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A general route for the synthesis of pyrimido[4′,5′:4,5]thieno[2,3-c]pyridazine derivatives

Eine allgemeine Synthese von Pyrimido[4′,5′:4,5]thieno[2,3-c]pyridazin-Derivaten

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

Summary

A facile synthesis of 8-substituted pyrimido[4′,5′:4,5]thieno[2,3-c]pyridazines (6a–i) has been accomplished. The sequence involves the ring closure of a heterocyclic aminonitrile precursor (3) after reaction with (dichloromethylene)-dimethylammonium chloride.

Zusammenfassung

Es wurde ein einfacher Syntheseweg für 8-substituierte Pyrimido[4′,5′:4,5]thieno-[2,3-c]pyridazine entwickelt. Die Reaktion verläuft über den Ringschluß eines heterocyclischen Aminonitrilvorläufers (3) nach Umsetzung mit Dichlormethylen-dimethylammoniumchlorid.

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References

  1. Janousek Z, Viehe HG (1976) Chemistry of Dichloromethyleniminium salts. In: Böhme H, Viehe HG (eds) Advances in Organic Chemistry, vol 9, Part 1. Wiley, New York, p 343

    Google Scholar 

  2. Viehe HG, Janousek Z (1973) Angew Chem Int Ed12: 806

    Google Scholar 

  3. Viehe HG (1977) Chem Ind 386

  4. Kukhar VP, Pasternak VI (1974) Synthesis 563

  5. Kodel B (1994) J Heterocycl Chem31: 845

    Google Scholar 

  6. Guillot N, Viehe HG, Tinault B, Clerq JP (1990) Tetrahedron46: 3897

    Google Scholar 

  7. Liebscher J (1988) Z Chem28: 291

    Google Scholar 

  8. Brown DJ (1983) Pyrimidines and their Benzo Derivatives. In: Boulton AJ, McKillop A (eds) Katritzky and Rees Comprehensive Heterocyclic Chemistry, vol 3. Pergamon Press, Oxford, p 57

    Google Scholar 

  9. De Clercq E (1986) J Med Chem29: 1561

    Google Scholar 

  10. Baba M, Pauwels R, Herwig P, De Clercq E, Demistev J, Vaudepulfe M (1987) Biochem Biophys Res Communs142: 128

    Google Scholar 

  11. Heilderberg C, Arafield FJ (1963) Cancer Res23: 1226

    Google Scholar 

  12. De Clercq E (1986) Anticancer Res6: 549

    Google Scholar 

  13. Kelley JL, Linn JA, Selway JWT (1989) J Med Chem32: 218

    Google Scholar 

  14. Albert A (1982) Adv Heterocycl Chem32: 1

    Google Scholar 

  15. Heinisch G, Kopelent H (1990) In: Ellis GP and West GB (eds) Progress in Medicinal Chemistry, vol 27. Elsevier, Amsterdam, p 1

    Google Scholar 

  16. Heinisch G, Kopelent H (1992) In: Ellis GP and West GB (eds) Progress in Medicinal Chemistry, vol 29. Elsevier, Amsterdam, p 141

    Google Scholar 

  17. Ellis GP (1991) Synthesis of Fused Heterocycles. In: Taylor EC (ed) The Chemistry of Heterocyclic Compounds, vol 47. Wiley, New York

    Google Scholar 

  18. Cheng CC (1989) In: Ellis GP, West GB (eds) Progress in Medicinal Chemistry, vol 25. Elsevier Amsterdam, p 35 and references therein

    Google Scholar 

  19. Wamhoff H (1985) Adv Heterocycl Chem38: 300

    Google Scholar 

  20. Elnadgi MH, Motaleb RMA, Mustafa M, Zayed MF, Kamel EM (1987) J Heterocycl Chem24: 1677

    Google Scholar 

  21. Zayed SE, Abou Elmaged EI, Metwally SA, Elnadgi MH (1991) Collect Czech Chem Commun56: 2175 and references therein

    Google Scholar 

  22. Charvát T, Potácek M, Marek J (1995) Monatsh Chem126: 333

    Google Scholar 

  23. Peinador C, Veiga MC, Ojea V, Quintela JM (1994) Heterocycles38: 2065

    Google Scholar 

  24. Quintela JM, Peinador C, Moreira MJ (1995) Tetrahedron51: 5901

    Google Scholar 

  25. Deeb A, Said SA, Hamed MM, Yasin F (1990) J Chin Chem Soc37: 287

    Google Scholar 

  26. Kokel B, Menichi G, Hobar-Habart M (1984) Tetrahedron Lett 1557

Download references

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Quintela, J.M., Veiga, M.C., Conde, S. et al. A general route for the synthesis of pyrimido[4′,5′:4,5]thieno[2,3-c]pyridazine derivatives. Monatsh Chem 127, 739–745 (1996). https://doi.org/10.1007/BF00817265

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  • DOI: https://doi.org/10.1007/BF00817265

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