А.В., Данилова А.С., Агатьев П.А. ЖОрХ. 2016, 52, 257–260.
  35. Shlenev R.M., Filimonov S.I., Tarasov A.V., Danilova A.S., Agat’ev P.A. Russ. J. Org. Chem. 2016, 52, 240–243. https://doi.org/10.1134/S1070428016020147
  36. Hao W., Li K., Ye C., Yu W., Chang J. Org. Lett. 2022, 24, 3286–3290. https://doi.org/10.1021/acs.orglett.2c01183
  37. Yan G., Golden J.E. Org. Lett. 2018, 20, 4393–4396. https://doi.org/10.1021/acs.orglett.8b01275
  38. Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K., Puschmann H. J. Appl. Crystallogr. 2009, 42, 339–341. https://doi.org/10.1107/S0021889808042726
  39. Sheldrick G.M., Acta Crystallogr., Sect. A: Cryst. Phys. 2008, 64, 112–122. https://doi.org/10.1107/S0108767307043930

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