Advertisement

Springer Nature is making Coronavirus research free. View research | View latest news | Sign up for updates

Bismalondialdehydverbindungen, 2. Mitt.: Darstellung und Reaktionen von Bipyrazolen und Biisoxazolen

Bis-malondialdehyde compounds, II: Synthesis and reactions of bipyrazoles and biisoxazoles

  • 100 Accesses

  • 10 Citations

Abstract

Starting from 4-ethynyl-4H-pyrane-3,5-dicarbaldehyde (3 a) methane derivatives were obtained with substituents being five membered rings containing N-atoms—such as 4,4′-dipyrazolylketone and 4,4′-dipyrazolyl-4-triazolylmethane. Reactions of the new methane derivatives were studied.

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

Literatur

  1. 1

    1. Mitt.: Mh. Chem.108, 929 (1977).

  2. 2

    W. Dieckmann undL. Platz, Ber. dtsch. chem. Ges.37, 4638 (1904).

  3. 3

    C. Reichardt undK. Halbritter, Angew. Chem.87, 124 (1975).

  4. 4

    J. Elguero, R. Jacquir undD. Tiziane, Bull. Soc. Chim. Fr.1969, 1687.

  5. 5

    H. A. Staab, Chem. Ber.89, 2088 (1967).

  6. 6

    H. A. Staab, Angew. Chem.74, 407 (1962).

  7. 7

    H. A. Staab, Einführung in die theoretische organische Chemie, 4. Aufl., S. 279. Weinheim: Verlag Chemie. 1966.

  8. 8

    M. L. Sherrill undJ. C. Smith, J. Chem. Soc.1937, 1503.

  9. 9

    T. F. Rutledge, Acetylenic Compounds. New York: Reinhold. 1968.

  10. 10

    F. Bohlmann, H. Schönowsky, E. Inhoffen undG. Grau, Chem. Ber.97, 794 (1964).

  11. 11

    G. Eglington undW. McCrae, in: Adv. Org. Chem.4, 225 ff. New York: Interscience. 1963.

  12. 12

    G. Eglington undA. R. Gailbraith, J. Chem. Soc.1959, 889.

  13. 13

    T. L. Jacobs undD. Dankner, J. Org. Chem.22, 1424 (1957).

  14. 14

    U. van Thiel, Diplomarbeit, Univ. München 1966.

  15. 15

    L. O. Carlsson, Acta Chem. Scand.B 29, 325 (1975).

  16. 16

    J. Sandström, Acta Chem. Scand.16, 2395 (1962).

  17. 17

    C. Wijnberger undC. L. Habraken, J. Heterocycl. Chem.6, 545 (1969).

  18. 18

    F. J. Weigert undJ. D. Roberts, J. Amer. Chem. Soc.90, 3543 (1968).

  19. 19

    R. J. Pugmire undD. M. Grant, J. Amer. Chem. Soc.90, 4232 (1968).

  20. 20

    R. G. Rees undM. J. Green, J. Chem. Soc.B. 1968, 387.

  21. 21

    A. Palm undH. Werbin, Canad. J. Chem.31, 1004 (1953).

  22. 22

    S. Califano undW. Lüttke, Z. phys. Chem.5, 240 (1955).

  23. 23

    S. Califano undW. Lüttke, Z. phys. Chem.6, 83 (1956).

  24. 24

    A. Quilico, in: The Chemistry of Heterocyclic Compounds (A. Weissberger, Hrsg.)17, S. 21. New York-London: Interscience. 1962.

  25. 25

    R. Huisgen undW. Mack, Tetrahedron Lett.17, 583 (1961).

  26. 26

    R. Huisgen, M. Seidel, G. Wallbillich undH. Knupfer, Tetrahedron17, 3 (1962).

  27. 27

    R. Huisgen, M. Seidel, J. Sauer, J. W. McFarland undG. Wallbillich, J. Org. Chem.24, 892 (1959).

  28. 28

    R. Huisgen, Angew. Chem.75, 604 (1963).

  29. 29

    A. Quilico, Experientia26, 1169 (1970).

  30. 30

    R. O. Lindsay undC. F. Allen, in: Organic Synthesis, Coll. Vol. III, S. 710. New York: Wiley. 1955.

  31. 31

    I. Ugi, H. Perlinger undL. Behringer, Chem. Ber.91, 2330 (1958).

  32. 32

    R. Huisgen, L. Möbius, G. Müller, H. Stangl, G. Szeimies undJ. McVernon, Chem. Ber.98, 3992 (1965).

  33. 33

    R. Huisgen, Angew. Chem.75, 742 (1963).

  34. 34

    R. Huisgen, J. Org. Chem.41, 403 (1976).

  35. 35

    R. Huisgen, R. Knorr, L. Möbius undG. Szeimies, Chem. Ber.98, 4014 (1965).

  36. 36

    L. Birkhofer undP. Wegner, Chem. Ber.99, 2512 (1966).

  37. 37

    Merckprodukt Nr. 3261.

  38. 38

    K. H. Buechel, W. Draber, R. R. Schmidt, E. Regel undL. Eue (Farbenfabrik Bayer AG), Ger. Offen. 1 940 626 (Cl. A. 01 n), Chem. Abstr.74, 75496 c (1971).

  39. 39

    G. Jäger, K. H. Buechel undH. Karl (Farbenfabrik Bayer AG), Ger. Offen. 1 940 626 (Cl. C. 07 d, A 61 k, A 01 n), Chem. Abstr.74, 112048f (1971).

  40. 40

    W. Draber, K. H. Buechel undH. Karl (Farbenfabrik Bayer AG), Ger. Offen. 1940, 627 (Cl. C. 07 d, A 61 n, A 01 n), Chem. Abstr.74, 125697 s (1971).

  41. 41

    E. M. Van heyningen undH. M. Taylor (Lilly, Eli und Co.), US-Pat. 3 397 273 (Cl. 424-263), Chem. Abstr.69, 86829 m (1968).

  42. 42

    Lilly, Eli und Co., Fr.-Pat. 1 512 567 (Cl. C 07 d, A 01 n), Chem. Abstr.70, 106392 (1969).

  43. 43

    W. Schwab, Diplomarbeit, Univ. München, 1973.

  44. 44

    H. Kessler, A. Moosmayer undA. Rieker, Tetrahedron25, 287 (1969).

  45. 45

    T. V. Protopopova undA. P. Skoldinov, Zhur. Obshchei. Khim.27, 1276 (1957); Chem. Abstr.52, 3815o (1958).

  46. 46

    K. v. Auwers undH. Müller, J. prakt. Chem. [2],137 81 102 (1933).

  47. 47

    L. Claisen, Ber. dtsch. chem. Ges.36, 3664 (1903);59, 144 (1926).

  48. 48

    H. J. Sturm undH. Armbrust, Ann. Chem.729, 139 (1969).

  49. 49

    R. Jacquier, C. Petrus undF. Petrus, Bull. Soc. Chim. Fr.1966, 2971.

  50. 50

    C. R. Hauser undC. E. Cain, J. Org. Chem.23, 1142 (1958).

  51. 51

    S. Trofimenko, J. Org. Chem.29, 3046 (1964).

Download references

Author information

Correspondence to Franz Wille.

Additional information

Mit 2 Abbildungen

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Wille, F., Schwab, W. Bismalondialdehydverbindungen, 2. Mitt.: Darstellung und Reaktionen von Bipyrazolen und Biisoxazolen. Monatshefte für Chemie 109, 337–355 (1978). https://doi.org/10.1007/BF00906352

Download citation