Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

4,5-Diacylpyridazine: Synthese und Umsetzung zu 1,4-Diaryl- bzw. 1,4-Dialkyl-pyridazino [4,5—d]pyridazinen 8. Mitt. über pyridazine

4,5-diacylpyridazines: Synthesis and conversion to 1,4-diarylor 1,4-dialkyl-pyridazino[4,5-d]pyridazines(Pyridazines, VIII)


It is found that protonated pyridazine is attacked by nucleophilic acyl radicals not in the positions of lowest electron density (C-3, C-6) but in C-4 and C-5 yielding diacylpyridazines1 a-e. When acyl radicals bearing hydrogen in α-position to the carbonyl group are used, the diacylpyridazines are mainly converted to cyclopenta[d]pyridazines (e.g.2, 3, 4) by intramolecular aldol reactions. Compounds1 a-d are easily converted to 1,4-disubstituted pyridazino[4,5-d]pyridazines by condensation with semicarbazide or hydrazine respectively.

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


  1. 1

    7. Mitt.:G. Heinisch undA. Mayrhofer, Mh. Chem.108, 213 (1977).

  2. 2a)

    T. Caronna, G. Gardini undF. Minisci, Chem. Comm.1969, 201;

  3. 2b)

    T. Caronna, G. Fronza, F. Minisci undO. Porta, J. Chem. Soc., Perkin Trans. II1972, 2035.

  4. 3

    G. Heinisch, A. Jentzsch undM. Pailer, Mh. Chem.105, 648 (1974).

  5. 4

    G. Heinisch und Mitarb. (unveröffentlicht)

  6. 5

    M. Hieda, K. Omura undSh. Yurugi, Yakugaku Zasshi92, 1327 (1972); Chem. Abstr.78, 43402 k;A. Miyake, K. Itoh, N. Tada, Y. Oka undSh. Yurugi, Chem. Pharm. Bull.23, 1488 (1975);M. Tomimoto undSh. Yurugi, Takeda Kenkyusho Ho33, 151 (1974); Chem. Abstr.82, 43325;T. Matsuo undT. Miki, Yakugaku Zasshi92, 703 (1972); Chem. Abstr.77, 88417 g (1972);Y. Oka, K. Itoh, A. Miyake, N. Tada, K. Omura, M. Tomimoto undSh. Yurugi, Chem. Pharm. Bull.23, 2306, 2239 (1975);Sh. Yurugi, T. Fushimi, H. Sugihara undM. Hieda, Yakugaku Zasshi92, 1333 (1972); Chem. Abstr.78, 43400 h;K. Nishikawa, Y. Inada, H. Shimakawa, I. Kuramoto, M. Isono undS. Kikuchi, Takeda Kenkyusho32, 539 (1973); Chem. Abstr.81, 58419.

  7. 6

    Pyridazines (R. Castle, Hrsg.), S. 4. New York: Wiley. 1973.

  8. 7

    F. Minisci, Synthesis1973, 1.

  9. 8

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

  10. 9

    N. Elming, Acta Chem. Scand.6, 572 (1952).

Download references

Author information

Correspondence to Doz. Dr. Gottfried Heinisch.

Additional information

Auszugsweise vorgetragen bei den VÖCh-Chemietagen, Graz, Oktober 1977.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Braun, M., Hanel, G. & Heinisch, G. 4,5-Diacylpyridazine: Synthese und Umsetzung zu 1,4-Diaryl- bzw. 1,4-Dialkyl-pyridazino [4,5—d]pyridazinen 8. Mitt. über pyridazine. Monatshefte für Chemie 109, 63–71 (1978).

Download citation