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Synthesis from Undecylenic Acid of Macroheterocycles with Diacylhydrazine and Ester Fragments

  • G. R. Mingaleeva
  • M. P. YakovlevaEmail author
  • G. Yu. Ishmuratov
Article
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A three-step synthesis of potentially biologically active 30- and 32-membered macroheterocycles with esters and acylhydrazines starting from methyl undecylenate was developed based on [1+1]-condensation of intermediate tetraesters, i.e., bis(10′ -methoxy-10′-oxodecyl)- or bis(11′-methoxy-11′ -oxoundecyl)hexanedioate, with hydrazine hydrate. The structures of the synthesized compounds were confirmed using IR and NMR spectroscopy and mass spectrometry.

Keywords

undecylenic acid ozonolysis hydroboration-oxidation [2+1]-condensation [1+1]-condensation macroheterocycles synthesis 

Notes

Acknowledgment

The work was financially supported by RAS program “Basic Principles of Chemistry” on topic No. 8 “Chemo-, regio-, and stereoselective transformations of terpenoids, steroids, and lipids for targeted synthesis of low-molecular-mass bioregulators” (State Reg. No. AAAA-A17-117011910023-2, 2017).

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • G. R. Mingaleeva
    • 1
  • M. P. Yakovleva
    • 1
    Email author
  • G. Yu. Ishmuratov
    • 1
  1. 1.Ufa Institute of Chemistry, Ufa Federal Research CenterRussian Academy of SciencesUfaRussia

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