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On the chemistry of pyridazines, XXXVI: Novel diaza-analogs of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

Zur Chemie von Pyridazinen, 36. Mitt.: Neuartige Diazaanaloga des 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ons

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

Abstract

Procedures for the preparation of the novel tricyclic ketones 10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2—d]pyridazin-5-one (3), 5,6-dihydro-11H-benzo[4,5]cyclohepta[2,1—c]pyridazin-11-one (4), and 10,11-dihydro-5H-benzo[4,5]-cyclohepta[1,2—c]pyridazin-5-one (5) starting from a preformed 1,2-diazine system are proposed. The key intermediates7,19, and11 are prepared from (2-phenylethyl)pyridazines6 and18 by introduction of a carboxylic functionality via homolytic alkoxycarbonylation or via a sulfonylReissert-type reaction.

Zusammenfassung

Methoden zur Darstellung der neuen trizyklischen Ketone 10,11-Dihydro-5H-benzo[4,5]cyclohepta[1,2—d]pyridazine-5-on (3), 5,6-Dihydro-11H-benzo[4,5]cyclohepta[2,1—c]pyridazin-11-on (4) und 10,11-Dihydro-5H-benzo[4,5]cyclohepta[1,2—c]pyridazin-5-on (5) ausgehend von einem präformierten 1,2-Diazinsystem werden vorgeschlagen. Die Schlüsselbausteine dieser Synthesen7,19 und11 werden durch Einführung einer Carboxylfunktion in die (2-Phenylethyl)pyridazine6 und18 über homolytische Alkoxycarbonylierung bzw. eine Sulfonyl-Reissert-Reaktion erhalten.

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References

  1. Pyridazines XXXV:Haider N,Heinisch G,Laβnigg D J Heterocycl Chem, in the press

  2. Presented as part of a lecture at the 11th International Congress of Heterocyclic Chemistry, Heidelberg, 1987

  3. Haider N, Heinisch G (1988) J Chem Soc Perkin Trans I: 401

    Google Scholar 

  4. Heinisch G, Laβnigg D (1987) Arch Pharm (Weinheim) 320: 1222

    Google Scholar 

  5. For some representative examples see,Van der Stelt C, Hofman PS, Funcke ABH, Nauta WT (1968) Arzneim Forsch 18: 756;Villani FJ, Daniels PJL, Claire AE, Mann TA, Wang K (1971) J Heterocycl Chem 8: 73;Villani FJ, Wefer EA, Mann TA, Mayer J, Peer L, Levy AS (1972) J Heterocycl Chem 9: 1203;Brenner DG, Halczenko W, Shepard KL (1982) J Heterocycl Chem 19: 897;Halczenko W, Shepard KL (1982) J Heterocycl Chem 19: 967;Brenner DG, Halczenko W, Shepard KL (1985) J Heterocycl Chem 22: 555;Villani FJ, Magatti CV, Vashi DB, Wong J, Popper TL (1986) Arzneim Forsch 36: 1311

    Google Scholar 

  6. Heinisch G, Lötsch G (1985) Tetrahedron 41: 1199

    Google Scholar 

  7. Dostal W, Heinisch G (1986) Heterocycles 24: 793

    Google Scholar 

  8. Dornow A, Abele W (1964) Chem Ber 97: 3349

    Google Scholar 

  9. Laβnigg D (1987) PhD Thesis University of Vienna

  10. Heinisch G, Lötsch G (1985) Angew Chem 97: 694, (1985) Angew Chem Int Ed Engl 24: 692

    Google Scholar 

  11. Heinisch G, Mayrhofer A (1980) Arch Pharm (Weinheim) 313: 53

    Google Scholar 

  12. Heinisch G, Mayrhofer A (1982) Sci Pharm (Wien) 50: 120

    Google Scholar 

  13. Ohsawa A, Uezu T, Igeta H (1978) Chem Pharm Bull 26: 2428

    Google Scholar 

  14. Heinisch G, Mayrhofer A (1977) Monatsh Chem 108: 213

    Google Scholar 

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Authors and Affiliations

  1. Institute of Pharmaceutical Chemistry, University of Vienna, A-1090, Wien, Österreich

    Wolfgang Dostal, Gottfried Heinisch & Gerhard Lötsch

Authors
  1. Wolfgang Dostal
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  2. Gottfried Heinisch
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  3. Gerhard Lötsch
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Dostal, W., Heinisch, G. & Lötsch, G. On the chemistry of pyridazines, XXXVI: Novel diaza-analogs of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one. Monatsh Chem 119, 751–759 (1988). https://doi.org/10.1007/BF00809689

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  • DOI: https://doi.org/10.1007/BF00809689

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