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Über Ringöffnungen einiger Azolo-und Azinoazine

Heterocycles, Pt. 93. ring opening reactions of some azolo-and azinoazines

Heterocyclen, 93. Mitt.

  • Organische Chemie und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

Ring opening reactions of tetrazolo[1.5—a]pyridines, imidazo[1.2—b]pyridazines, s-triazolo[4.3—b]pyridazines and pyrimido[1.2—b]pyridazines are reported. The reaction takes place at the six-membered ring of azoloazines and the formed monocyclic compounds may subsequently isomerize at the double bonds or new cycles may be formed.

Zusammenfassung

Es wird über Ringöffnungen von Tetrazolo[1,5—a]pyridinen, Imidazo[1,2—b]pyridazinen, s-Triazolo[4,3—b]pyridazinen und Pyrimido[1,2—b]pyridazinen berichtet. Die Reaktion verläuft stets am Sechserring der Azoloazine und bei den entstandenen monocyclischen Verbindungen kann nachfolgend einecis—trans-Isomerisierung stattfinden, oder es kommt zu einem neuen Ringschluß.

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Literatur

  1. V. Pirc, B. Stanovnik undM. Tišler, Mh. Chem.102, 837 (1971).

    Google Scholar 

  2. B. Stanovnik undM. Tišler, Chimia25, 272 (1971).

    Google Scholar 

  3. C. Wentrup, Tetrahedron26, 4969 (1970).

    Google Scholar 

  4. J. H. Boyer undH. W. Hyde, J. Org. Chem.25, 458 (1960).

    Google Scholar 

  5. T. Sasaki, K. Kanematsu undM. Murata, Tetrahedron27, 5121 (1971).

    Google Scholar 

  6. J. H. Boyer, D. I. McCane, W. J. McCarville undA. T. Tweedie, J. Amer. Chem. Soc.75, 5298 (1953).

    Google Scholar 

  7. B. Stanovnik undM. Tišler, Tetrahedron25, 3313 (1969).

    Google Scholar 

  8. A. Kovačič, B. Stanovnik undM. Tišler, J. Heterocycl. Chem.5, 351 (1968).

    Google Scholar 

  9. B. Stanovnik, M. Tišler undP. Škufca, J. Org. Chem.33, 2910 (1968).

    Google Scholar 

  10. H. Reimlinger, Chem. Ber.103, 1900 (1970).

    Google Scholar 

  11. J. N. Sheinker, I. J. Postovskii, N. P. Bedniagina, L. B. Seniavina undL. F. Lipatova, Dokl. Akad. Nauk SSSR141, 1388 (1961).

    Google Scholar 

  12. A. J. Boulton undP. B. Ghosh, in: Adv. in Heterocycl. Chem., Vol. 1, s. 1. (A. R. Katritzky, ed.). New York: Academic Press. 1969.

    Google Scholar 

  13. W. Lwowski, Nitrenes, New York: Interscience 1970.

    Google Scholar 

  14. R. Fosse, A. Hieulle undL. W. Bass, C. r. hebdomad. Sé. Acad. Sci.178, 811 (1924).

    Google Scholar 

  15. P. A. Levene undL. W. Bass, J. Biol. Chem.71, 167 (1927).

    Google Scholar 

  16. F. Baron undD. M. Brown, J. Chem. Soc. [London]1955, 2855.

  17. D. H. Hayes undF. Hayes-Baron, J. Chem. Soc. [London]C 1967, 1528.

  18. H. Bredereck, F. Effenberger undW. Resemann, Angew. Chem.74, 253 (1962).

    Google Scholar 

  19. E. C. Taylor, J. Amer. Chem. Soc.74, 1651 (1952).

    Google Scholar 

  20. A. J. Boulton, P. J. Halls undA. R. Katritzky, J. Chem. Soc. [London]B 1970, 636.

  21. A. Pollak, B. Stanovnik undM. Tišler, J. Heterocycl. Chem.5, 513 (1968).

    Google Scholar 

  22. E. C. Taylor undA. J. Crovetti, J. Org. Chem.19, 1633 (1954).

    Google Scholar 

  23. E. Plažek, Rec. trav. chim. Pays-Bas72, 569 (1953).

    Google Scholar 

  24. L. N. Pino undW. S. Zehrung, J. Amer. Chem. Soc.77, 3154 (1955).

    Google Scholar 

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Herrn Prof. Dr.E. Ziegler zum 60. Geburtstag gewidmet.

Synthesen in der Pyridazin-Reihe, 49. Mitt.

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Pollak, A., Polanc, S., Stanovnik, B. et al. Über Ringöffnungen einiger Azolo-und Azinoazine. Monatshefte für Chemie 103, 1591–1603 (1972). https://doi.org/10.1007/BF00904613

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  • DOI: https://doi.org/10.1007/BF00904613

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