NOVEL EFFICIENT SYNTHETIC PATHWAY (+)‑CAMPHOR AND (–)‑FENCHONE ANILS UNDER HOMOGENOUS CATALYSIS

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Тек жазылушылар үшін

Аннотация

An efficient approach to the synthesis of (+)-camphor and (–)‑fenchone anils has been developed, which consists in the interaction of the corresponding bicyclic monoterpenoid ketones with substituted anilines in the presence of the (i-PrO)2Ti(OTf)2·(i-PrOH)2 complex obtained in situ, as a homophasic catalyst, and (i‑PrO)4Ti, as a dehydrating agent. The advantage of the proposed method lies not only in obtaining target products with good yields and high purity, but also in a simplified procedure for isolating target substances, which, in turn, are of interest as pharmacologically active compounds, antioxidants for rubber compounds and components of compositions for 3D-print.

Авторлар туралы

A. Vernigora

Volgograd State Technical University

Хат алмасуға жауапты Автор.
Email: vernigora.andreyy@gmail.com
Russian, 400005, Volgograd

R. Brunilin

Volgograd State Technical University

Email: vernigora.andreyy@gmail.com
Russian, 400005, Volgograd

V. Burmistrov

Volgograd State Technical University

Email: vernigora.andreyy@gmail.com
Russian, 400005, Volgograd

A. Davidenko

Volgograd State Technical University

Email: vernigora.andreyy@gmail.com
Russian, 400005, Volgograd

M. Nawrozkij

Sirius University of Science and Technology

Email: vernigora.andreyy@gmail.com
Russian, 354340, Krasnodar, Sirius Federal Territory

N. Salykin

Volgograd State Technical University

Email: vernigora.andreyy@gmail.com
Russian, 400005, Volgograd

V. Chernyshov

Sirius University of Science and Technology; Novosibirsk State University

Email: vernigora.andreyy@gmail.com
Russian, 354340, Krasnodar, Sirius Federal Territory; Russian, 630090, Novosibirsk

I. Novakov

Volgograd State Technical University

Email: vernigora.andreyy@gmail.com
Russian, 400005, Volgograd

Әдебиет тізімі

  1. Chernyshov V.V., Popadyuk I.I., Yarovaya O.I., Salakhutdinov N.F. // Top. Curr. Chem. 2022. V. 380. № 5. P. 42. https://doi.org/10.1007/s41061-022-00399-1
  2. Yarovaya O.I., Salakhutdinov N.F. // Russ. Chem. Rev. 2021. V. 90. № 4. P. 488–510. https://doi.org/10.1070/RCR4969
  3. Машковский М.Д. Лекарственные средства. 16-е изд., перераб., испр. и доп. М.: Изд-во Новая волна, 2012. 1216 с.
  4. Zielińska-Błajet M., Feder-Kubis J. // Int. J. Mol. Sci. 2020. V. 21. № 19. P. 7078. https://doi.org/10.3390/ijms21197078
  5. Sokolova A.S., Yarovaya O.I., Baev D.S., Shernyukov A.V., Shtro A.A., Zarubaev V.V., Salakhutdinov N.F. // Eur. J. Med. Chem. 2017. V. 127. P. 661–670. https://doi.org/10.1016/j.ejmech.2016.10.035
  6. Sokolova A.S., Yarovaya O.I., Shernyukov A.V., Gatilov Y.V., Razumova Y.V., Zarubaev V.V., Tretiak T.S., Pokrovsky A.G., Kiselev O.I., Salakhutdinov N.F. // Eur. J. Med. Chem. 2015. V. 105. P. 263–273. https://doi.org/10.1016/j.ejmech.2015.10.010
  7. Sokolova A.S., Yarovaya O.I., Shernyukov A.V., Pokrovsky M.A., Pokrovsky A.G., Lavrinenko V.A., Zarubaev V.V., Tretiak T.S., Anfimov P.M., Kiselev O.I., Beklemishev A.B., Salakhutdinov N.F. // Bioorg. Med. Chem. 2013. V. 21. № 21. P. 6690–6698. https://doi.org/10.1016/j.bmc.2013.08.014
  8. Artyushin O.I., Sharova E.V., Vinogradova N.M., Genkina G.K., Moiseeva A.A., Klemenkova Z.S., Orshan-skaya I.R., Shtro A.A., Kadyrova R.A., Zarubaev V.V., Yarovaya O.I., Salakhutdinov N.F., Brel V.K. // Bioorg. Med. Chem. Lett. 2017. V. 27. № 10. P. 2181–2184. https://doi.org/10.1016/j.bmcl.2017.03.051
  9. Artyushin O.I., Moiseeva A.A., Zarubaev V.V., Slita A.V., Galochkina A.V., Muryleva A.A., Borisevich S.S., Yarovaya O.I., Salakhutdinov N.F., Brel V.K. // Chem. Biodivers. 2019. V. 16. № 11. P. e1900340. https://doi.org/10.1002/cbdv.201900340
  10. Da Silva E., Da Silva Araújo A., Moraes A., De Souza L., Silva Lourenço M., De Souza M., Wardell J., Wardell S. // Sci. Pharm. 2016. V. 84. № 3. P. 467–483. https://doi.org/10.3390/scipharm84030467
  11. Вернигора А.А., Нилидин Д.А., Давиденко А.В., Фан Нгок Ту, Губин С.Г., Губина Е.В., Ваниев М.А., Новаков И.А. // Изв. ВолгГТУ. 2021. V. 252. № 5. С. 47–52. https://doi.org/10.35211/1990-5297-2021-5-252-47-52
  12. Winfield S. Age resistor. Пaтeнт US 2211629A. 1936.
  13. Chernyshov V.V., Yarovaya O.I., Vatsadze S.Z., Borise-vich S.S., Trukhan S.N., Gatilov Yu.V., Peshkov R.Yu., Eltsov I.V., Martyanov O.N., Salakhutdinov N.F. // European J. Org. Chem. 2021. V. 2021. № 3. P. 452–463. https://doi.org/10.1002/ejoc.202001397
  14. Zhou J., Liu X., Sun Z. // Heterocycles. 2016. V. 92. № 5. P. 944–953. https://doi.org/10.3987/COM-16-13434
  15. Strekowski L., Patterson S.E., Janda L., Wydra R.L., Harden D.B., Lipowska M., Cegla M.T. // J. Org. Chem. 1992. V. 57. № 1. P. 196–201. https://doi.org/10.1021/jo00027a037
  16. Love B.E., Ren J. // J. Org. Chem. 1993. V. 58. № 20. P. 5556–5557. https://doi.org/10.1021/jo00072a051
  17. Schmitt J., Suquet M., Callet G., Raveux R. // Bull. Soc. Chim. Fr. 1962. P. 444–455.
  18. Sokolova A.S., Yarovaya O.I., Korchagina D.V., Zarubaev V.V., Tretiak T.S., Anfimov P.M., Kiselev O.I., Salakhutdinov N.F. // Bioorganic Med. Chem. 2014. V. 22. № 7. P. 2141–2148. https://doi.org/10.1016/j.bmc.2014.02.038
  19. Raza Z., Dakovic S., Vinkovic V., Sunjic V. // Croat. Chem. Acta. 1996. V. 69. P. 1545–1559.
  20. Delogu G., De Lucchi O., Fois M.P., Valle G. // Phosphorus. Sulfur. Silicon Relat. Elem. 1990. V. 47. № 3–4. P. 417–425. https://doi.org/10.1080/10426509008037997
  21. Love B.E., Boston T.S., Nguyen B.T., Rorer J.R. // Org. Prep. Proced. Int. 1999. V. 31. № 4. P. 399–405. https://doi.org/10.1080/00304949909355728
  22. Guziec F.S., Moustakis C.A. // J. Chem. Soc., Chem. Commun. 1984. № 1. P. 63–64. https://doi.org/10.1039/C39840000063
  23. Hiroi K., Watanabe K. // Tetrahedron Asymmetry. 2001. V. 12. № 22. P. 3067–3071. https://doi.org/10.1016/S0957-4166(01)00546-8
  24. Motoyama Y., Tanaka M., Mikami K. // Inorg. Chim. Acta. 1997. V. 256. № 2. P. 161–163. https://doi.org/10.1016/S0020-1693(97)05471-6
  25. Reddelien M. // Chem. Ber. 1920. V. 53. P. 352.
  26. Saccardi L. // Ann. Chim. 1932. V. 22. P. 88.
  27. Kafka S., Aigner R., Kappe T. // J. Heterocycl. Chem. 2006. V. 43. № 4. P. 1105–1109. https://doi.org/10.1002/jhet.5570430444

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© А.А. Вернигора, Р.В. Брунилин, В.В. Бурмистров, А.В. Давиденко, М.Б. Навроцкий, Н.А. Салыкин, В.В. Чернышов, И.А. Новаков, 2023