Skip to main content
SpringerLink
Log in

Isocamphananaloge mandelsäure

Syntheses in the isocamphane series, XV. The isocamphaneanalogous mandelic acid

Synthesen in der Isocamphanreihe, 15. Mitt.

  • Organic Chemistry and Biochemistry
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

The synthesis of some new potentially, nitrogenefree spasmolytics is described. Formally the benzene nucleus in some mandelic acid esters, known by their mild spasmolytic activity, is substituted for the isocamphane bicyclus by a) SeO2 oxidation of 1-(3,3-Dimethyl-2-exo-norbornyl)-ethanone (5) to the corresponding ketoaldehyde6, b) oxidation of6 to the isocamphane analogous mandelic acid4 and c) esterification of derivatives of4 with isoamylalcohol and benzylalcohol. Attemps to dehydrate the methylester7 to camphenylideneacetic acid methylester (12) by various methods failed, probably because of the ring strain.

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

Literatur

  1. Ariens, E. J., Fortschr. Arzneim.-Forsch.10, 429 (1966); Pure & Appl. Chem.19, 187 (1969).

    Google Scholar 

  2. Kutter, E., Arzneimittelentwicklung, S. 92. Stuttgart: G. Thieme. 1978.

    Google Scholar 

  3. Buchbauer, G., Hana, G. W., Koch, H., Arch. Pharm.311, 24 (1978).

    Google Scholar 

  4. Krieger, H., Arzneim.-Forsch.18, 129, 324, 487 (1968).

    Google Scholar 

  5. Buchbauer, G., Arzneim.-Forsch.29, 1500 (1979).

    Google Scholar 

  6. Erhart, G., Ruschig, H., Arzneimittel, 2. Aufl. Weinheim: Verlag Chemie. 1971.

    Google Scholar 

  7. Macht, D. I., J. Amer. Pharm. Assoc.11, 882, 897 (1922).

    Google Scholar 

  8. Brock, N., Kühas, E., Lorenz, D., Arzneim.-Forsch.2, 165 (1952).

    Google Scholar 

  9. Funcke, A. B. H., Ernsting, M. J. E., Rekker, R. F., Nanta, W. T., Arzneim.-Forsch.3, 503 (1953).

    Google Scholar 

  10. Erhart, G., Ruschig, H., Arzneimittel, 2. Aufl., Bd. 2, S. 64 und 85.

  11. Buchbauer, G., Hana, G. W., Koch, H., Mh. Chem.107, 387 (1976).

    Google Scholar 

  12. Riley, H. L., Morley, J. F., Friend, N. A. C., J. Chem. Soc.1932, 1875.

  13. Rüedi, P., Eugster, C. H., Helv. Chim. Acta60, 1233 (1977).

    Google Scholar 

  14. Kadaba, P. K., Synthesis1971, 316.

  15. Vowinkel, E., Chem. Ber.99, 1479 (1966).

    Google Scholar 

  16. Shaw, J. E., Kunerth, D. C., Sherry, J. J., Tetrahedron Lett.1973, 689.

  17. Pfeffer, P. E., Foglia, T. A., Barr, P. A., Schmeltz, I., Silbert, L. S., Tetrahedron Lett.1972, 4065.

  18. Langlois, G., Ann. Chim. [9]12, 193 (1919).

    Google Scholar 

  19. Langlois, G., Bull. Soc. Chim. Fr.1927, 386.

  20. Hasselstrom, T., Hampton, B. L., J. Amer. Chem. Soc.61, 3445 (1939).

    Google Scholar 

  21. LoCicero, J. C., Johnson, R. T., J. Amer. Chem. Soc.74, 2094 (1952).

    Google Scholar 

  22. Normant, H., Maitte, P., Bull. Soc. Chim. Fr.1956, 1439.

  23. Abraham, A. N., Vilkas, M., Bull. Soc. Chim. Fr.1960, 1450.

  24. Abraham, A. N., Ann. Chim.5, 961 (1960).

    Google Scholar 

  25. Treibs, W., Orttmann, H., Chem. Ber.93, 545 (1960).

    Google Scholar 

  26. Graf, R., Biener, H., Angew. Chem.75, 857 (1963).

    Google Scholar 

  27. Nayak, U. R., Dev, S., Tetrahedron19, 2269 (1963).

    Google Scholar 

  28. Finnegan, R. A., McNees, R. S., J. Org. Chem.29, 3234 (1964).

    Google Scholar 

  29. Vaughan, W. R., Wolinsky, J., Dueltgen, R. R., Grey, S., Seichter, F. S., J. Org. Chem.35, 400 (1970).

    Google Scholar 

  30. Mariani, E., Schenone, P., Farmaco. Ed. Sci.29, 113 (1974).

    Google Scholar 

  31. Gream, G. E., Pincombe, C. F., Austr. J. Chem.27, 543 (1974).

    Google Scholar 

  32. Corey, E. J., Andersen, N. H., Carlson, R. M., Paust, J., Vedejo, E., Vlattas, I., Winter, R. E. K., J. Amer. Chem. Soc.90, 3245 (1968).

    Google Scholar 

  33. Traynelis, V. J., Hergenrother, W. L., Livingston, J. R., Valicenti, J. A., J. Org. Chem.27, 2377 (1962);Traynelis, V. J., Hergenrother, W. L., J. Org. Chem.29, 221 (1964).

    Google Scholar 

  34. Götz, T., Dtsch. Patent 855 248 (1952); Chem. Abstr.48, 11481 (1954).

  35. Walsh, E. N., Toy, A. D. F., Inorg. Synth.7, 69 (1963).

    Google Scholar 

  36. Monson, R. S., Priest, D. N., J. Org. Chem.36, 3826 (1971).

    Google Scholar 

  37. Hutchins, R. O., Hutchins, M. G., Milewski, C. A., J. Org. Chem.37, 4190 (1972).

    Google Scholar 

  38. Hoffmann, R. V., Bishop, R. D., Fitch, P. M., Hardenstein, R., J. Org. Chem.45, 917 (1980).

    Google Scholar 

  39. Brieger, G., Tetrahedron Lett.1963, 1949.

  40. Buchbauer, G., Mh. Chem.109, 289 (1978).

    Google Scholar 

  41. Lee, J. B., Downie, I. M., Tetrahedron23, 359 (1967).

    Google Scholar 

  42. Jefford, Ch. W., Wallace, T. M., Acar, M., J. Org. Chem.42, 1654 (1977).

    Google Scholar 

  43. Corey, E. J., Suggs, J. W., Tetrahedron Lett.1975, 2647.

  44. Buchbauer, G., Tetrahedron Lett.1977, 7.

  45. Rani Bai, P., Ghatge, B. B., Bhattacharyya, S. C., Tetrahedron22, 907 (1966).

    Google Scholar 

  46. Vaughan, W. R., Teegarden, D. M., J. Amer. Chem. Soc.96, 4902 (1974).

    Google Scholar 

  47. Buchbauer, G., in Vorbereitung.

  48. Arrighetti, S., Vajna, E., Cesca, S., Ital. Patent 885 569 (1971); C.A.86, 106 057 g (1977).

Download references

Author information

Authors and Affiliations

  1. Institut für Pharmazeutische Chemie, Universität Wien, A-1090, Wien, Österreich

    Gerhard Buchbauer, Waltraud Pernold, Dorothea Rassl & Brigitte Blach

Authors
  1. Gerhard Buchbauer
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Waltraud Pernold
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Dorothea Rassl
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Brigitte Blach
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Herrn Prof. Dr.M. Pailer mit den besten Wünschen zum 70. Geburtstag gewidmet.

14. Mitt.:Buchbauer, G., Wiedenhorn, M., Mh. Chem.111, 1299 (1980).

Teil der Diplomarbeit vonW. Pernold, Universität Wien 1979.

Teil der Diplomarbeit vonD. Rassl, Universität Wien 1980.

Teil der Diplomarbeit vonB. Blach, Universität Wien 1981.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Buchbauer, G., Pernold, W., Rassl, D. et al. Isocamphananaloge mandelsäure. Monatshefte für Chemie 112, 517–527 (1981). https://doi.org/10.1007/BF00901831

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00901831

Keywords

Search

Navigation