Alkenylation of hydroxy derivatives of adamantane with alcohols in the presence of sulfuric acid

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Abstract

A series of adamantyl-containing alkenes was synthesized by alkenylation of 1-adamantanol with secondary alcohols in the presence of sulfuric acid. The boundaries of this reaction are shown, and it is revealed that in the case of using symmetrical dialkylcarbinols, alkenylation occurs selectively. When 1-adamantanol is alkenylated with sec-amyl alcohol and higher homologues, the formation of mixtures of isomeric alkenes is observed. The reactions of substituted adamantanols with isopropanol, 2-butanol and cyclohexanol in the presence of sulfuric acid were studied, and a series of new unsaturated derivatives of the adamantane series were obtained.

About the authors

M. R. Baimuratov

Samara State Technical University

Author for correspondence.
Email: baymuratovmr@yandex.ru
Russian Federation, ul. Molodogvardeiskaya, 244, Samara, 443100

U. M. Aristova

Samara State Technical University

Email: baymuratovmr@yandex.ru
ORCID iD: 0000-0001-5599-6579
Russian Federation, ul. Molodogvardeiskaya, 244, Samara, 443100

M. S. Shishkina

Samara State Technical University

Email: baymuratovmr@yandex.ru
Russian Federation, ul. Molodogvardeiskaya, 244, Samara, 443100

M. V. Leonova

Samara State Technical University

Email: baymuratovmr@yandex.ru
ORCID iD: 0000-0003-1831-9610
Russian Federation, ul. Molodogvardeiskaya, 244, Samara, 443100

Yu. N. Klimochkin

Samara State Technical University

Email: baymuratovmr@yandex.ru
ORCID iD: 0000-0002-7335-4040
Russian Federation, ul. Molodogvardeiskaya, 244, Samara, 443100

References

  1. Wanka L., Iqbal K., Schreiner P.R.Chem. Rev. 2013, 113, 3516–3604. doi: 10.1021/cr100264t
  2. Lamoureux G., Artavia G. Curr. Med. Chem. 2010, 17, 2967–2978. doi: 10.2174/092986710792065027
  3. Stockdale T.P., Williams C.M. Chem. Soc. Rev. 2015, 44, 7737–7763. doi: 10.1039/C4CS00477A
  4. Spilovska K., Zemek F., Korabecny J. Curr. Med. Chem. 2016, 23, 3245–3266. doi: 10.2174/0929867323666160525114026
  5. Taylor R.D., MacCoss M., Lawson A.D.G. J.Med. Chеm. 2014, 57, 5845–5859. doi: 10.1021/jm4017625
  6. Климочкин Ю.Н., Ширяев В.А., Леонова М.В.Изв. АН. Сер хим. 2015, 7, 1473–1496. [Klimochkin Yu.N., Shiryaev V.A., Leonova M.V. Russ. Chem. Bull. 2015, 64, 1473–1496.] doi: 10.1007/s11172-015-1035-y
  7. Foti C., Romita P., Borghi A., Angelini G., Bonamonte D. Dermatol. Ther.: Review. 2015, 28, 323–329. doi: 10.1111/dth.12282
  8. Liu J., Obando D., Liao V., Lifa T., Codd R. Eur. J. Med. Chem. 2011, 46, 1949–1963. doi 10.1016 / j.ejmech.2011.01.047
  9. 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. [Spasov A.A., Vasil’ev P.M., Babkov D.A., Prokhorova T.Yu., Sturova E.A., Klimochkin Yu. N., Leonova M.V., Baimuratov M.R. Russ. J. Bioorg. Chem. 2017, 43, 449–455.] doi: 10.1134/S1068162017040124
  10. Fang C., Xiong Y., Li Y., Chen Y., Liu J., Zhang H., Adedosu T.A., Peng P. Geochim. Cosmochim. Acta. 2013, 120, 109–120. doi: 10.1016/j.gca.2013.06.027
  11. Harrison K.W., Rosenkoetter K.E., Harvey B.G. Energy Fuels. 2018, 32, 7786–7791. doi: 10.1021/acs.energyfuels.8b00792
  12. Creton C. Macromolecules. 2017, 50, 8297–8316. doi: 10.1021/acs.macromol.7b01698
  13. Ивлева Е.А., Баймуратов М.Р., Журавлева Ю.А., Климочкин Ю.Н., Куликова И.А., Поздняков В.В., Шейкина Н.А., Тыщенко В.А. ЖОХ. 2014, 84, 2048–2050 [Ivleva E.A., Baimuratov M.R., Zhuravleva Yu.A., Klimochkin Yu.N., Kulikova I.A., Pozdnyakov V.V., Sheikina N.A., Tyshchenko V.A.Russ. J. Gen. Chem. 2014, 84, 2464–2466.] doi: 10.1134/S1070363214120226
  14. Jeong H.Y., Lee Y.K., Talaie A., Kim K.M., Kwon Y.D., Jang Y.R., Yoo K.H., Choo D.J., Jang J. Thin Solid Films. 2002, 417, 171-174. doi: 10.1016/S0040-6090(02)00569-2
  15. García-López V., Alemany L.B., Chiang P.T., Sun J., Chu P.L., Martí A.A., Tour J.M. Tetrahedron 2017, 73, 4864–4873. doi: 10.1016/j.tet.2017.05.063
  16. Багрий Е.И., Сагинаев А.Т.Успехи хим. 1983, 52, 1538–1567 [Bagrii E.I., Saginaev A.T. Russ. Chem. Rev., 1983, 52, 881–896.] doi: 10.1070/RC1983v052n09ABEH002898
  17. Леонова М.В., Белая Н.В., Баймуратов М.Р., Климочкин Ю.Н. ЖОрХ. 2018, 54, 1642-1648. [Leonova M.V., Belaya N.V., Baimuratov M.R., Klimochkin Yu.N. Russ. J. Org. Chem. 2018, 54, 1643–1651.] doi: 10.1134/S1070428018110040
  18. Леонова М.В., Баймуратов М.Р., Головин Е.В., Климочкин Ю.Н. ЖОрХ. 2014, 50, 194–197. [Leonova M.V., Baimuratov M.R., Golovin E.V., Klimochkin Yu.N. Russ. J. Org. Chem. 2014, 50, 183–186.] doi: 10.1134/S1070428014020079
  19. Баймуратов М.Р., Леонова М.В., Рыбаков В.Б., Климочкин Ю.Н. ХГС. 2015, 51, 582–585. [Baimuratov M.R., Leonova M.V., Rybakov V.B., Klimochkin Yu.N. Chem. Heterocycl. Compd. 2015, 51, 582–585.] doi: 10.1007/s10593-015-1740-3
  20. Baimuratov M.R., Leonova M.V., Shiryaev V.A., Klimochkin Yu.N. Tetrahedron. 2017, 73, 6101–6108. doi: 10.1016/j.tet.2017.08.025
  21. Баймуратов М.Р., Леонова М.В., Климочкин Ю.Н. ХГС. 2021, 57, 298–304. [Baimuratov M.R., Leonova M.V., Klimochkin Yu.N. Chem. Heterocycl. Compd. 2021, 57, 298–304.] doi: 10.1007/s10593-021-02907-5
  22. Хуснутдинов Р.И., Щаднева Н.А.Успехи хим. 2019, 88, 800–836. [Khusnutdinov R.I., Shchadneva N.A. Russ. Chem. Rev. 2019, 88, 800–836.] doi: 10.1070/RCR4881
  23. Ковалев В.В., Шокова Э.А. ЖОрХ. 1981, 17, 109–116.
  24. Климочкин Ю.Н., Багрий Е.И, Коржев И.Р., Вологин М.Ф. Нефтехимия 2001, 41, 34–35.
  25. Geluk H.W., Schlatmann J.L.M.A. Tetrahedron. 1968, 24, 5361–5368. doi: 10.1016/S0040-4020(01)96329-X
  26. Geluk H.W., Schlatmann J.L.M.A. Rec. Trav. Chim. 1971, 90, 516–520. doi: 10.1002/recl.19710900507
  27. Cuddy B.D., Grant D., Karim A., McKervey M.A., Rea. E.J.F.J.Chem. Soc., Perkin Trans. 1. 1972, 2701–2707. doi: 10.1039/P19720002701
  28. Ishii Y., Kato S., Iwahama T., Sakaguchi S. Tetrahedron Lett. 1996, 37, 4993–4996. doi: 10.1016/0040-4039(96)00992-6
  29. Ishii Y., Sakaguchi S. Catalys. Surveys Japan. 1999, 3, 27–35. doi: 10.1023/A:1019059315516
  30. Ивлева Е.А., Погуляйко А.В., Климочкин Ю.Н. ЖОрХ. 2018, 54, 1283–1289. [Ivleva E.A., Pogulyaiko A.V., Klimochkin Yu.N. Russ. J. Org. Chem. 2018, 54, 1294–1300.] doi: 10.1134/S107042801809004X
  31. Климочкин Ю.Н., Юдашкин А.В., Жилкина Е.О., Ивлева Е.А., Моисеев И.К., Ошис Я.Ф. ЖОрХ. 2017, 53, 959–964. [Klimochkin Yu.N., Yudashkin A.V., Zhilkina E.O., Ivleva E.A., Moiseev I.K., Oshis Ya.F. Russ. J. Org. Chem. 2017, 53, 971–976.] doi: 10.1134/S1070428017070028
  32. Федоренко А.В., Довгань Н.Л. Вестник Киевского политех. института: Хим. машиностроение и технол. 1983, 20, 11–15.
  33. Степанов Ф.Н., Сидорова Л.И., Довгань Н.Л. ЖОрХ. 1973, 9, 1545.
  34. Заикин В.Г., Соловьев В.Н., сметанин В.И., Багрий Е.И., Санин П.И. Изв. АН СССР. Сер. хим. 1975, 7, 1633–1636.

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