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Heteroannelated Enaminoketones Derived from 1,2,4-Triketone Analogs

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Abstract

The reaction of (perfluoroalkyl)furan-3(2H)-ones and β-diketone containing an acetal moiety with (hetero)aromatic 1,2-diamines was studied. Quinoxalines and pyrido[3,4-b]pyrazine bearing the enaminoketone fragment were ynthesized by the regioselective addition of a dinucleophile at the α-dicarbonyl moiety of polyketones. In the case of β-diketone containing acetal and ester groups, the conversion involves the α-ketoester moiety to form a quinoxalinyl-substituted 2,3-butanedione. All products were characterized by NMR spectroscopy and X-ray diffraction.

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REFERENCES

  1. Elassara, A.-Z.A. and El-Khair, A.A., Tetrahedron, 2003, vol. 59, p. 8463. https://doi.org/10.1016/S0040-4020(03)01201-8

    Article  CAS  Google Scholar 

  2. Kudyakova, Yu.S., Bazhin, D.N., Goryaeva, M.V., Burgart, Ya.V., and Saloutin, V.I., Russ. Chem. Rev., 2014, vol. 83, p. 120. https://doi.org/10.1070/RC2014v083n02ABEH004388

    Article  CAS  Google Scholar 

  3. Farghaly, T., Abo Alnaja, A.M., and Shaaban, M.R., Curr. Org. Synth., 2021, vol. 18, p. 639. https://doi.org/10.2174/1570179418666210512015725

    Article  CAS  PubMed  Google Scholar 

  4. Flick, A.C., Ding, H.X., Leverett, C.A., Kyne, R.E., Liu, Jr.K.K.-C., Fink, S.J., and O’Donnell, C.J., J. Med. Chem., 2017, vol. 60, p. 6480. https://doi.org/10.1021/acs.jmedchem.7b00010

    Article  CAS  PubMed  Google Scholar 

  5. Pilet, G., Tommasino, J.-B., Fenain, F., Matrak, R., and Médebielle, M., Dalton Trans., 2008, p. 5621. https://doi.org/10.1039/b805071f

  6. King, A.P., Gellineau, H.A., MacMillan, S.N., and Wilson, J.J., Dalton Trans., 2019, vol. 48, p. 5987. https://doi.org/10.1039/c8dt04606a

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Bazhin, D.N., Kudyakova, Y.S., Edilova, Y.O., Burgart, Y.V., and Saloutin, V.I., Russ. Chem. Bull., 2022, vol. 71, p. 1321. https://doi.org/10.1007/s11172-022-3539-6

    Article  CAS  Google Scholar 

  8. Saloutin, V.I., Edilova, Y.O., Kudyakova, Y.S., Burgart, Y.V., and Bazhin, D.N., Molecules, 2022, vol. 27, p. 7894. https://doi.org/10.3390/molecules27227894

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Iminov, R.T., Mashkov, A.V., Vyzir, I. I., Chalyk, B.A., Tverdokhlebov, A.V., Mykhailiuk, P.K., Babichenko, L.N., Tolmachev, A.A., Volovenko, Y.M., Biitseva, A., Shishkin, O.V., and Shishkina, S.V., Eur. J. Org. Chem., 2015, p. 886. https://doi.org/10.1002/ejoc.201403295

  10. Franco, M.S.F., Casagrande, G.A., Raminelli, C., Moura, S., Rossatto, M., Quina, F.H., Pereira, C.M.P., Flores, A.F.C., and Pizzuti, L., Synth. Commun., 2015, vol. 45, no. 6, p. 692. https://doi.org/10.1080/00397911.2014.978504

    Article  CAS  Google Scholar 

  11. Mittersteiner, M., Andrade, V. P., Zachow, L.L., Frizzo, C.P., Bonacorso, H.G., Martins, M.A.P., and Zanatta, N., J. Org. Chem., 2019, vol. 84, no. 14, p. 8976. https://doi.org/10.1021/acs.joc.9b00867

    Article  CAS  PubMed  Google Scholar 

  12. Plaçais, C., Donnard, M., Panossian, A., Vors, J.-P., Bernier, D., Pazenok, S., and Leroux, F.R., Org. Lett., 2021, vol. 23, no. 12, p. 4915. https://doi.org/10.1021/acs.orglett.1c01672

  13. Filyakova, V.I., Boltacheva, N.S., Slepukhin, P.A., Pervova, M.G., and Charushin, V.N., Mendeleev Commun., 2020, vol. 30, p. 676. https://doi.org/10.1016/j.mencom.2020.09.042

    Article  CAS  Google Scholar 

  14. Yang, T., Deng, Z., Wang, K.-H., Li, P., Huang, D., Su, Y., and Hu, Y., J. Org. Chem., 2020, vol. 85. no. 2, p. 924. https://doi.org/10.1021/acs.joc.9b02873

    Article  CAS  PubMed  Google Scholar 

  15. Obydennov, D.L., El-Tantawy, A.I., and Sosnovskikh, V.Y., J. Org. Chem., 2018, vol. 83, no. 22, p. 13776. https://doi.org/10.1021/acs.joc.8b02075

    Article  CAS  Google Scholar 

  16. Obydennov, D.L., El-Tantawy, A.I., and Sosnovskikh, V.Y., New J. Chem., 2018, vol. 42, no. 11, p. 8943. https://doi.org/10.1039/c8nj01044g

    Article  CAS  Google Scholar 

  17. Kharrat, S.E., Laurent, P., and Blancou, H., Tetrahedron, 2014, vol. 70, no. 6, p. 1252. https://doi.org/10.1016/j.tet.2013.12.073

    Article  CAS  Google Scholar 

  18. Kappenberg, Y.G., Ketzer, A., Stefanello, F.S., Salbego, P.R.S., Acunha, T.V., Abbadi, B.L., Bizarro, C.V., Basso, L.A., Machado, P., Martins, M.A.P., Zanatta, N., Iglesias, B.A., and Bonacorso, H.G., New J. Chem., 2019, vol. 43, no. 31, p. 12375. https://doi.org/10.1039/c9nj01681c

    Article  CAS  Google Scholar 

  19. Moraes, P.A., Lobo, M.M., Marangoni, M.A., Meyer, A.R., Frizzo, C.P., Bonacorso, H.G., Martins, M.A.P., and Zanatta, N., Org. Biomol. Chem., 2019, vol. 17, p. 2384. https://doi.org/10.1039/c9ob00234k

    Article  CAS  PubMed  Google Scholar 

  20. Moraes, P.A., Brum, E.S., Brusco, I., Marangoni, M.A., Lobo, M.M., Camargo, A.F., Nogara, P.A., Bonacorso, H.G., Martins, M.A.P., Da Rocha, J.B.T., Oliveira, S.M., and Zanatta, N., ChemistrySelect, 2020, vol. 5, no. 46, p. 14620. https://doi.org/10.1002/slct.202004049

    Article  CAS  Google Scholar 

  21. Khlebnicova, T.S., Piven, Y.A., Baranovsky, A.V., Lakhvich, F.A., Sorokina, I.V., and Tolstikova, T.G., Steroids, 2019, vol. 147, p. 62. https://doi.org/10.1016/j.steroids.2018.10.001

    Article  CAS  PubMed  Google Scholar 

  22. Khlebnikova, T.S., Piven’, Y.A., Lakhvich, F.A., Frolova, T.S., Sorokina, I.V., and Tolstikova, T.G., Chem. Nat. Compd., 2018, vol. 54, p. 1100. https://doi.org/10.1007/s10600-018-2565-y

    Article  CAS  Google Scholar 

  23. Chopin, N., Novitchi, G., Me´debielle, M., and Pilet, G., J. Fluorine Chem., 2015, vol. 179, p. 169. https://doi.org/10.1016/j.jfluchem.2015.06.023

    Article  CAS  Google Scholar 

  24. Yoshihara, D., Karasawa, S., and Koga, N., J. Am. Chem. Soc., 2008, vol. 130, no. 32, p. 10460. https://doi.org/10.1021/ja802895d

    Article  CAS  PubMed  Google Scholar 

  25. Chibotaru, L.F., Ungur, L., Aronica, C., Elmoll, H., Pilet, G., and Luneau, D., J. Am. Chem. Soc., 2008, vol. 130, no. 37, p. 12445. https://doi.org/10.1021/ja8029416

    Article  CAS  PubMed  Google Scholar 

  26. Aronica, C., Jeanneau, E., Moll, H. E., Luneau, D., Gillon, B., Goujon, A., Cousson, A., Carvajal, M.A., and Robert, V., Chem. Eur. J., 2007, vol. 13, no. 13, p. 3666. https://doi.org/10.1002/chem.200601253

    Article  CAS  PubMed  Google Scholar 

  27. Aronica, C., Pilet, G., Chastanet, G., Wernsdorfer, W., Jacquot, J.-F., and Luneau, D., Angew. Chem. Int. Ed., 2006, vol. 45, no. 28, p. 4659. https://doi.org/10.1002/anie.200600513

    Article  CAS  Google Scholar 

  28. Nikolaeva, N.S., Kuratieva, N.V., Vikulova, E.S., Stabnikov, P.A., and Morozova, N.B., Polyhedron, 2019, vol. 171, p. 455. https://doi.org/10.1016/j.poly.2019.07.039

    Article  CAS  Google Scholar 

  29. Podhorsky, J., Murauskas, T., Hegemann, C., Graf, D., Fischer, T., Babiak, M., Pinkas, J., Plausinaitiene, V., Mathur, S., Abrutis, A., and Moravec, Z., Eur. J. Inorg. Chem., 2018, p. 5027. https://doi.org/10.1002/ejic.201800913

  30. Ojelere, O., Graf, D., Ludwig, T., Vogt, N., Klein, A., and Mathur, S., Dalton Trans., 2018, vol. 47, no. 19, p. 6842. https://doi.org/10.1039/c8dt00848e

    Article  CAS  PubMed  Google Scholar 

  31. Beckmann, U., Lindner, M.M., Eichberger, E., and Frank, W., J. Organomet. Chem., 2012, vol. 720, p. 73. https://doi.org/10.1016/j.jorganchem.2012.08.030

    Article  CAS  Google Scholar 

  32. Rezayee, N.M., Gerling, K.A., Rheingold, A.L., and Fritsch, J.M., Dalton Trans., 2013, vol. 42, no. 15, p. 5573. https://doi.org/10.1039/c3dt32314e

    Article  CAS  PubMed  Google Scholar 

  33. Obydennov, D.L., Chernyshova, E.V., and Sosnovskikh, V.Y., Chem. Heterocycl. Comp., 2020, vol. 56, no. 10, p. 1241. https://doi.org/10.1007/s10593-020-02807-0

    Article  CAS  Google Scholar 

  34. Beckmann, U., Eichberger, E., Lindner, M., Bongartz, M., and Kunz, P.C., Eur. J. Org. Chem., 2008, p. 4139. https://doi.org/10.1002/ejoc.200800372

  35. Chipanina, N.N., Oznobikhina, L.P., Aksamentova, T.N., Romanov, A.R., and Rulev, A.Yu., Tetrahedron, 2014, vol. 70, p. 1207. https://doi.org/10.1016/j.tet.2013.12.061

    Article  CAS  Google Scholar 

  36. Khlebnikova, T.S., Piven’, Y.A., Isakova, V.G., and Lakhvich, F.A., Russ. J. Org. Chem., 2012, vol. 48, no. 10, p. 1277. https://doi.org/10.1134/S107042801210003X

    Article  CAS  Google Scholar 

  37. Irgashev, R.A., Safrygin, A.V., Ezhikova, M.A., Kodess, M.I., Röschenthaler, G.-V., and Sosnovskikh, V.Y., Tetrahedron, 2015, vol. 71, p. 1822. https://doi.org/10.1016/j.tet.2015.02.010

    Article  CAS  Google Scholar 

  38. Safrygin, A.V., Barabanov, M.A., Irgashev, R.A., and Sosnovskikh, V.Ya., Chem. Heterocycl. Comp., 2015, vol. 51, p. 838. https://doi.org/10.1007/s10593-015-1784-4

    Article  CAS  Google Scholar 

  39. Bazhin, D.N., Kudyakova, Y.S., Röschenthaler, G.-V., Burgart, Y.V., Slepukhin, P.A., Isenov, M.L., Saloutin, V.I., and Charushin, V.N., Eur. J. Org. Chem., 2015, p. 5236. https://doi.org/10.1002/ejoc.201500737

  40. Kudyakova, Y.S., Onoprienko, A.Y., Slepukhin, P.A., Burgart, Y.V., Saloutin, V.I., and Bazhin, D.N., Chem. Heterocycl. Comp., 2019, vol. 55, p. 517. https://doi.org/10.1007/s10593-019-02488-4

    Article  CAS  Google Scholar 

  41. Kudyakova, Yu.S., Onoprienko, A.Ya., Edilova, Yu.O., Burgart, Ya.V., Saloutin, V.I., and Bazhin, D.N., Russ. Chem. Bull., 2021, vol. 70, p. 745. https://doi.org/10.1007/s11172-021-3145-z

    Article  CAS  Google Scholar 

  42. Sheldrick, G.M., Acta Crystallogr., Ser. A, 2008, vol. 64, p. 112. https://doi.org/10.1107/S0108767307043930

    Article  CAS  Google Scholar 

  43. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

  44. Berens, U., Leckel, D., and Oepen, S.C., J. Org. Chem., 1995, vol. 60, p. 8204

    Article  CAS  Google Scholar 

  45. Bazhin, D.N., Chizhov, D.L., Röschenthaler, G.-V., Kudyakova, Y.S., Burgart, Y.V., Slepukhin, P.A., Saloutin, V.I., and Charushin, V.N., Tetrahedron Lett., 2014, vol. 55, no. 42, p. 5714. https://doi.org/10.1016/j.tetlet.2014.08.046

    Article  CAS  Google Scholar 

  46. Bazhin, D.N., Kudyakova, Y.S., Burgart, Y.V., and Saloutin, V.I., Russ. Chem. Bull., 2018, vol. 68, p. 497. https://doi.org/10.1007/s11172-018-2099-2

    Article  CAS  Google Scholar 

  47. Edilova, Y.O., Kudyakova, Y.S., Kiskin, M.A., Burgart, Y.V., Saloutin, V.I., and Bazhin, D.N., J. Fluorine Chem., 2022, vol. 253. 109932. https://doi.org/10.1016/j.jfluchem.2021.109932

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ACKNOWLEDGMENTS

The work was carried out using the equipment of the “Spectroscopy and Analysis of Organic Compounds” Center for Collective Use.

Funding

The work was financially supported by the Russian Science Foundation (project no. 23-23-00425, https://rscf.ru/en/project/23-23-00425/)).

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Authors and Affiliations

  1. Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 620108, Yekaterinburg, Russia

    Yu. O. Edilova, Yu. S. Kudyakova, P. A. Slepukhin, V. I. Saloutin & D. N. Bazhin

  2. Ural Federal University named after the First President of Russia B.N. Eltsin, 620002, Yekaterinburg, Russia

    P. A. Slepukhin & D. N. Bazhin

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  1. Yu. O. Edilova
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  2. Yu. S. Kudyakova
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Correspondence to D. N. Bazhin.

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Edilova, Y.O., Kudyakova, Y.S., Slepukhin, P.A. et al. Heteroannelated Enaminoketones Derived from 1,2,4-Triketone Analogs. Russ J Gen Chem 93 (Suppl 1), S10–S18 (2023). https://doi.org/10.1134/S1070363223140098

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