Advertisement

Russian Chemical Bulletin

, Volume 54, Issue 4, pp 992–996 | Cite as

Cross reactions of cyanoacetic acid derivatives with carbonyl compounds 3. One-step synthesis of substituted 2-amino-5-oxo-4,5-dihydropyrano[3,2-c]chromenes

  • A. A. Shestopalov
  • L. A. Rodinovskaya
  • A. M. Shestopalov
  • V. P. Litvinov
Article

Abstract

Three-component reactions of 4-hydroxycoumarin, carbonyl compounds, and malono-nitrile or alkyl cyanoacetates in ethanol in the presence of Et3N as a catalyst give substituted 2-amino-5-oxo-4,5-dihydropyrano[3,2-c]chromenes.

Key words

malononitrile alkyl cyanoacetates 4-hydroxycoumarin 2-amino-5-oxo-4,5-dihydropyrano[3,2-c]chromenes spiro[indoline-3,4′]pyrano[3,2-c]chromenes cross reactions 6-amino-2,1′-bis(benzyloxycarbonyl)-5,7,7-tricyanospiro[3,7,8,8a-tetrahydro-1H-isoquinoline-8,4′-piperidine] 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    A. M. Shestopalov, S. G. Zlotin, A. A. Shestopalov, V. Yu. Mortikov, and L. A. Rodinovskaya, Izv. Akad. Nauk, Ser. Khim., 2004, 546 [Russ. Chem. Bull., Int. Ed., 2004, 53, 573].Google Scholar
  2. 2.
    US Pat. 3 097 213; Ref. Zh., Khim., 1965, 12N257P.Google Scholar
  3. 3.
    Jpn Pat. 12 901; Ref. Zh., Khim., 1968, 12N568P.Google Scholar
  4. 4.
    Yu. A. Sharanin, M. P. Goncharenko, and V. P. Litvinov, Usp. Khim., 1998, 67, 442 [Russ. Chem. Rev., 1998, 67 (Engl. Transl.)].Google Scholar
  5. 5.
    A. M. Shestopalov and Yu. M. Emeliyanova, in Selected Method for Synthesis and Modification of Heterocycles, Ed. V. G. Kartsev, IBS PRESS, Moscow, 2003, 2, 363.Google Scholar
  6. 6.
    The Merck Index, Ed. V. J. O'Neil, Merck and Co., Inc., Whitehouse Station, New York, 2001, 1818.Google Scholar
  7. 7.
    S. M. A. Mousawi, Y. M. Elkholy, M. A. Mohammad, and M. H. Elnagdi, Org. Prep. Proc. Int., 1999, 31, 305.Google Scholar
  8. 8.
    F. Freeman, Chem. Rev., 1980, 80, 329.CrossRefGoogle Scholar
  9. 9.
    A. M. Shestopalov, Z. I. Niazimbetova, D. H. Evans, and M. E. Niyazymbetov, Heterocycles, 1999, 51, 1101.Google Scholar
  10. 10.
    A. M. Shestopalov, Yu. M. Emeliyanova, A. A. Shestopalov, L. A. Rodinovskaya, Z. I. Niazimbetova, and D. H. Evans, Tetrahedron, 2003, 59, 7491.CrossRefGoogle Scholar
  11. 11.
    A. M. Shestopalov, Yu. M. Emeliyanova, and V. N. Nesterov, Izv. Akad. Nauk, Ser. Khim., 2002, 2079 [Russ. Chem. Bull., Int. Ed., 2002, 51, 2238].Google Scholar
  12. 12.
    A. M. Shestopalov and O. A. Naumov, Izv. Akad. Nauk, Ser. Khim., 2003, 1306 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1380].Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • A. A. Shestopalov
    • 1
  • L. A. Rodinovskaya
    • 1
  • A. M. Shestopalov
    • 1
  • V. P. Litvinov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations