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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 2, pp 138–145 | Cite as

Synthesis of new hexahydro-5H-indolo[3,2-c]acridines and indolylbutanoic acids by Fischer cyclization of arylhydrazones

  • Ekaterina V. Zaliznaya
  • Nikolai V. Smetanin
  • Svetlana A. Varenichenko
  • Alexandr V. Mazepa
  • Oleg K. Farat
  • Victor I. Markov
Article
  • 63 Downloads

Arylhydrazones of 2,3,5,6,7,8-hexahydroacridin-4(1H)-ones and 7-amino-6-(arylhydrazono)-7-oxoheptanoic acids were cyclized by Fischer reaction, providing previously unknown polysubstituted indole derivatives. The starting hydrazones were synthesized under Japp–Klingemann reaction conditions by using 1,2,3,4,5,6,7,8-octahydroacridine-4-carboxamide and 2-oxocyclohexanecarboxamide as starting materials. It was established from the spectral data that the obtained 7-amino-6-(arylhydrazono)-7-oxoheptanoic acids existed as mixtures of (Z)- and (E)-isomers, but were converted to an individual (Z)- or (E)-isomer in DMSO solution.

Keywords

diazonium salt octahydroacridines substituted indoles azo coupling electrophilic substitution Fischer reaction Japp–Klingemann reaction 

Notes

The authors would like to express their gratitude to Candidate of Chemical Sciences N. E. Borisova for performing NMR experiments. NMR spectra were acquired at the Laboratory of Magnetic Tomography and Spectroscopy, Department of Chemistry, Moscow State University.

This work received financial support from the Ministry of Education and Science of Ukraine within the framework of the State budget item No. 0115U003159 “New synthetic methods for the design of nitrogen- and sulfur-containing biologically active compounds”.

Supplementary material

10593_2018_2245_MOESM1_ESM.pdf (3.2 mb)
ESM 1 (PDF 3226 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Ekaterina V. Zaliznaya
    • 1
  • Nikolai V. Smetanin
    • 1
  • Svetlana A. Varenichenko
    • 1
  • Alexandr V. Mazepa
    • 2
  • Oleg K. Farat
    • 3
  • Victor I. Markov
    • 1
  1. 1.Ukrainian State University of Chemical TechnologyDniproUkraine
  2. 2.A. V. Bogatsky Physico-Chemical InstituteNational Academy of Sciences of UkraineOdessaUkraine
  3. 3.Lomonosov Moscow State UniversityMoscowRussia

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