Adamantoylation of CH-Acids

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Abstract

Acylation reactions of CH-acids have been studied and an efficient approach to the synthesis of (1-adamantyl)methyl ketone directly from 1-adamantylcarbonyl chlorides has been developed. The proposed method includes successive reactions of carboxylic acid chlorides with diethylmalonate in the presence of sodium hydroxide, further hydrolysis of intermediate ketodiesters in an acidic medium, and decarboxylation.

About the authors

Yu. N. Klimochkin

Samara State Technical University

Samara, Russia

I. R. Korzhev

Samara State Technical University

Samara, Russia

E. A. Ivleva

Samara State Technical University

Email: ivleva.ea@samgtu.ru
Samara, Russia

References

  1. Wanka L., Iqbal K., Schreiner P. R. Chem. Rev. 2013, 113, 3516–3604. doi: 10.1021/cr100264t
  2. Štimac A., Šekutor M., Mlinarić-Majerski K., Frkanec L., Frkanec R. Molecules. 2017, 22, 297–310. doi: 10.3390/molecules22020297
  3. 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
  4. Lamoureux G., Artavia G. Curr. Med. Chem. 2010, 17, 2967–2978. doi: 10.2174/092986710792065027
  5. Shokova É.A., Kovalev V.V. Pharm. Chem. J. 2016, 50 (2), 63–75. doi: 10.1007/s11094-016-1400-7
  6. Stockdale T.P., Williams C.M. Chem. Soc. Rev. 2015, 44, 7737–7763. doi: 10.1039/c4cs00477a
  7. Dembitsky V. M., Gloriozova T. A., Poroikov V. V. Biochem. Biophys. Res. Commun. 2020, 529, 1225–1241. doi: 10.1016/j.bbrc.2020.06.123
  8. Klimochkin Y. N., Shiryaev V. A., Leonova M. V. Russ. Chem. Bull. 2015, 64, 1473–1496. doi: 10.1007/s11172-015-1035-y
  9. Shiryaev V.A., Klimochkin Y.N. Chem. Heterocycl. Compd. 2020, 56 (6), 626–635. doi: 10.1007/s10593-020-02712-6
  10. Spasov A.A., Khamidova T.V., Bugaeva L.I., Morozov I.S. Pharm. Chem. J. 2000, 34, 1–7. doi: 10.1007/BF02524549
  11. Geldenhuys W.J., Malan S.F., Bloomquist J.R., Marchand A.P., Van der Schyf C.J. Med. Res. Rev. 2005, 25, 21–48. doi: 10.1002/med.20013
  12. 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
  13. Shiryaev V.A., Skomorohov M.Y., 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
  14. Moiseev I.K., Kon’kov S.A., Ovchinnikov K.A., Kilyaeva N.M., Bormasheva K.M., Nechaeva O.N., Leonova M.V., Klimochkin Yu.N., Balakhnin S.M., Bormotov N.I., Serova O.A., E.F. Belanov. Pharm. Chem. J. 2012, 45 (10), 588–592. doi: 10.1007/s11094-012-0686-3
  15. Voloshchuk O.M., Korotkiy Y.V., Rybalko S.L., Starosila D.B., Shirobokov V.P. Biopolym. Cell. 2017, 33, 453–462. doi: 10.7124/bc.000968
  16. Pardali V., Giannakopoulou E., Konstantinidi A., Kolocouris A., Zoidis G. Croat. Chem. Acta. 2019, 92, 211–218. doi: 10.5562/cca3540
  17. Wang Y., Hu Y., Xu S., Zhang Y., Musharrafieh R., Kin Hau R., Ma C., Wang J. J. Med. Chem. 2018, 61, 1074–1085. doi: 10.1021/acs.jmedchem.7b01536
  18. Li F., Hu Y., Wang Y., Ma C., Wang J. J. Med. Chem. 2017, 60, 1580–1590. doi: 10.1021/acs.jmedchem.6b01852
  19. Li F., Ma C., DeGrado W.F., Wang J. J. Med. Chem. 2016, 59, 1207–1216. doi: 10.1021/acs.jmedchem.5b01910
  20. Hu Y., Wang Y., Li F., Ma C., Wang J. Eur. J. Med. Chem. 2017, 135, 70–76. doi: 10.1016/j.ejmech.2017.04.038
  21. Hu Y., Kin Hau R., Wang Y., Tuohy P., Zhang Y., Xu S., Ma C., Wang J. ACS Med. Chem. Lett. 2018, 9, 1111–1116. doi: 10.1021/acsmedchemlett.8b00336
  22. Cáceres C. J., Hu Y., Cárdenas-García S., Wu X., Tan H., Carnaccini S., Gay L. C., Geiger G., Ma C., Zhang Q.-Y., Rajao D., Perez D. R., Wang J. Emerg. Microb. Infect. 2021, 10 (1), 1832–1848. doi: 10.1080/22221751.2021.1972769
  23. Klimochkin Yu.N., Moiseev I.K., Vladyko G.V., Korobchenko L.V., Boreko E.I. Pharm. Chem. J. 1991, 25, 485–488. doi: 10.1007/BF00772005
  24. Klimochkin Yu.N., Moiseev I.K., Abramov O.V., Vladyko G.V., Korobchenko L.V., Boreko E.I. Pharm. Chem. J. 1991, 25 (7), 489–492. doi: 10.1007/BF00772006
  25. Kon'kov S.A., Moiseev I.K., Zemtsova M.N., Bormasheva K.M. Russ. Chem. Rev. 2014, 83 (5), 377–390. doi: 10.1070/RC2014v083n05ABEH004374
  26. Shokova E.A., Kovalev V.V. Russ. Chem. Rev. 2011, 80 (10), 927–951. doi: 10.1070/RC2011v080n10ABEH004177
  27. Bhattacharyya S. J. Chem. Soc. Perkin Trans. I. 1995, 1845–1847. doi: 10.1039/P19950001845
  28. Kolocouris A., Dimas K., Pannecouque C., Witvrouw M., Foscolos G.B., Stamatiou G., Fytas G., Zoidis G., Kolocouris N., Andrei G., Snoeck R., De Clercq E. Bioorg. Med. Chem. Lett. 2002, 12, 723–727. doi: 10.1016/S0960-894X(01)00838-1
  29. Krylov V.I., Moiseev S.V., Kutin A.A., Sakhno N.G., Gunar O.V., Yashkir V.A., Merkulov V.A. Pharm. Chem. J. 2016, 49 (12), 821–824. doi: 10.1007/s11094-016-1379-0
  30. Zefirov N.A., Mamaeva A.V., Krasnoperova A.I., Evteeva Yu.A., Milaeva E.R., Kuznetsov S.A., Zefirova O.N. Russ. Chem. Bull. 2021, 70 (3), 549–554. doi: 10.1007/s11172-021-3123-5
  31. Guerra W.D., Lucena-Agell D., Hortigueela R., Rossi R.A., Fernando Diaz J., Padron J.M., Barolo S.M. ChemMedChem. 2021. 16 (19), 3003–3016. doi: 10.1002/cmdc.202100383
  32. Beltran-Hortelano I., Atherton R.L., Rubio-Hernandez M., Sanz-Serrano J., Alcolea V., Kelly J.M., Perez-Silanes S., Olmo F. Eur. J. Med. Chem. 2021, 223, 113646. doi: 10.1016/j.ejmech.2021.113646
  33. Kishi A., Kato S., Sakaguchi S., Ishii Y. Chem. Commum. 1999, 15, 1421–1422. doi: 10.1039/A902384D
  34. Tabushi I., Kojo S., Fukunishi K. J. Org. Chem. 1978, 43 (12), 2370–2374. doi: 10.1021/jo00406a014
  35. Stetter H., Rauscher E. Chem. Ber. 1960. 93 (9), 2054–2057. doi: 10.1002/cber.19600930922
  36. Юрченко А.Г., Федоренко Т.В. ЖОрХ. 1987, 23, 875–880.
  37. Vícha R., Potáček M. Tetrahedron. 2005, 61 (1), 83–88. doi: 10.1016/j.tet.2004.10.059
  38. Rakhimov A.I., Cherepanov A.A. Russ. J. Org. Chem. 2001, 37 (5), 745–745. doi: 10.1023/A:1012466910498
  39. Khusnutdinov R.I., Shchadneva N.A., Mukhametshina L.F. Russ. J. Org. Chem. 2010, 46 (6), 820–822. doi: 10.1134/S1070428010060084
  40. Manchand P.S., Cerruti R.J., Martin J.A., Hill C.H., Merrett J.H., Keech E., Belshe R.B., Connell E.V., Sim L.S. J. Med. Chem. 1990, 33, 1992–1995. doi: 10.1021/jm00169a029
  41. Tsubo T., Chen H.-H., Yokomori M., Fukui K., Kikuchi S., Yamada T. Chem. Lett. 2012, 41 (8), 780–782. doi: 10.1246/cl.2012.780
  42. Stulgies B., Prinz P., Magull J., Rauch K., Meindl K., Ruehl S., de Meijere A. Chem. Eur. J. 2005, 11 (1), 308–320. doi: 10.1002/chem.200400723
  43. Siu J. C., Parry J. B., Lin S. J. Am. Chem. Soc. 2019, 141 (7), 2825–2831. doi: 10.1021/jacs.8b13192
  44. Климочкин Ю.Н., Коржев И.Р., Моисеев И.К., Хлебников Д.Ф., Томсонс У.А., Ошис Я.Ф., Тро-фимов В.Е. А.С. 1767836 (1990). СССР. Б.И. 2006. № 36.
  45. Pozdnyakov V.V., Makarova N.V., Moiseev I.K. Russ. J. Org. Chem. 2001, 37 (9), 1228–1231. doi: 10.1023/A:1013154831862
  46. Коньков С.А., Моисеев И.К. Изв. Вузов. Сер. Хим. и хим. технол. 2010, 53 (8), 14–17.

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