Skip to main content
Log in

Acetylenic fragmentation of acyl derivatives of the Fischer base

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Indolenium salts, which readily undergo cleavage in aqueous alkali to give a monosubstituted acetylene and 1,3,3-trimethyl-2-oxindole, are formed when acyl derivatives of the Fischer base are heated with phosphorus oxychloride. Various aryl- and hetarylacetylenes can be conveniently obtained by this method.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

Literature Cited

  1. A. I. Kiprianov and Yu. L. Slonimskii, Zh. Org. Khim., 3, 168 (1967).

    Google Scholar 

  2. P. Burri, Ciba-Geigy Corporation, Ardsley, New York, US Patent No. 4210591, “NKI 260-Indolinospiropyran compounds,” patent applied for on January 21, 1977 and published on July 1, 1980.

  3. L. Brooker and A. Fumia, French Patent No. 1574253; Chem. Abstr., 73, 26632 (1977).

    Google Scholar 

  4. L. I. Kon'kov, N. M. Prizhiyalgovskaya, and N. N. Suvorov, Dokl. Akad. Nauk SSSR, 278, 1130 (1984).

    Google Scholar 

  5. M. Coenen, Angew. Chem., 61, 11 (1949).

    Google Scholar 

  6. M. Coenen, 633, 118 (1960).

  7. D. Lauerer, M. Coenin, M. Pestemer, and G. Sheibe, Z. Phys. Chem., 10, 236 (1957).

    Google Scholar 

  8. C. C. Bond and M. Hooper, J. Chem. Soc., No. 18, 2453 (1969).

    Google Scholar 

  9. M. S. Shvartsberg, A. A. Moroz, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1306 (1971).

    Google Scholar 

  10. L. D. Gavrilov, V. I. Meshcheryakov, and L. I. Vereshchagin, USSR Inventor's Certificate No. 632679; Byull. Izobret., No. 42, 82 (1978).

  11. J. L. Pule, A. A. Chaffer, and J. S. Cantrell, J. Org. Chem., 46, 115 (1981).

    Google Scholar 

  12. E. Bergmann and A. Bondi, Ber., 66, 278 (1933).

    Google Scholar 

  13. S. F. Vasilevskii, M. S. Shvartsberg, and I. L. Kotlyarevskii, USSR Inventor's Certificate No. 943234; Byull. Izobret., No. 26, 117 (1982).

  14. M. S. Shvartsberg, A. N. Kozhevnikova, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1833 (1971).

    Google Scholar 

  15. M. S. Shvartsberg, A. A. Demeneva, R. Z. Sagdeev, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2546 (1969).

    Google Scholar 

  16. M. I. Bardamova, R. N. Myasnikova, and I. L. Kotlyarevskii, Khim. Geterotsikl. Soedin., No. 11, 1457 (1972).

    Google Scholar 

  17. Varian Associates, High-Resolution NMR Spectra Catalog, National Press (1962), p. 599.

  18. P. L. Julian, J. Pikl. and D. Boggess, J. Am. Chem. Soc., 56, 1797 (1934).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedenii, No. 7, pp. 915–918, July, 1987.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Prizhiyalgovskaya, N.M., Kon'kov, L.I., Tarshits, D.L. et al. Acetylenic fragmentation of acyl derivatives of the Fischer base. Chem Heterocycl Compd 23, 751–754 (1987). https://doi.org/10.1007/BF00475641

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00475641

Keywords

Navigation