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1,2-Dipyridazinyl-äthen- und-äthan-1,2-diole aus Pyridazin-carbaldehyden

1,2-dipyridazinyl-ethene- and-ethane-1,2-diols from pyridazinecarboxaldehydes. Syntheses and reactions of pyridazine derivatives, VI

Synthesen und Reaktionen von Pyridazinderivaten, 6. Mitt.

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Abstract

Treatment of pyridazine-4-carboxaldehyde with catalytic amounts of KCN results in formation of pyridazine-4-carboxylic acid and two stereoisomeric diols (4,5). The configurations of4 and5 are explained on basis of the1H-NMR-spectra, the mechanism of reaction is discussed. Pyridazine-3-carboxaldehyde (10) reacts with HCN to form the addition product of10-cyanhydrine to10 (11). HCN-elimination from11 yields the enediol12 which by oxygen is oxidized to pyridazine-3-carboxylic acid or its methyl ester.

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Literatur

  1. 2a)

    Zu Pyridin-carbaldehyden vgl.:W. Mathes undW. Sauermilch, Chem. Ber.85, 1008 (1952).

  2. 2b)

    W. Mathes undW. Sauermilch 89, 1515 (1956).

  3. 2c)

    W. Sauermilch undA. Wolf, Arch. Pharmaz.292, 38 (1959).

  4. 3

    Zu Chinolin-carbaldehyden vgl.:A. Phillips, J. Amer. Chem. Soc.68, 2568 (1946).

  5. 4

    G. Heinisch, E. Luszczak undM. Pailer, Mh. Chem.104, 1372 (1973).

  6. 5

    J. Wiemann, G. Dana, Sa-Le-Thi-Thuan undM. Brami, C. r. hebdomad. Sé. Acad. Sci.258, 3724 (1964).

  7. 6

    H. Neudeck undK. Schlögl, Mh. Chem.106, 229 (1975).

  8. 7

    Publikation in Vorbereitung.

  9. 8

    K. Winterfeld undW. Fahlisch, Arch. Pharmaz.304, 248 (1971).

  10. 9

    A. Albert, Ber. dtsch. chem. Ges.49, 1382 (1916).

  11. 10

    F. Zymalkowski undW. Schauer, Arch. Pharmaz.290, 267 (1957).

  12. 11

    E. Lippmann undS. Ungethüm, Z. Chem.13, 343 (1973).

  13. 12

    C. Buehler, Chem. Reviews64, 7 (1964).

  14. 13

    W. Mathes, W. Sauermilch undT. Klein, Chem. Ber.84, 452 (1951).

  15. 14

    W. Leanza, H. Becker undE. Rogers, J. Amer. Chem. Soc.75, 4086 (1953).

  16. 15

    M. Robba, Ann. Chim. [Paris]5, 351 (1960).

  17. 16

    G. Heinisch, Mh. Chem.104, 953 (1973).

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Herrn Univ.-Prof. Dr.M. Pailer mit den besten Wünschen zum 65. Geburtstag gewidmet.

5. Mitt.:G. Heinisch, E. Luszczak undM. Pailer, Mh. Chem.105, 763 (1974).

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Heinisch, G., Luszczak, E. & Mayrhofer, A. 1,2-Dipyridazinyl-äthen- und-äthan-1,2-diole aus Pyridazin-carbaldehyden. Monatshefte für Chemie 107, 799–808 (1976). https://doi.org/10.1007/BF00906787

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