Synthesis 2019; 51(06): 1482-1490
DOI: 10.1055/s-0037-1610312
paper
© Georg Thieme Verlag Stuttgart · New York

Convenient Synthesis of Ethyl 5-Oxohomoadamantane-4-carboxylate: A Useful Precursor of Polyfunctional Homoadamantanes

a  Department of Organic Chemistry, Chemical Technological Faculty, Samara State Technical University, 244 Molodogvardeyskaya st., Samara 443100, Russian Federation   Email: orgchem@samgtu.ru
,
Victor B. Rybakov
b  Chemistry Department, Faculty of Chemistry, Moscow State University, 1–3 Leninskie gory, Moscow 119991, Russian Federation
,
Yuri N. Klimochkin*
a  Department of Organic Chemistry, Chemical Technological Faculty, Samara State Technical University, 244 Molodogvardeyskaya st., Samara 443100, Russian Federation   Email: orgchem@samgtu.ru
› Author Affiliations
The research was supported by the Ministry of Education and Science of the Russian Federation within the framework of the Project part of the State Assignment No. 4.6764.2017/BC and Russian Foundation for Basic Research (Project No. 16-43-630823 A).
Further Information

Publication History

Received: 03 September 2018

Accepted after revision: 12 October 2018

Publication Date:
08 November 2018 (eFirst)

Abstract

A facile and convenient synthesis of ethyl 5-oxohomoadamantane-4-carboxylate is reported, and its chemical properties as a cage analogue of acetoacetic ester are investigated. Various derivatives of homoadamantane were synthesized through the reaction of 5-oxohomoadamantane-4-carboxylate with electrophilic agents, binucleophiles, and hydrazoic acid. Some new unusual products were obtained by the reaction of that β-keto ester with nitric acid and nitrosyl chloride. Cage compounds synthesized could be used as precursors for the diverse condensed heterocyclic compounds with potential viral ion channel abrogating activity that possess conformationally rigid lipophilic moieties.

Supporting Information

 
  • References

    • 1a Wanka L, Iqbal K, Schreiner PR. Chem. Rev. 2013; 113: 3516
    • 1b Morozov IS, Ivanova IA, Lukicheva TA. Pharm. Chem. J. 2001; 35: 235
    • 1c Lamoureux G, Artavia G. Curr. Med. Chem. 2010; 17: 2967
    • 1d Gwaltney 2nd SL. Curr. Top. Med. Chem. 2008; 8: 1545
    • 1e Štimac A, Šekutor M, Mlinarić-Majerski K, Frkanec L, Frkanec R. Molecules 2017; 22: 297
    • 1f Luo GF, Xu XD, Zhang J, Yang J, Gong YH, Lei Q, Jia HZ, Li C, Zhuo RX, Zhang XZ. ACS Appl. Mater. Inter. 2012; 4: 5317
    • 1g Spilovska K, Zemek F, Korabecny J, Nepovimova E, Soukup O, Windisch M, Kuca K. Curr. Med. Chem. 2016; 23: 3245
    • 1h Spasov AA, Khamidova TV, Bugaeva LI, Morozov IS. Pharm. Chem. J. 2000; 34: 1
    • 1i Klimochkin YN, Shiryaev VA, Leonova MV. Russ. Chem. Bull. 2015; 64: 1473
    • 1j Shokova ÉA, Kovalev VV. Pharm. Chem. J. 2016; 50: 63
  • 2 Tsuzuki N, Hama T, Kawada M, Hasui A, Konishi R, Shiwa S, Ochi Y, Futaki S, Kitagawa K. J. Pharm. Sci. 1994; 83: 481
    • 3a Jain MK, Wu NY. M, Morgan TK. Jr, Briggs MS, Murray RK. Jr. Chem. Phys. Lipids 1976; 17: 71
    • 3b Cady SD, Wang J, Wu Y, DeGrado WF, Hong M. J. Am. Chem. Soc. 2011; 133: 4274
    • 4a Hu LH, Sim KY. Tetrahedron Lett. 1998; 39: 7999
    • 4b Yang XW, Wang H, Ma WG, Xia F, Xu G. Tetrahedron 2017; 73: 566
    • 4c Novais C, Kato L, Martins FT, Vaz BG, de Oliveira CM. A. Chem. Data Coll. 2017; 9: 24
    • 4d Yang XW, Li MM, Liu X, Ferreira D, Ding Y, Zhang JJ, Xu G. J. Nat. Prod. 2015; 78: 885
    • 5a Aldrich PE, Hermann EC, Meier WE, Paulshock M, Prichard WW, Synder JA, Watts JC. J. Med. Chem. 1971; 14: 535
    • 5b Dzyuba VA, Isaev SD, Isaeva SS, Klimko YE, Leont’eva NA, Neshchadim GN, Yurchenko AG. Pharm Chem. J. 1987; 21: 780
    • 5c Valverde E, Sureda FX, Vázquez S. Bioorg. Med. Chem. 2014; 22: 2678
    • 6a Moiseev IK, Kon’kov SA, Ovchinnikov KA, Kilyaeva NM, Bormasheva KM, Nechaeva ON, Leonova MV, Klimochkin YuN, Balakhinin SM, Bormotov NI, Serova OA. Pharm. Chem. J. 2012; 45: 588
    • 6b Shiryaev VA, Radchenko EV, Palyulin VA, Zefirov NS, Bormotov NI, Serova OA, Shishkina LN, Baimuratov MR, Bormasheva KM, Gruzd YA, Ivleva EA, Leonova MV, Lukashenko AV, Osipov DV, Osyanin VA, Reznikov AN, Shadrikova VA, Sibiryakova AE, Tkachenko IM, Klimochkin YuN. Eur. J. Med. Chem. 2018; 158: 214
    • 6c Wetherill LF, Holmes KK, Verow M, Müller M, Howell G, Fishwick C, Stonehouse N, Foste R, Blair GE, Harris M, Griffin S, Macdonald A. J. Virol. 2012; JVI.06243-1
    • 6d Klimochkin YA, Shiryaev VV, Petrov PV, Radchenko EA, Palyulin VS, Zefirov N. Curr. Comput. Aided. Drug Des. 2016; 12: 154
    • 7a Kljun J, Turel I. Eur. J. Inorg. Chem. 2017; 12: 1655
    • 7b Hilal HS, Ali-Shtayeh MS, Arafat R, Al-Tel T, Voelter W, Barakat A. Eur. J. Med. Chem. 2006; 41: 1017
    • 7c Vitale P, Scilimati A. Cur. Org. Chem. 2013; 17: 1986
    • 7d Kon’kov SA, Moiseev IK, Zemtsova MN, Bormasheva KM. Russ. Chem. Rev. 2014; 83: 377
  • 8 Jukic M, Sterk D, Casar Z. Curr. Org. Synth. 2012; 9: 488
    • 9a Büchner E, Curtius T. Ber. Dtsch. Chem. Ges. 1885; 18: 2371
    • 9b Schlotterbeck F. Ber. Dtsch. Chem. Ges. 1907; 40: 479
    • 9c Schlotterbeck F. Ber. Dtsch. Chem. Ges. 1907; 40: 1826
    • 9d Schlotterbeck F. Ber. Dtsch. Chem. Ges. 1907; 40: 3000
    • 10a Gyarmati ZC, Csomós P, Bernáth G, Valtamo P, Kivelä H, Klika KD, Kalevi P, Kálmán A. J. Hetetrocycl. Chem. 2004; 41: 187
    • 10b Bernáth G, Stajer G, Fülöp F, Sohár P. J. Heterocycl. Chem. 2000; 37: 439
  • 11 Mock WL, Hartman ME. J. Org. Chem. 1977; 42: 459
  • 12 Philip H, Lowery MK, Havel J. Tetrahedron Lett. 1967; 5048
  • 13 Roberts RM, Edwards MB. J. Am. Chem. Soc. 1950; 72: 5537
  • 14 Amyes TL, Richard JP. J. Am. Chem. Soc. 1991; 113: 1867
  • 15 CCDC 1552406 contains the supplementary crystallographic data. The data can be obtained from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures. Molecular structure is shown in the Supporting Information.
  • 16 CCDC 1846052 contains the supplementary crystallographic data. The data can be obtained from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures. Molecular structure is shown in the Supporting Information.
  • 17 Eberson L, Radner F. Acta Chem. Scand. B 1984; 38: 861
  • 18 Li P, Jia X. Synthesis 2018; 50: 711
  • 19 Adam W, Prechtl F. Chem. Ber. 1991; 124: 2369
    • 20a Knyazeva EA, Skomorohov MY, Klimochkin YN. Chem. Heterocycl. Comp. 2011; 46: 1407
    • 20b Knyazeva EA, Skomorokhov MY, Osipov DV, Klimochkin YN. Chem. Heterocycl. Comp. 2013; 48: 1517
  • 21 Peters JA, Remijnse JD, van der Wiele A, Van Bekkum H. Tetrahedron Lett. 1971; 3065