Chemistry of Heterocyclic Compounds

, Volume 5, Issue 2, pp 251–253 | Cite as

Benzindazoles based on triketones of the indan series

I. 5-Hydroxy-1-phenylbenz[g]indazoles
  • E. Ya. Ozola
  • A. K. Aren
  • G. Ya. Vanag


With phenylhydrazine, 2-acetonyl- and 2-phenacyl-2-phenylindan-1,3-diones form phenylhydrazones at the carbonyl group of the side chain. On prolonged heating, a reaction takes place with the expansion of the five-membered ring into a six-membered ring and the formation of the corresponding 5-hydroxy-1-phenylbenz[g]indazoles. A reaction mechanism is proposed. The structure of the compounds obtained has been confirmed by their IR and UV spectra.


Indan Organic Chemistry Carbonyl Reaction Mechanism Carbonyl Group 
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  1. 1.
    C. Bülov and C. Sautermeister, Ber.,39, 647, 1906.Google Scholar
  2. 2.
    A. Smith and H. N. McCoy, Ber.,35, 2169, 1902.Google Scholar
  3. 3.
    C. Paal and E. Dencks, Ber.,36, 491, 1903.Google Scholar
  4. 4.
    M. G. Korschun and C. Roll, Bull. Soc. chim. France, [4]39, 1223, 1926.Google Scholar
  5. 5.
    N. A. Domnin, M. N. Zelenina, and N. S. Glebovskaya, ZhOKh,27, 1516, 1957.Google Scholar
  6. 6.
    Gh. N. Gheorghiu, J. pr. Chem.,146, 193, 1936.Google Scholar
  7. 7.
    E. Ya. Ozola and G. Ya. Vanag, Izv. AN Latv. SSR, ser. khim., 683, 1964.Google Scholar
  8. 8.
    F. M. Beringer and S. A. Galton, J. Org. Chem.,30, 1930, 1965.Google Scholar
  9. 9.
    Gh. Gheorghiu, Bull. Soc. chim. France, [5]6, 493, 1939.Google Scholar
  10. 10.
    E. Ya. Ozola and G. Ya. Vanag, ZhOrKh,3, 2201, 1967.Google Scholar
  11. 11.
    N. H. Cromwell, R. E. Bambury, and R. P. Barkley, J. Am. Chem. Soc.,81, 4294, 1959.Google Scholar
  12. 12.
    N. H. Cromwell and R. E. Bambury, J. Org. Chem.,26, 1729, 1961.Google Scholar
  13. 13.
    R. Huisgen, M. Seidel, G. Wallbillich, and H. Knupfer, Tetrah.,17, 3, 1962.Google Scholar
  14. 14.
    N. S. Vul'fson and R. B. Zhurin, ZhOKh,31, 3381, 1961.Google Scholar
  15. 15.
    N. S. Vul'fson and R. B. Zhurin, ZhOKh,32, 991, 1962.Google Scholar
  16. 16.
    O. Neiland, in the collection: Cyclicβ-Diketones [in Russian], Izd-vo AN Latv. SSR, Riga, p. 41, 1961.Google Scholar
  17. 17.
    G. Ya. Vanag and Ya. Ya. Dregeris, Izv. AN Latv. SSR. ser. khim., 559, 1964.Google Scholar
  18. 18.
    E. M. Danilova and V. V. Perekalin, ZhOrKh,1, 1708, 1965.Google Scholar
  19. 19.
    D. G. O'Sullivan, J. Chem. Soc., 3278, 1960.Google Scholar

Copyright information

© Consultants Bureau 1972

Authors and Affiliations

  • E. Ya. Ozola
    • 1
  • A. K. Aren
    • 1
  • G. Ya. Vanag
    • 1
  1. 1.Institute of Organic Synthesis AS Latvian SSRRiga

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