Chemical transformations of 3-bromoethyl-5,7-dimethyl2-oxaadamantan-1-ol in sulfuric acid

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Resumo

The reactions of 3-bromomethyl-5,7-dimethyl-2-oxaadamantan-1-ol in a 96% acid medium both in the presence and in the absence of nucleophiles were studied. During the reactions a number of structural transformations of the 2-oxaadamantane cage take place. The possibility of obtaining 1,2,3-trisubstituted adamantanes is also presented. The structural features of new compounds are investigated using 2D NMR spectroscopy and XRD analysis. The obtained compounds can be used in the directed synthesis of a new cage heterocycles for studying of biological activity.

Sobre autores

E. Ivleva

Samara State Technical University

Email: ivleva.ea@samgtu.ru

E. Simatova

Samara State Technical University

Email: ivleva.ea@samgtu.ru

M. Zaborskaya

Samara State Technical University

Email: ivleva.ea@samgtu.ru

M. Kazachkova

Samara State Technical University

Email: ivleva.ea@samgtu.ru

V. Rybakov

Lomonosov Moscow State University

Email: ivleva.ea@samgtu.ru

Yu. Klimochkin

Samara State Technical University

Email: ivleva.ea@samgtu.ru

Bibliografia

  1. Klapötke T.M., Krumm B., Widera A. ChemPlusChem. 2018, 83, 61-69. doi: 10.1002/cplu.201700542
  2. Harrison K.W., Rosenkoetter K.E., Harvey B.G. Energy Fuels. 2018, 32, 7786-7791. doi: 10.1021/acs.energyfuels.8b00792
  3. Xie J., Zhang X., Xie J., Xu J., Pan L., Zou J.-J. Fuel. 2019, 239, 652-658. doi: 10.1016/j.fuel.2018.11.064
  4. Agnew-Francis K.A., Williams C.M. Adv. Synth. Catal. 2016, 358, 675-700. doi. 10.1002/adsc.201500949
  5. Pavlov D., Sukhikh T., Filatov E., Potapov A. Molecules. 2019, 24, 2717-2728. doi: 10.3390/molecules24152717
  6. Parmar B., Patel P., Murali V., Rachuri Y., Kureshy R.I., Khan N.H., Suresh E. Inorg. Chem. Front. 2018, 5, 2630-2640. doi: 10.1039/C8QI00744F
  7. Zheng Y.-Z., Zheng Z., Tong M.-L., Chen X.-M. Polyhedron. 2013, 52, 1159-1168. doi: 10.1016/j.poly.2012.06.051
  8. Nasrallah H., Hierso J.-C. Chem. Mater. 2019, 31, 619-642. doi: 10.1021/acs.chemmater.8b04508
  9. Ryan L.S., Nakatsuka A., Lippert A.R. Results Chem. 2021, 3, 100106. doi: 10.1016/j.rechem.2021.100106
  10. Kagalwala H.N., Reeves R.T., Lippert A.R. Curr. Opin. Chem. Biol. 2022, 68, 102134. doi: 10.1016/j.cbpa.2022.102134
  11. Vacher M., Galván I.F., Ding B.-W., Schramm S., Berraud-Pache R., Naumov P., Ferré N., Liu Y.-J., Navizet I., Roca-Sanjuán D., Baader W.J., Lindh R. Chem. Rev. 2018, 118, 6927-6974. doi: 10.1021/acs.chemrev.7b00649
  12. Gu Y., Zhou X., Li Y., Wu K., Wang F., Huang M., Guo F., Wang Y., Gong S., Ma D., Yang C. Org. Electron. 2015, 25, 193-199. doi: 10.1016/j.orgel.2015.06.036
  13. Wanka L., Iqbal K., Schreiner P.R. Chem. Rev. 2013, 113, 3516-3604. doi: 10.1021/cr100264t
  14. Stockdale T.P., Williams C.M. Chem. Soc. Rev. 2015, 44, 7737-7763. doi: 10.1039/c4cs00477a
  15. Spilovska K., Zemek F., Korabecny J., Nepovimova E., Soukup O., Windisch M., Kuca K. Curr. Med. Chem. 2016, 23, 3245-3266. doi: 10.2174/0929867323666160525114026
  16. Lamoureux G., Artavia G. Curr. Med. Chem. 2010, 17, 2967-2978. doi: 10.2174/092986710792065027
  17. Zarubaev V.V., Golod E.L., Anfimov P.M., Shtro A.A., Saraev V.V., Gavrilov A.S., Logvinov A.V., Kiselev O.I. Bioorg. Med. Chem. 2010, 18, 839-848. doi: 10.1016/j.bmc.2009.11.047
  18. Suslov E.V., Mozhaytsev E.S., Korchagina D.V., Bormotov N.I., Yarovaya O.I., Volcho K.P., Serova O.A., Agafonov A.P., Maksyutov R.A., Shishkina L.N., Salakhutdinov N.F. RSC Med. Chem. 2020, 11, 1185-1195. doi: 10.1039/D0MD00108B
  19. Спасов А.А., Хамидова Т.В., Бугаева Л.И., Морозов И.С. Хим.-фарм. ж. 2000, 34, 3-9.
  20. Spasov A.A., Khamidova T.V., Bugaeva L.I., Morozov I.S. Pharm. Chem. J. 2000, 34, 1-7. doi: 10.1007/BF02524549
  21. Papanastasiou I., Tsotinis A., Kolocouris N., Nikas S.P., Vamvakides A. Med. Chem. Res. 2014, 23, 1966-1975. doi: 10.1007/s00044-013-0798-7
  22. Kadernani Y.E., Zindo F.T., Kapp E., Malan S.F., Joubert J. Med. Chem. Commun. 2014, 5, 1678-1684. doi: 10.1039/C4MD00244J
  23. Protopopova M., Hanrahan C., Nikonenko B., Samala R., Chen P., Gearhart J., Einck L., Nacy C.A.J. Antimicrob. Chemother. 2005, 56, 968-974. doi: 10.1093/jac/dki319
  24. Cheng H., Hoffman J., LeSajiv P., Nair K., Cripps S., Matthews J., Smith C., Yang M., Kupchinsky S., Dress K., Edwards M., Cole B., Walters E., Loh C., Ermolieff J., Fanjul A., Bhat G. B., Herrera J., Pauly T., Hosea N., Paderes G., Rejto P. Bioorg. Med. Chem. Lett. 2010, 20, 2897-2902. doi: 10.1016/j.bmcl.2010.03.032
  25. Dembitsky V.M., Gloriozova T.A., Poroikov V.V. Bio. Biophys. Res. Commun. 2020, 529, 1225-1241. doi: 10.1016/j.bbrc.2020.06.123
  26. Шокова Э.А., Ковалев В.В. Хим.-фарм. ж. 2016, 50, 3-15.
  27. Shokova Й. A., Kovalev V. V. Pharm. Chem. J. 2016, 50, 63-75. doi: 10.1007/s11094-016-1400-7
  28. Спасов А.А., Васильев П.М., Бабков Д.А., Прохорова Т.Ю., Стурова Е.А., Климочкин Ю.Н., Леонова М.В., Баймуратов М.Р. Биоорг. хим. 2017, 43, 420-426.
  29. Spasov A.A., Vasil'ev P.M., Babkov D.A., Prokhorova T.Y., Sturova E.A., Klimochkin Y.N., Leonova M.V., Baimuratov M.R. Russ. J. Bioorg. Chem. 2017, 43, 449-455. doi: 10.1134/S1068162017040124
  30. Liu Z., Yang S., Jin X., Zhang G., Guo B., Chen H., Yu P., Sun Y., Zhang Z., Wang Y. Med. Chem. Commun. 2017, 8, 135-147. doi: 10.1039/c6md00509h
  31. Ширяев В.А., Климочкин Ю.Н. ХГС. 2020, 56, 626-635.
  32. Shiryaev V.A., Klimochkin Y.N. Chem. Heterocycl. Compd. 2020, 56, 626-635. doi: 10.1007/s10593-020-02712-6
  33. Климочкин Ю.Н., Ширяев В.А., Леонова М.В. Изв. АН. Сер. хим. 2015, 64, 1473-1496.
  34. Klimochkin Y.N., Shiryaev V.A., Leonova M.V. Russ. Chem. Bull. 2015, 64, 1473-1496. doi: 10.1007/s11172-015-1035-y
  35. Shiryaev V.A., Skomorohov M.Yu., Leonova M.V., Bormotov N.I., Serova O.A., Shishkina L.N., Agafonov A.P., Maksyutov R.A., Klimochkin Y.N. Eur. J. Med. Chem. 2021, 221, 113485. doi: 10.1016/j.ejmech.2021.113485
  36. Shiryaev V.A., Radchenko E.V., Palyulin V.A., Zefirov N.S., Bormotov N.I., Serova O.A., Shishkina L.N., Baimuratov M.R., Bormasheva K.M., Gruzd Y.A., Ivleva E.A., Leonova M.V., Lukashenko A.V., Osipov D.V., Osyanin V.A., Reznikov A.N., Shadrikova V.A., Sibiryakova A.E., Tkachenko I.M., Klimochkin Y.N. Eur. J. Med. Chem. 2018, 158, 214-235. doi: 10.1016/j.ejmech.2018.08.009
  37. Duque M.D., Camps P., Profire L., Montaner S., Vázquez S., Sureda F.X., Mallol J., López-Querol M., Naesens L., De Clercq E., Prathalingam S.R., Kelly J.M. Bioorg. Med. Chem. 2009, 17, 3198-3206. doi: 10.1016/j.bmc.2009.02.007
  38. Leiva R., Gazzarrini S., Esplugas R., Moroni A., Naesens L., Sureda F.X., Vázquez S. Tetrahedron Lett. 2015, 56, 1272-1275. doi: 10.1016/j.tetlet.2015.01.160
  39. Codony S., Pujol E., Pizarro J., Feixas F., Valverde E., Loza M.I., Brea J.M., Saez E., Oyarzabal J., Pineda-Lucena A., Perez B., Perez C., Rodríguez-Franco M.I., Leiva R., Osuna S., Morisseau C., Hammock B.D., Vazquez-Carrera M., Vazquez S. J. Med. Chem. 2020, 63, 9237-9257. doi: 10.1021/acs.jmedchem.0c00310
  40. Ronco C., Jean L., Renard P.Y. Tetrahedron Lett. 2010, 66, 7399-7404. doi: 10.1016/j.tet.2010.07.021
  41. Ronco C., Foucault R., Gillon E., Bohn P., Nachon F., Jean L., Renard P.Y. ChemMedChem. 2011, 6, 876-888. doi: 10.1002/cmdc.201000523
  42. Mlinarić-Majerski K., Kragol G. Tetrahedron. 2001, 57, 449-457.
  43. Marchand A.P., Kumar K.A., McKim A.S. Tetrahedron. 1997, 53, 3467-3474. doi: 10.1016/S0040-4020(97)00075-6
  44. Ramljak T.S., Despotovic I., Mlinaric-Majerski K. Tetrahedron. 2013, 69, 10610-10620. doi: 10.1016/j.tet.2013.10.039
  45. Ивлева Е.А., Клепиков В.В., Хатмуллина Ю.Э., Рыбаков В.Б., Климочкин Ю.Н. ЖОрХ. 2022, 58, 51-60.
  46. Ivleva E.A., Klepikov V.V., Khatmullina Yu.E., Rybakov V.B., Klimochkin Yu.N. Russ. J. Org. Chem. 2022, 58, 38-46. doi: 10.1134/S1070428022010043
  47. Моисеев И.К., Дорошенко Р.И. ЖОрХ. 1983, 19, 1117-1118.
  48. Моисеев И.К., Багрий Е.И., Климочкин Ю.Н., Долгополова Т.Н., Трахтенберг П.Л., Земцова М.Н. Изв. АН. СССР. Сер. хим. 1985, 9, 2141-2143.
  49. Moiseev I.K., Bagrii E.I., Klimochkin Yu.N., Dolgopolova T.N., Zemtsova M.N., Trakhtenberg P.L. Russ. Chem. Bull. 1985, 9, 1980-1982. doi: 10.1007/BF00953950
  50. Ширяев А.К., Моисеев И.К. ЖОрХ. 2001, 37, 781-782.
  51. Shiryaev A.K., Moiseev I. K. Russ. J. Org. Chem. 2001, 37, 746-747. doi: 10.1023/A:1012428724127
  52. Моисеев И.К., Стулин Н.В., Юдашкин А.В., Климочкин Ю.Н. ЖОХ. 1985, 55, 1655-1656.
  53. Климочкин Ю.Н., Вологин М.Ф., Коржев И.Р., Багрий Е.И. Нефтехимия. 2001, 41, 30-32.
  54. Ивлева Е.А., Ткаченко И.М., Климочкин Ю.Н. ЖОрХ. 2016, 52, 1567-1572.
  55. Ivleva E.A., Tkachenko I.M., Klimochkin Yu.N. Russ. J. Org. Chem. 2016, 52, 1558-1564. doi: 10.1134/S1070428016110026
  56. Климочкин Ю.Н., Ивлева Е.А., Ширяев В.А. ЖОрХ. 2021, 57, 373-383.
  57. Klimochkin Y.N., Ivleva E.A., Shiryaev V.A. Russ. J. Org. Chem. 2021, 57, 355-363. doi: 10.1134/S1070428021030052
  58. Климочкин Ю.Н., Ивлева Е.А. ЖОрХ. 2022, 58, 484-494.
  59. Klimochkin Y.N., Ivleva E.A. Russ. J. Org. Chem. 2022, 58, 669-678. doi: 10.1134/S1070428022050050
  60. Ivleva E.A., Petrova E.V., Klimochkin Y.N., Rybakov V.B. CCDC 1921976: Experimental Crystal Structure Determination. CSD Commun. 2019. doi: 10.5517/ccdc.csd.cc22hz7t
  61. Юрченко А.Г., Мурзинова З.Н., Степанов Ф.Н. ЖОрХ. 1972, 8, 2332-2339.
  62. Юрченко А.Г., Мурзинова З.Н., Исаев С.Д. ЖОрХ. 1975, 11, 1427-1431.
  63. Sheldrick G.M. Acta Crystallogr., Sect. C. 2015, 71, 3-8. doi: 10.1107/S2053229614024218
  64. Farrugia L.J. J. Appl. Crystallogr. 2012, 45, 849-854. doi: 10.1107/S0021889812029111

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