Recyclization reaction of S-, N-containing cyclic peroxides with aromatic amines

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Аннотация

The recyclization reaction of tetraoxathiaspiroalkanes and tetraoxathiocanes with primary amines ( o , p -fluoroanilines, m , p -chloroanilines, o -toluidine, o , p -anisidines, ammonium chloride) to obtain cycloazadiperoxides under the action of samarium nitrate crystal hydrate as a catalyst was studied. The possibility of recycling N -( tert -butyl)hexaoxaazadispirocycloalkanes with arylamines to the corresponding azatriperoxides was shown. It was found that the rate of the recyclization reaction depends on the nature of the central heteroatom in the heterocycle (S > N > O).

Авторлар туралы

N. Makhmudiyarova

Institute of Petrochemistry and Catalysis UFIC RAS

Email: natali-mnn@mail.ru

I. Ishmukhametova

Institute of Petrochemistry and Catalysis UFIC RAS

Email: natali-mnn@mail.ru

Әдебиет тізімі

  1. Litvinov V.P. Russ. Chem. Rev. 1999, 68, 39-53.
  2. Brown D.J. Mechanisms of Molecular Migrations. New York: John Wiley and Sons. 1968, 1, 209.
  3. Vardanyan R.S., Hruby V.J. J. Heterocycl. Chem. 2005, 42, 557, 557-562. doi: 10.1515/HC.2011.025
  4. Babaev E.V. J. Heterocycl. Chem. 2000, 37, 519, 519-526.
  5. Makhmudiyarova N.N., Khatmullina G.M., Rakhimov R.Sh., Meshcheryakova E.S., Ibragimov A.G., Dzhemilev U.M. Tetrahedron. 2016, 72, 3277-3281. doi: 10.1016/j.tet.2016.04.055
  6. Makhmudiyarova N.N., Ishmukhametova I.R., Tyumkina T.V., Ibragimov A.G., Dzhemilev U.M. Tetrahedron Lett. 2018, 59, 3161-3164. doi: 10.1016/j.tetlet.2018.07.010
  7. Tyumkina T.V., Makhmudiyarova N.N., Kiyamutdinova G.M., Meshcheryakova E.S., Bikmukhametov K.Sh., Abdullin M.F., Khalilov L.M., Ibragimov A.G., Dzhemilev U.M. Tetrahedron. 2018, 74, 1749-1758. doi: 10.1016/j.tet.2018.01.045
  8. Makhmudiyarova N.N., Ishmukhametova I.R., Dzhemileva L.U., Tyumkina T.V., D'yakonov V.A., Ibragimov A.G., Dzhemilev U.M. RSC Adv. 2019, 9, 18923-18929. doi: 10.1039/c9ra02950h
  9. Махмудиярова Н.Н., Шангараев К.Р., Мещерякова E.С., Тюмкина T.В., Ибрагимов А.Г., Джемилев У.М. ХГС. 2019, 55, 1111-1119. doi: 10.1007/s10593-019-02586-3
  10. Makhmudiyarova N.N., Ishmukhametova I.R., Dzhemileva L.U., D'yakonov V.A., Ibragimov A.G., Dzhemilev U.M. Molecules. 2020, 25, 1874. doi: 10.3390/molecules25081874
  11. Махмудиярова Н.Н., Ишмухаметова И.Р., Джемилева Л.У., Дьяконов В.А., Ибрагимов А.Г., Джемилев У.М. ЖОрХ. 2020, 56, 746-752. doi: 10.1134/s1070428020050115
  12. Махмудиярова Н.Н., Ишмухаметова И.Р., Ибрагимов А.Г., Джемилев У.М. Докл. Акад. наук. 2020, 491, 93-100. doi: 10.31857/S2686953520040044
  13. Efferth T. Biotechnol. Adv. 2018, 36, 1730-1737. doi: 10.1016/j.biotechadv.2018.01.001
  14. Solaja B.A., Terzic N., Pocsfalvi G., Gerena L., Tinant B., Opsenica D., Milhous W. K. J. Med. Chem. 2002, 45, 3331-3336. doi: 10.1021/jm020891g
  15. D'Alessandro S., Scaccabarozzi D., Signorini L., Perego F., Ilboudo D.P., Ferrante P., Delbue S. Microorganisms. 2020, 8, 1. doi: 10.3390/microorganisms8010085
  16. Efferth T., Romero M.R., Wolf D.G., Stamminger T., Marin J.J.G., Marschall M. Clin. Infect. Dis. 2008, 47, 804-811. doi: 10.1086/591195
  17. Frohlich T., Reiter C., Saeed M.E.M., Hutterer C., Hahn F., Leidenberger M., Friedrich O., Kappes B., Marschall M., Efferth T., Tsogoeva S.B. ACS Med. Chem. Lett. 2018, 9, 534-539. doi: 10.1021/acsmedchemlett.7b00412
  18. Ghorai P., Dussault P.H., Hu C. Org. Lett. 2008, 10, 2401-2404. doi: 10.1021/ol800657m
  19. Wang X., Dong Y., Wittlin S., Charman S.A., Chiu F.C.K., Chollet J., Katneni K., Mannila J., Morizzi J., Ryan E., Scheurer C., Steuten J., Santo T.J., Snyder C., Vennerstrom J.L. J. Med. Chem. 2013, 56, 2547-2555. doi: 10.1021/jm400004u
  20. Ingram K., Yaremenko I.A., Krylov I.B., Hofer L., Terent'ev A.O., Keiser J. J. Med. Chem. 2012, 55, 8700-8711. doi: 10.1021/jm3009184
  21. Cowan N., Yaremenko I. A., Krylov I. B., Terent'ev A.O., Keiser J. Biorg. Med. Chem. 2015, 23, 5175-5181. doi: 10.1016/j.bmc.2015.02.010
  22. Brecht K., Kirchhofer C., Bouitbir J., Trapani F., Keiser J., Krahenbuhl S. Int. J. Mol. Sci. 2019, 20, 4880. doi: 10.3390/ijms20194880
  23. Wu J.B., Wang X.F., Chiu F.C.K., Haberli C., Shackleford D.M., Ryan E., Kamaraj S., Bulbule V.J., Wallick A.I., Dong Y.X., White K.L., Davis P.H., Charman S.A., Keiser J., Vennerstrom J.L. J. Med. Chem. 2020, 63, 3723-3736. doi: 10.1021/acs.jmedchem.0c00069
  24. Fisher L.C., Blackie M.A.L. Mini-Rev. Med. Chem. 2014, 14, 123-135. doi: 10.2174/1389557514666140123144942
  25. Hao H.D., Wittlin S., Wu Y.K. Chem. Eur. J. 2013, 19, 23, 7605-7619. doi: 10.1002/chem.201300076
  26. Jefford C.W. Curr. Top. Med. Chem. 2012, 12, 373-399. doi: 10.2174/156802612799362940
  27. Keiser J., Ingram K., Vargas M., Chollet J., Wang X.F., Dong Y.X., Vennerstrom J.L. Antimicrob. Agents Chemother. 2012, 56, 1090-1092. doi: 10.1128/AAC.05371-11
  28. Kuster T., Kriegel N., Stadelmann B., Wang X.F., Dong Y.X., Vennerstrom J.L., Keiser J., Hemphill A. Int. J. Antimicrob. Agents. 2014, 43, 40-46.
  29. Vil' V.A., Yaremenko I.A., Ilovaisky A.I., Terent'ev A.O. Molecules. 2017, 22, 1881. doi: 10.3390/molecules22111881
  30. Coghi P., Yaremenko I.A., Prommana P., Radulov P.S., Syroeshkin M.A., Wu Y.J., Gao J.Y., Gordillo F.M., Mok S., Wong V.K.W., Uthaipibull C., Terent'ev A.O. Chem. Med. Chem. 2018, 13, 902-908. doi: 10.1002/cmdc.201700804
  31. Yaremenko I.A., Coghi P., Prommana P., Qiu C.L., Radulov P.S., Qu Y.Q., Belyakova Y.Y., Zanforlin E., Kokorekin V.A., Wu Y.Y.J., Fleury F., Uthaipibull C., Wong V.K.W., Terent'ev A.O. Chem. Med. Chem. 2020, 15, 1118-1127.
  32. Brautigam M., Teusch N., Schenk T., Sheikh M., Aricioglu R.Z., Borowski S.H., Neudorfl J.M., Baumann U., Griesbeck A.G., Pietsch M. Chem. Med. Chem. 2015, 10, 629-639. doi: 10.1002/cmdc.201402553
  33. Abrams R.P., Carroll W.L., Woerpel K.A. ACS Chem. Biol. 2016, 11, 1305-1312. doi: 10.1021/acschembio.5b00900
  34. Chaudhari M.B., Moorthy S., Patil S., Bisht G.S., Mohamed H., Basu S., Gnanaprakasam B. J. Org. Chem. 2018, 83, 1358-1368. doi: 10.1021/acs.joc.7b02854
  35. Dwivedi A., Mazumder A., du Plessis L., du Preez J.L., Haynes R.K., du Plessis J. Nanomed. Nanotechnol. Biol. Med. 2015, 11, 2041-2050. doi: 10.1016/j.nano.2015.07.010
  36. Chaudhary S., Sharma V., Jaiswal P.K., Gaikwad A.N., Sinha S.K., Puri S.K., Sharon A., Maulik P.R., Chaturvedi V. Org. Lett. 2015, 17, 4948-4951. doi: 10.1021/acs.orglett.5b02296
  37. Miller M.J., Walz A.J., Zhu H., Wu C.R., Moraski G., Mollmann U., Tristani E.M., Crumbliss A.L., Ferdig M.T., Checkley L., Edwards R.L., Boshoff H.I. J. Am. Chem. Soc. 2011, 133, 2076-2079. doi: 10.1021/ja109665t
  38. Zhou F.W., Lei H.S., Fan L., Jiang L., Liu J., Peng X.M., Xu X.R., Chen L., Zhou C.H., Zou Y.Y., Liu C.P., He Z.Q., Yang D.C. Bioorg. Med. Chem. Lett. 2014, 24, 1912-1917. doi: 10.1016/j.bmcl.2014.03.010
  39. Cusati R.C., Barbosa L.C.A., Maltha C.R.A., Demuner A.J., Oliveros-Bastidas A., Silva A.A. Pest Manage Sci. 2015, 71, 1037-1048. doi: 10.1002/ps.3891
  40. Barbosa L.C.A., Maltha C.R.A., Cusati R.C., Teixeira R.R., Rodrigues F.F., Silva A.A., Drew M.G.B., Ismail F.M.D. J. Agric. Food Chem. 2009, 57, 10107-10115. doi: 10.1021/jf902540z
  41. Barbosa L.C.A., Pereira U.A., Teixeira R.R., Maltha C.R.A., Fernandes S.A., Forlani G. J. Agric. Food Chem. 2008, 56, 9434-9440. doi: 10.1021/jf802077e
  42. Yaremenko I.A., Radulov P.S., Belyakova Y.Y., Demina A.A., Fomenkov D.I., Barsukov D.V., Subbotina I.R., Fleury F., Terent'ev A.O. Chem. Eur. J. 2020, 26, 4734-4751. doi: 10.1002/chem.201904555
  43. Yaremenko I.A., Syromyatnikov M.Y., Radulov P.S., Belyakova Y.Y., Fomenkov D.I., Popov V.N., Terent'ev A.O. Molecules. 2020, 25, 1924. doi: 10.3390/molecules25081954
  44. Makhmudiyarova N.N., Ishmukhametova I.R., Shangaraev K.R., Dzhemileva L.U., D'yakonov V.A., Ibragimov A.G. Dzhemilev U.M. New J. Chem. 2021, 45, 2069-2077. doi: 10.1039/d0nj05511e
  45. Makhmudiyarova N.N., Shangaraev K.R., Dzhemileva L.U., Tuymkina T.V., Mescheryakova E.S., D'yakonov V.A., Ibragimov A.G., Dzhemilev U.M. RSC Adv. 2019, 9, 29949-29958. doi: 10.1039/c9ra06372b
  46. Yur'ev Yu.K. Ber. Deutsch. Chem. Ges. B. 1936, 69B, 440-443.
  47. Makhmudiyarova N.N., Shangaraev K.R., Ishmukhametova I.R., Ibragimov A.G., Dzhemilev U.M. RSC Adv. 2021, 11, 4235-4236. doi: 10.1039/d0ra09758f
  48. Kukushkin Yu.N. The Reactivity of Coordination Compounds. Leningrad: Khimiya 1987, 228.
  49. Pearson R.G. Russ. Chem. Rev. 1971, 40, 1259-1282. doi: 10.1021/ed055pA346.3
  50. Denekamp C., Gottlieb L., Tamiri T., Tsoglin A., Shilav R., Karon M. Org. Lett. 2005, 7, 2461-2464. doi: 10.1021/ol050801c
  51. Махмудиярова Н.Н., Рахимов Р.Ш., Тюмкина Т.В., Мещерякова Е.С., Ибрагимов А.Г., Джемилев У.М. ЖОрХ. 2019, 55, 713-727. doi: 10.1134/s1070428019050075

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