Synthesis of macrolides containing an azine or hydrazide fragment via successive tishchenko disproportionation and [1 + 1]-condensation

  • G. Yu. Ishmuratov
  • G. R. Mingaleeva
  • M. P. Yakovleva
  • R. R. Muslukhov
  • O. O. Shakhanova
  • E. M. Vyrypaev
  • A. G. Tolstikov
Article

Abstract

Eight potentially useful 15-, 17-, 20-, and 22–25-membered macrolides having an azine or hydrazide fragment were synthesized starting from L-menthol, tetrahydropyran, and 4-methyltetrahydropyran via [1 + 1]-condensation of hydrazine hydrate and some dicarboxylic dihydrazides with 7-oxooctyl 7-oxooctanoate, 3-methyl-7-oxooctyl 3-methyl-7-oxooctanoate, and (3R)-3,7-dimethyl-6-oxooctyl (3R)-3,7-dimethyl-6-oxooctanoate obtained by the Tishchenko reaction from 7-oxo-, 3-methyl-7-oxo, and (3R)-3,7-dimethyl-6-oxooctanals, respectively.

Keywords

Azine Trione Macrocyclic Compound Electron Impact Mass Spectrum Tetrahydropyran 

References

  1. 1.
    Ishmuratov, G.Yu., Yakovleva, M.P., Mingaleeva, G.R., Muslukhov, R.R., Ivanov, S.P., Galkin, E.G., Vyrypaev, E.M., and Tolstikov, G.A., Khim. Prirodn. Soedin., 2009, vol. 45, p. 395.Google Scholar
  2. 2.
    Ishmuratov, G.Yu., Mingaleeva, G.R., Yakovleva, M.P., Muslukhov, R.R., Vyrypaev, E.M., Galkin, E.G., and Tolstikov, A.G., Khim. Prirodn. Soedin., 2009, vol. 45, p. 400.Google Scholar
  3. 3.
    Davydova, S.L., Udivitel’nye makrotsikly (Amazing Macrocycles), Leningrad: Khimiya, 1989.Google Scholar
  4. 4.
    Bogatskii, A.V., Mezo-makrogeterotsikly (Izbrannye trudy) [meso-Macroheterocycles (Selected Works)], Kiev: Naukova Dumka, 1986.Google Scholar
  5. 5.
    Strobykina, I.Yu., Garifullin, B.F., Kovylyaeva, G.I., Musin, R.Z., Gubaidullin, A.T., and Kataev, V.E., Russ. J. Gen. Chem., 2007, vol. 77, p. 1066.CrossRefGoogle Scholar
  6. 6.
    Strobykina, I.Yu., Garifullin, B.F., Kovylyaeva, G.I., Kataev, V.E., and Musin, R.Z., Russ. J. Gen. Chem., 2007, vol. 77, p. 1356.CrossRefGoogle Scholar
  7. 7.
    Challis, B.C. and Challis, J.A., Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 2. Translated under the title Obshchaya organicheskaya khimiya, Moscow: Khimiya, 1985, vol. 4, p. 516.Google Scholar
  8. 8.
    Traldi, P., Vettori, U., Podda, G., Maccioni, A., and Corda, L., Org. Mass Spectrom., 1983, vol. 18, p. 69.CrossRefGoogle Scholar
  9. 9.
    Takhistov, V.V. and Ponomarev, D.A., Organicheskaya mass-spektrometriya (Organic Mass Spectrometry), St. Petersburg: VVM, 2005, p. 40.Google Scholar
  10. 10.
    Ishmuratov, G.Yu., Yakovleva, M.P., Botsman, L.P., Ishmuratova, N.M., Muslukhov, R.R., Khambalova, G.V., and Tolstikov, G.A., Khim. Prirodn. Soedin., 2003, vol. 39, p. 28.Google Scholar
  11. 11.
    Ishmuratov, G.Yu., Yakovleva, M.P., Ganieva, V.A., Muslukhov, R.R., and Tolstikov, G.A., Khim. Prirodn. Soedin., 2005, vol. 39, p. 33.Google Scholar
  12. 12.
    Weygand-Hilgetag Organisch-chemische Experimentierkunst, Hilgetag, G. and Martini, A., Eds., Leipzig: Johann Ambrosius Barth, 1964, 3rd ed. Translated under the title Metody eksperimenta v organicheskoi khimii, Moscow: Khimiya, 1968, p. 459.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  • G. Yu. Ishmuratov
    • 1
  • G. R. Mingaleeva
    • 1
  • M. P. Yakovleva
    • 1
  • R. R. Muslukhov
    • 1
  • O. O. Shakhanova
    • 1
  • E. M. Vyrypaev
    • 1
  • A. G. Tolstikov
    • 1
  1. 1.Institute of Organic Chemistry, Ufa Research CenterRussian Academy of SciencesUfaBashkortostan, Russia

Personalised recommendations