Synthesis and reactions of allylic azides of the adamantane series

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription or Fee Access

Abstract

A mixture of nucleophilic substitution product and isomeric azide resulting from [3,3]-sigmatropic rearrangement was obtained by interaction of allyl bromides of adamantane series with sodium azide. Epoxidation reactions of allylic azides of the adamantane series were investigated. The reduction of the obtained trans -2-(adamantan-1-yl)-3-(azidomethyl)oxirane with lithium alumohydride synthesized ( S *)-(adamantan-1-yl)[( S *)-aziridin-2-yl]methanol which, when heated with hydrochloric acid, gives the product of the aziridine ring opening is (1 S *,2 R *)-1-(adamantan-1-yl)-3-chloro-1-hydroxypropan-2-amino chloride.

About the authors

M. V. Leonova

Samara State Technical University

Email: mvleon@mail.ru

M. R. Baimuratov

Samara State Technical University

Yu. N. Klimochkin

Samara State Technical University

References

  1. Bräse S., Gil C., Knepper K., Zimmermann V. Angew. Chem. Int. Ed. 2005, 44, 5188-5240. doi: 10.1002/anie.200400657
  2. Organic Azides: Syntheses and Applications. Ed. S. Bräse, K. Banert. New York: Wiley. 2010, 536.
  3. Sivaguru P., Ning Y., Bi X. Chem. Rev. 2021, 121, 4253-4307. doi: 10.1021/acs.chemrev.0c01124
  4. Beenhouwer D.O., Rankin J.A., Mellors J.W. Antiviral Res. 1992, 19, 43-54. doi: 10.1016/0166-3542(92)90055-a
  5. Kumar R., Wiebe L.I., Knaus E.E. J. Med. Chem. 1993, 36, 2470-2474. doi: 10.1021/Jm00069A004
  6. Sun, L., Peng, Y., Yu, W., Zhang, Y., Liang, L., Song, C., Hou, J., Qiao, Y., Wang, Q., Chen, J., Wu, M., Zhang, D., Li, E., Han, Z., Zhao, Q., Jin, X., Zhang, B., Huang, Z., Chai, J., Wang, J.-H., Chang, J. J. Med. Chem. 2020, 63, 8554-8566. doi: 10.1021/acs.jmedchem.0c00940
  7. Bhuta, P., Chung, H.L., Hwang, J.-S., Zemlicka, J. J. Med. Chem. 1980, 23, 1299-305. doi: 10.1021/jm00186a004
  8. Gagnon D., Lauzon S., Godbout C., Spino C. Org. Lett. 2005, 7, 4769-4771. doi: 10.1021/ol052034n
  9. Liu R., Gutierrez O., Tantillo D.J., Aube J. J. Am. Chem. Soc. 2012, 134, 6528-6531. doi: 10.1021/ja300369c
  10. Reddy P. S., Ravi V., Sreedhar B. Tetrahedron Lett. 2010, 51, 4037-4041. doi: 10.1016/j.tetlet.2010.05.097
  11. Tjeng A.A., Handore K.L., Batey R.A. Org. Lett. 2020, 22, 3050-3055. doi: 10.1021/acs.orglett.0c00801
  12. Carlson A.S., Topczewski J.J. Org. Biomol. Chem. 2019, 17, 4406-4429. doi: 10.1039/C8OB03178A
  13. Ott A.A., Topczewski J.J. Arkivoc. 2019, i, 1-7. doi: 10.24820/ark.5550190.p010.819
  14. Vallejos M.M., Labadie G.R. RSC Adv. 2020, 10, 4404-4413. doi: 10.1039/c9ra10093h
  15. Gagneux A., Winstein S., Young W.G. J. Am. Chem. Soc. 1960, 82, 5956-5957. doi: 10.1021/ja01507a045
  16. VanderWerf C.A., Heasley V.L. J. Org. Chem. 1966, 31, 3534-3537. doi: 10.1021/jo01349a016
  17. Ott A.A., Packard M.H., Ortuno M.A., Johnson A., Suding V.P., Cramer C.J., Topczewski J.J. J. Org. Chem. 2018, 83. 8214-8224. doi: 10.1021/acs.joc.8b00961
  18. Ott A.A., Topczewski J.J. Org. Lett. 2018, 20, 7253-7256. doi. 10.1021/acs.orglett.8b03168
  19. Feldman A.K., Colasson B., Sharpless K.B., Fokin V.V. J. Am. Chem. Soc. 2005. 127, 13444-13445. doi: 10.1021/ja050622q
  20. Liu R., Zhang Y., Xu J. Chem. Commun. 2021, 57, 8913-8916. doi: 10.1039/d1cc02520a
  21. Vekariya R.H., Liu R., Aubé J. Org. Lett. 2014, 16, 1844-1847. doi: 10.1021/ol500011f
  22. Wanka L., Iqbal K., Schreiner P.R. Chem. Rev. 2013, 113, 3516-3604. doi: 10.1021/cr100264t
  23. 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 Yu.N. Eur. J. Med. Chem. 2021, 221, 113485-113497. doi: 10.1016/j.ejmech.2021.113485
  24. 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
  25. Onajole O.K., Govender P., van Helden P.D., Kruger H.G., Maguire G.E.M., Wiid I., Govender T. Eur. J. Med. Chem. 2010, 45, 2075-2079. doi: 10.1016/j.ejmech.2010.01.046
  26. Augeri D.J., Robl J.A., Betebenner D.A., Magnin D.R., Khanna A., Robertson J.G., Wang A., Simpkins L.M., Taunk P., Huang Q., Han S.-P., Abboa-Offei B., Cap M., Xin L., Tao L., Tozzo E., Welzel G.E., Egan D.M., Marcinkeviciene J., Chang S.Y., Biller S.A., Kirby M.S., Parker R.A., Hamann L.G. J. Med. Chem. 2005, 48, 5025-5037. doi: 10.1021/jm050261p
  27. Duttaroy A., Voelker F., Merriam K., Zhang X., Ren X., Subramanian K., Hughes T.E., Burkey B.F. Eur. J. Pharmacol. 2011, 650, 703-707. doi: 10.1016/j.ejphar.2010.10.062
  28. Леонова М.В., Баймуратов М.Р., Головин Е.В., Климочкин Ю.Н. ЖОрХ. 2014, 50, 194-197.
  29. Leonova M.V., Baimuratov M.R., Golovin E.V., Klimochkin Yu.N. Russ. J. Org. Chem. 2014, 50, 183-186. doi: 10.1134/S1070428014020079
  30. Baimuratov M.R., Leonova M.V., Shiryaev V.A., Klimochkin Y.N. Tetrahedron Lett. 2016, 57, 5317-5320. doi: 10.1016/j.tetlet.2016.10.059
  31. Леонова М.В., Баймуратов М.Р., Климочкин Ю.Н. ЖОрХ. 2014, 50, 1285-1288.
  32. Leonova M.V., Baimuratov M.R., Klimochkin Yu.N. Russ. J. Org. Chem. 2014, 50, 1268-1271. doi: 10.1134/S107042801409005X
  33. Brown H.C., Bartholomay Jr.H., Taylor M.D. J. Am. Chem. Soc. 1944, 66, 435-442. doi: 10.1021/ja01231a039
  34. Tidwell T.T. Tetrahedron. 1978, 34, 1855-1868. doi: 10.1016/0040-4020(78)80089-1
  35. Леонова М.В., Белая Н.В., Баймуратов М.Р., Климочкин Ю.Н. ЖОрХ. 2018, 54, 1634-1641.
  36. Leonova M.V., Belaya N.V., Baimuratov M.R., Klimochkin Y.N. Russ. J. Org. Chem. 2018, 54, 1643-1651. doi: 10.1134/S1070428018110040
  37. Ibuka T. Chem. Soc. Rev. 1998, 27, 145-154. doi: 10.1039/A827145Z
  38. Ibuka T., Nakai K., Habashita H., Hotta Y., Otaka A., Tamamura H., Fujii N., Mimura N., Miwa Y., Chounan Y., Yamamoto Y. J. Org. Chem. 1995, 60, 2044-2058. doi: 10.1021/jo00112a028
  39. Najime R., Pilard S., Vaultier M. Tetrahedron Lett. 1992, 33, 5351-5354. doi: 10.1016/S0040-4039(00)79090-3
  40. Леонова М.В., Пермякова Л.П., Баймуратов М.Р., Климочкин Ю.Н. ЖОрХ. 2020, 56, 591-606.
  41. Leonova M.V., Permyakova L.P., Baimuratov M.R., Klimochkin Yu.N. Russ. J. Org. Chem. 2020, 56, 631-644. doi: 10.31857/S0514749220040114

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2023 Russian Academy of Sciences