Reactions of 1,3-dihaloadamantanes with nitric acid

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

The reaction of 1,3-dibromoadamantanes with fuming nitric acid gave the mixture of 2-oxaadamantane derivatives. In the same conditions 1,3-diiodoadamantanes gave the corresponding 1,3-dinitroxyadamantanes. A preparative method for the synthesis of 5,7-dimethyl-3-bromomethyl-1-hydroxy-2-oxaadamantan-1-ol from 5,7-dimethyl-1,3-dibromoadamantane was developed. The obtained compounds can be used in the directed synthesis of substances with high molecular complexity for studying of biological activity.

About the authors

E. A Ivleva

Samara State Technical University

Email: ivleva.ea@samgtu.ru

E. V Simatova

Samara State Technical University

Email: ivleva.ea@samgtu.ru

V. V Klepikov

Samara State Technical University

Email: ivleva.ea@samgtu.ru

Yu. E. Khatmullina

Samara State Technical University

Email: ivleva.ea@samgtu.ru

Yu. N. Klimochkin

Samara State Technical University

Email: ivleva.ea@samgtu.ru

References

  1. Stockdale T. P., Williams C. M. Chem. Soc. Rev. 2015, 44, 7737-7763. doi: 10.1039/c4cs00477a
  2. Ширяев В.А., Климочкин Ю.Н. ХГС. 2020, 56, 626-635.
  3. Shiryaev V.A., Klimochkin Y.N. Chem. Heterocycl. Compd. 2020, 56, 626-635. doi: 10.1007/s10593-020-02712-6
  4. Климочкин Ю.Н., Ширяев В.А., Леонова М.В. Изв. АН. Сер. хим. 2015, 64, 1473-1496.
  5. Klimochkin Y.N., Shiryaev V.A., Leonova M.V. Russ. Chem. Bull. 2015, 64, 1473-1496. doi: 10.1007/s11172-015-1035-y
  6. Nasrallah H., Hierso J.-C. Chem. Mater. 2019, 31, 619-642. doi: 10.1021/acs.chemmater.8b04508
  7. Harrison K.W., Rosenkoetter K.E., Harvey B.G. Energy Fuels. 2018, 32, 7786-7791. doi: 10.1021/acs.energyfuels.8b00792
  8. Kovalenko A., Yumusak C., Heinrichova P., Stritesky S., Fekete L., Vala M., Weiter M., Serdar Sariciftci N., Krajcovica J. J. Mater. Chem. C. 2017, 5, 4716-4723. doi: 10.1039/C6TC05076J
  9. 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
  10. Sosonyuk S.E., Peshich A., Tutushkina A.V., Khlevin D.A., Lozinskaya N.A., Gracheva Y.A., Glazunova V.A., Osolodkin D.I., Semenova M.N., Semenov V.V., Palyulin V.A., Proskurnina M.V., Shtila A.A., Zefirov N.S. Org. Biomol. Chem. 2019, 17, 2792-2797. doi: 10.1039/c8ob02915f
  11. Mezeiova E., Korabecny J., Sepsova V., Hrabinova M., Jost P., Muckova L., Kucera T., Dolezal R., Misik J., Spilovska K., Pham N. L., Pokrievkova L., Roh J., Jun D., Soukup O., Kaping D., Kuca K. Molecules. 2017, 22, 1265-1283. doi: 10.3390/molecules22081265
  12. Momose T., Muraoka O. Chem. Pharm. Bull. 1978, 26, 288-295. doi: 10.1248/cpb.26.288
  13. Tsai C.W., Wu K.H., Yang C.C., Wang G.P. React. Funct. Polym. 2015, 91-92, 11-18. doi: 10.1016/j.reactfunctpolym.2015.04.002
  14. Zhu X., Shao B., Vanden Bout D.A., Plunkett K.N. Macromolecules. 2016, 49, 3838-3844. doi: 10.1021/acs.macromol.6b00067
  15. Galukhin A., Nosov R., Taimova G., Nikolaev I., Islamov D., Vyazovkin S. React. Funct. Polym. 2021, 165, 104956. doi: 10.1016/j.reactfunctpolym.2021.104956
  16. Galukhin A., Nosov R., Nikolaev I., Kachmarzhi A., Aleshin R., Islamov D., Vyazovkin S. Thermochim. Acta. 2022, 710, 179177. doi: 10.1016/j.tca.2022.179177
  17. Inomata S., Matsuoka S., Sakai S., Tajima H., Ishizone T. Macromolecules. 2012, 45, 4184-4195. doi: 10.1021/ma300395s
  18. Inomata S., Harada Y., Nakamura Y., Uehara Y., Ishizone T. Polymer Chem. 2013, 51, 4111-4124. doi: 10.1002/pola.26820
  19. Degtyarenko A.S., Handke M., Krдmer K.W., Liu S.-X., Decurtins S., Rusanov E.B., Thompson L.K., Krautscheid H., Domasevitch K.V. Dalton Trans. 2014, 43, 8530-8542. doi: 10.1039/c4dt00174e
  20. Houlihan J.C.C., Moratti S.C., Hanton L.R. Dalton Trans. 2020, 49, 12009-12017. doi: 10.1039/D0DT02437F
  21. Zhang D., Ronson T.K., Güryel S., Thoburn J.D., Wales D.J., Nitschke J.R. J. Am. Chem. Soc. 2019, 141, 14534-14538. doi: 10.1021/jacs.9b07307
  22. Wrona-Piotrowicz A., Makal A., Zakrzewski J. J. Org. Chem. 2020, 85, 11134-11139. doi: 10.1021/acs.joc.0c01060
  23. Шокова Э.А., Ковалев В.В. ЖОрХ. 2021, 57, 994-1005.
  24. Shokova E.A., Kovalev V.V. Russ J. Org. Chem. 2021, 57, 1089-1097. doi: 10.1134/S1070428021070095
  25. Bose S.K., Fucke K., Liu L., Steel P.G., Marder T.B. Angew. Chem. Int. Ed. 2014, 53, 1799-1803. doi: 10.1002/anie.201308855
  26. Bose S.K., Brand S., Omoregie H.O., Haehnel M., Maier J., Bringmann G., Marder T.B. ACS Catal. 2016, 6, 8332-8335. doi: 10.1021/acscatal.6b02918
  27. Wang B., Peng P., Ma W., Liu Z., Huang C., Cao Y., Hu P., Qi X., Lu Q. J. Am. Chem. Soc. 2021, 143, 12985-12991. doi: 10.1021/jacs.1c06473
  28. Mlinarić-Majerski K., Kragol G. Tetrahedron. 2001, 57, 449-457. doi: 10.1016/S0040-4020(00)01013-9
  29. Duddeck H., Elgamal M.H.A., Hanna A.G. Phosphorus Sulfur Relat. Elem. 1986, 28, 307-314.
  30. Тужиков О.И., Малютина И.В., Юрченко Р.И., Кудрявцев А.А. ЖОХ. 1991, 61, 927-928.
  31. Tuzhikov O.I., Malyutina I.V., Yurchenko R.I., Kudryavtsev A.A. J. Gen. Chem. USSR. 1991, 61, 1021-1022.
  32. Pai Y.-M., Wanek E., Weber W. P. J. Organometal. Chem. 1984, 270, 271-276. doi: 10.1016/0022-328X(84)80373-3
  33. Новаков И.А., Орлинсон Б.С., Савельев Е.Н., Потаенкова Е.А., Вострикова О.В., Тараканов Д.П., Наход М.А. ЖОХ. 2017, 87, 1942-1946.
  34. Novakov I.A., Orlinson B.S., Savel'ev E.N., Potaenkova E.A., Vostrikova O.V., Tarakanov D.P., Nakhod M.A. Russ. J. Gen. Chem. 2017, 87, 2762-2765. doi: 10.1134/S1070363217120027
  35. Хуснутдинов Р.И., Щаднева Н.А., Маякова Ю.Ю. ЖОрХ. 2018, 54, 1710-1712.
  36. Khusnutdinov R.I., Shchadneva N.A., Mayakova Y.Y. Russ. J. Org. Chem. 2018, 54, 1728-1730. doi: 10.1134/S1070428018110180
  37. Хуснутдинов Р.И., Щаднева Н.А., Мухаметшина Л.Ф., Джемилев У.М. ЖОрХ. 2009, 45, 1152-1156.
  38. Khusnutdinov R.I., Shchadneva N.A., Mukhametshina L.F., Dzhemilev U. M. Russ. J. Org. Chem. 2009, 45, 1137-1142. doi: 10.1134/S1070428009080041
  39. Ioannou S., Nicolaides A.V. Tetrahedron Lett. 2009, 50, 6938-6940. doi: 10.1016/j.tetlet.2009.08.108
  40. Скоморохов М.Ю, Климочкин Ю.Н. ЖОрХ. 2011, 47, 1775-1779.
  41. Skomorokhov M.Yu., Klimochkin Yu.N. Russ. J. Org. Chem. 2011, 47, 1811-1816. doi: 10.1134/S1070428011120062
  42. Denmark S.E., Henke B.R. J. Am. Chem. Soc. 1991, 113, 2177-2194. doi: 10.1021/ja00006a042
  43. Скоморохов М.Ю, Климочкин Ю.Н. ЖОрХ. 2001, 37, 1096-1097.
  44. Skomorokhov M.Yu., Klimochkin Yu.N. Russ. J. Org. Chem. 2001, 37, 1050-1051. doi: 10.1023/A:1012403322523
  45. Matsuoka S., Ogiwara N., Ishizone T. J. Am. Chem. Soc. 2006, 128, 8708-8709. doi: 10.1021/ja062157i
  46. Mueller A.M., Chen P. J. Org. Chem. 1998, 63, 4581-4586. doi: 10.1021/jo971814+
  47. Inomata S., Harada Y., Nakamura Y., Nakamura T., Ishizone T. Synthesis. 2013, 45, 3332-3340. doi: 10.1055/s-0033-1338554
  48. Lukach A.E., Santiago A.N., Rossi R.A. J. Phys. Org. Chem. 1994, 7, 610-614. doi: 10.1002/poc.610071104
  49. Kawamoto T., Fukuyama T., Ryu I. J. Am. Chem. Soc. 2012, 134, 875-877. doi: 10.1021/ja210585n
  50. Adcock W., Clark C.I. J. Org. Chem. 1993, 58, 7341-7349. doi: 10.1021/jo00078a009
  51. Argueello J.E., Penenory A.B. J. Org. Chem. 2003, 68, 2362-2368. doi: 10.1021/jo026518y
  52. Ghorai S.K., Jin M., Hatakeyama T., Nakamura M. Org. Lett. 2012, 14, 1066-1069. doi: 10.1021/ol2031729
  53. Jirgensons A., Kauss V., Mishnev A.F., Kalvinsh I. J. Chem. Soc., Perkin Trans. 1. 1999, 3527-3530. doi: 10.1039/A904394B
  54. Климочкин Ю.Н., Ивлева Е.А., Моисеев И.К. ЖОрХ. 2020, 56, 1353-1362.
  55. Klimochkin Yu.N., Ivleva E.A., Moiseev I.K. Russ. J. Org. Chem. 2020, 56, 1532-1539. doi: 10.1134/S1070428020090055
  56. Климочкин Ю.Н., Ивлева Е.А., Скоморохов М.Ю. ЖОрХ. 2020, 56, 1344-1352.
  57. Klimochkin Yu.N., Ivleva E.A., Skomorokhov M.Yu. Russ. J. Org. Chem. 2020, 56, 1525-1531. doi: 10.1134/S1070428020090043
  58. Ивлева Е.А., Клепиков В.В., Хатмуллина Ю.Э., Рыбаков В.Б., Климочкин Ю.Н. ЖОрХ. 2022, 58, 51-60.
  59. 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
  60. Molle G., Dubois J.E., Bauer P. Can. J. Chem. 1987, 65, 2428-2433. doi: 10.1139/v87-405
  61. Pincock R.E., Schmidt J., Scott W.B., Torupka E.J. Can. J. Chem. 1972, 50, 3958-3964. doi: 10.1139/v72-627
  62. Моисеев И.К., Климочкин Ю.Н., Земцова М.Н., Трахтенберг П.Л. ЖОрХ. 1984, 20, 1435-1438.
  63. 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.
  64. 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

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2023 Russian Academy of Sciences