Skip to main content
SpringerLink
Log in

New method for the synthesis of macrocyclic compounds

XV. Alkylation of 2-carbethoxy-α-cyclo-1-thienones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A method was developed for the preparation of macrocyclic 2-alkylcycloalkanones by alkylation of 2-carbethoxy-α-cyclothienones with subsequent desulfurization and ketone cleavage. Only C-alkylation occurs under the described conditions (potassium metal in hexamethylphosphoric triamide, sodium hydride in dioxane).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. S. Z. Taits, O. A. Kalinovskii, V. S. Bogdanov, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., 170 (1972).

  2. H. Hunsdiecker, Ber., 75, 1197 (1942).

    Google Scholar 

  3. A. T. Blomquist, R. W. Holley, and R. D. Spencer, J. Am. Chem. Soc., 70, 34 (1948).

    Google Scholar 

  4. M. Stoll and A. Commarmont, Helv. Chim. Acta., 31, 1435 (1948).

    Google Scholar 

  5. M. Stoll, U. S. Patent No. 2,526,171 (1950); Chem. Abstr., 45, 2502 (1951).

    Google Scholar 

  6. M. S. R. Nair, H. H. Mathur, and S. C. Bhattachariya, J. Chem. Soc., 4154 (1964).

  7. L. Ruzicka, H. Schinz, and W. Pfeiffer, Helv. Chim. Acta, 11, 686 (1928).

    Google Scholar 

  8. M. Stoll, Helv. Chim. Acta, 31, 1082 (1948).

    Google Scholar 

  9. E. Müller and M. Bauer, Ann., 654, 92 (1962).

    Google Scholar 

  10. S. J. Rhoads, J. C. Gilbert, A. W. Decora, T. R. Garland, R. J. Spangler, and M. J. Urbigkit, Tetrahedron, 19, 1625 (1963).

    Google Scholar 

  11. H. Nozaki, T. Mori, and R. Noyori, Tet. Letters, 779 (1967).

  12. G. Ohloff, J. Becker, and K. H. Schulte-Elte, Helv. Chim. Acta, 50, 705 (1967).

    Google Scholar 

  13. S. Z. Taits and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1698 (1960).

  14. Ya. L. Gol'dfarb, S. Z. Taits, and V. N, Bulgakova, Izv. Akad. Nauk SSSR, Ser. Khim., 1299 (1963).

  15. S. Z. Taits and Ya, L. Gol'dfarb, USSR Author's Certificate No. 132,221 (1960); Byul. Izobr., No. 19 (1960).

  16. H. O. House, Modern Synthetic Reactions, Benjamin, New York (1965), p. 170.

    Google Scholar 

  17. Neuere Methoden der Preparativen Organischen Chemie, Vol. 2, Verlag Chemie, Weinheim/Bergstr. (1960), p. 69.

  18. W. B. Renfrow and A. Renfrow, J. Am. Chem. Soc., 68, 1801 (1946).

    Google Scholar 

  19. É. M. Norman, USSR Author's Certificate No. 214,439 (1968); Byul. Izobr., No. 11 (1968).

  20. A. L. Kurts (Kurz), I. P. Beletskaya, and A, Masias (Macias), and O. A. Reutov, Tet., Letters, 3679 (1968).

  21. G. Brieger and W. M. Pelletier, Tet. Letters, 3555 (1965).

  22. W. J. le Noble and H. F. Morris, J. Org. Chem., 34, 1969 (1969).

    Google Scholar 

  23. A. L. Kurts, I. P. Beletskaya, A. Masias, S. S. Yufit, and O. A. Reutov, Zh. Organ. Khim., 4, 1377 (1968).

    Google Scholar 

  24. E. Frankland and B. F. Duppa, Ann., 145, 82 (1868).

    Google Scholar 

  25. M. Stoll Helv. Chim. Acta, 30, 1401 (1947).

    Google Scholar 

  26. C. G. Swain, R. F. Bader, R. M. Esteve, and R. N. Griffin, J. Am. Chem. Soc., 83, 1951 (1961).

    Google Scholar 

  27. S. Z. Taits, O. A. Kalinovskii, V. S. Bogdanov, and Ya. L. Gol'dfarb, Khim, Geterotsikl. Soedin., 1467 (1970).

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    S. Z. Taits, V. N. Bulgakova & Ya. L. Gol'dfarb

Authors
  1. S. Z. Taits
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. N. Bulgakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ya. L. Gol'dfarb
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

See [1] for communication XIV.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 16–21, January, 1973.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Taits, S.Z., Bulgakova, V.N. & Gol'dfarb, Y.L. New method for the synthesis of macrocyclic compounds. Chem Heterocycl Compd 9, 13–17 (1973). https://doi.org/10.1007/BF00476139

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00476139

Keywords

Search

Navigation