Chemistry of Heterocyclic Compounds

, Volume 32, Issue 2, pp 158–162 | Cite as

α-Dimethylaminomethylene-γ-thiobutyrolactone and synthesis of heterocyclic derivatives

  • G. P. Tokmakov


By the interaction of γ-thiobutyrolactone with bis(dimethylamino)-tert-butoxymethane, α-dimethylamino-methylene-γ-thiobutyrolactone has been obtained. Its reactions with arylhydrazines have been investigated. With phenylhydrazine, 4-(2-mercaptoethyl)-1 phenylpyrazolone-5 is formed; but with α-substituted phenylhydrazines, as a result of the Fischer reaction and expansion of the thiolactone ring, 9-substituted 4, 9dihydrothiopyrano[3,4-bjindol-1(3H)-ones are formed. Analogous reactions with 1-amino derivatives of tetrahydroquinoline and tetrahydroquinaldine lead to the formation of 5, 6,10,11-tetrahydro-4H, 8H-thiopyruno(4′,3′:4,5jpyrrolo[3,2,1-ijlquinolin-8-ones, representatives of a new heterocyclic system.


Organic Chemistry Dimethylamino Analogous Reaction Phenylhydrazine Heterocyclic System 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    H. Wamhoff and F. Korte, Synthesis, No. 4, 151 (1972).Google Scholar
  2. 2.
    I. I. Grandberg and G. P. Tokmakov, Khim. Geterotsikl. Soedin., No. 8, 1083 (1974).Google Scholar
  3. 3.
    I. I. Grandberg and G. P. Tokmakov, Khim. Geterotsikl. Soedin., No. 2, 207 (1975).Google Scholar
  4. 4.
    I. I. Grandberg and G. P. Tokmakov, Khim. Geterotsikl. Soedin., No. 3, 331 (1980).Google Scholar
  5. 5.
    I. I. Grandberg and G. P. Tokmakov, Khim. Geterotsikl. Soedin., No. 10, 1398 (1988).Google Scholar
  6. 6.
    F. Korte and K. H. Büchel, Chem. Ber.,93, 1021 (1960).Google Scholar
  7. 7.
    G. P. Tokmakov and 1. I. Grandberg, Izv. Timiryazevsk. Skh. Akad., No. 6, 151 (1979).Google Scholar
  8. 8.
    H. Bredereck, G. Simchen, and B. Funke, Chem. Ber.,104, 2709 (1971).Google Scholar
  9. 9.
    G. P. Tokmakov, I. I. Grandberg, and T. G. Zemlyanova, USSR Inventor's Certificate 1,468,902; Byull. Izobret., No. 12 (1989).Google Scholar
  10. 10.
    T. G. Zemlyanova, “Interaction of heterocyclic aldehydes with arylhydrazines: a new direction of the Fischer reaction,” Candidate's Dissertation, Moscow (1986).Google Scholar
  11. 11.
    I. I. Grandberg and T. I. Zuyanova, Khim. Geterotsikl. Soedin., No. 1, 51 (1971).Google Scholar
  12. 12.
    W. Reppe, Justus Liebigs Ann. Chem.,596, 158 (1955).Google Scholar
  13. 13.
    W. E. Truce and D. J. Abraham, J. Org. Chem..28, 964 (1963).Google Scholar
  14. 14.
    H. Bredereck, G. Simchen, S. Rebsdat, W. Kantlehner, P. Horn, and R. Wahe, Chem. Ber.,101, 41 (1968).Google Scholar

Copyright information

© Plenum Publishing Corporation 1996

Authors and Affiliations

  • G. P. Tokmakov
    • 1
  1. 1.K. A. Timiryazev Moscow Agricultural AcademyMoscow

Personalised recommendations