Chemistry of Heterocyclic Compounds

, Volume 15, Issue 6, pp 597–602 | Cite as

Intramolecular cyclization of 2-aryl-3-aminoacetyl-1,4-naphthoquinones to 3-benzocoumaranone derivatives

  • É. Ya. Lokmane
  • L. Ya. Larinya
  • Ya. F. Freimanis
  • I. B. Mazheika
  • É. É. Liepin'sh
Article
  • 24 Downloads

Abstract

The isomerization of 2-aryl-3-(N-alkyl-N-arylamino)acetyl-1,4-naphthoquinones to 2-(N-alkyl-N-arylamino)-4-aryl-5-hydroxy-6,7-benzocoumaran-3-ones was studied. The structures of the compounds obtained were confirmed by the data from the UV, IR, mass and PMR spectra.

Keywords

Organic Chemistry Naphthoquinones Intramolecular Cyclization 

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Literature cited

  1. 1.
    V. T. Glezer, Ya. F. Freimanis, Ya. P. Stradyn', and Ya. Ya. Dregeris, Zh. Obshch. Khim., 49, 1379 (1979).Google Scholar
  2. 2.
    É. Ya. Ozola, Ya. F. Freimanis, and L. Ya. Larinya, Zh. Org. Khim., 11, 1569 (1975).Google Scholar
  3. 3.
    É. Ya. Lokmane, Ya. F. Freimanis, L. Ya. Larinya, L. A. Bitenietse, and I. V. Turovskii, Zh. Org. Khim., 13, 2593 (1977).Google Scholar
  4. 4.
    B. P. Gusev, I. I. Nazarova, and B. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 566 (1966).Google Scholar
  5. 5.
    D. R. Amick, J. Heterocycl. Chem., 12, 1051 (1975).Google Scholar
  6. 6.
    V. A. Gailite, Ya. F. Freimanis, Ya. Ya. Dregeris, É. É. Liepin'sh, and I. B. Mazheika, Zh. Org. Khim., 14, 2118 (1978).Google Scholar
  7. 7.
    A. E. Shvets, Ya. Ya. Bleidelis, Ya. F. Freimanis, and M. F. Bundule, Zh. Strukt. Khim., 18, 107 (1977).Google Scholar
  8. 8.
    M. Fraser, A. Melera, and D. H. Reid, J. Chem. Soc., B, 483 (1966).Google Scholar
  9. 9.
    A. V. El'tsov and Kh. L. Muravich-Aleksandr, Zh. Org. Khim., 1, 1307 (1965).Google Scholar
  10. 10.
    Z. N. Parnes and D. N. Kursanov, Hydride-Transfer Reactions in Organic Chemistry [in Russian], Nauka, Moscow (1969).Google Scholar
  11. 11.
    D. Buckley, S. Dunstan, and H. B. Henbest, J. Chem. Soc., 4880 (1957).Google Scholar
  12. 12.
    A. V. El'tsov and V. S. Kuznetsov, Zh. Org. Khim., 2, 1482 (1966).Google Scholar
  13. 13.
    E. A. Braude, L. M. Jackman, and R. P. Linstead, J. Chem. Soc., 3548 (1954).Google Scholar
  14. 14.
    N. M. Goim, Z. N. Parnes, I. M. Brunovlenskaya, and D. N. Kursanov, Dokl. Akad. Nauk, 196, 1361 (1971).Google Scholar
  15. 15.
    Ya. F. Freimanis, Izv. Akad. Nauk Latv. SSR, No. 7, 71 (1976).Google Scholar
  16. 16.
    A. M. Detsina, V. V. Russkikh, and E. P. Fokin, Zh. Org. Khim., 13, 2398 (1977).Google Scholar
  17. 17.
    K. Chandrasenan and R. H. Thomson, Tetrahedron, 27, 2529 (1971).Google Scholar

Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • É. Ya. Lokmane
    • 1
  • L. Ya. Larinya
    • 1
  • Ya. F. Freimanis
    • 1
  • I. B. Mazheika
    • 1
  • É. É. Liepin'sh
    • 1
  1. 1.Institute of Organic SynthesisAcademy of Sciences of the Latvian SSRRiga

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