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Reactions with heterocyclic amidines (VI): Synthesis of some new sym. and assym. pyrazolotriazines and pyrazolo[4,5-e]pyrimidine derivatives

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Abstract

Several new pyrazolo[1,5-a]-S-triazine, pyrazolo[4,5-e]pyrimidine, pyrazolo [1,5-a]pyrimidine derivatives were synthesizedvia condensation of 3-antipyrinyl-5-aminopyrazole (2) with β-bifunctional reagents. The azo analogues of pyrazolo[1,5-a] pyrimidines;i.e pyrazolo[5,1-c]-as-triazine and pyrazolo[5,1-c]-as-benzotriazine were synthesized by coupling of diazotized 2 with agents containing active hydrogen.

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Literature Cited

  1. Elagamey, A.A., Sowellim, S.Z.A. and Khodier, M.N.: Reactions with Heterocyclic Amidines (V). Synthesis of Some New Imidazo-[1,2-b]pyrazole, Pyrazolo[5,1-c]-1,2,4-triazine and Pyrazolo-[5,1-c]-1,2,4-triazole Derivatives.Arch. Pharm. Res. 10(1), 14 (1987).

    Article  CAS  Google Scholar 

  2. Archer, S. and Yarinsky, A.: Recent Developments in the Chemotherapy of Schistosomiasis.Prog. Drug. Res. 16, 11 (1972); C.A.78 143580K (1973).

    PubMed  CAS  Google Scholar 

  3. Jaffe, J.J., McCormack, J.J. and Meymarian, E.: Comparative Properties of Schistosomal and Filarial Dihydrofolate Reductases.Nature (London) 230, 408 (1971).

    Article  CAS  Google Scholar 

  4. Suzuki, S. and Marumo, S.: Structures of Tubercidin,J. Antibiot. Ser. A.14, 34 (1961).

    Google Scholar 

  5. Senga, K., Novinson, T., Wilson H.R. and Robins, R.K.:J. Med. Chem. 24, 610 (1981).

    Article  PubMed  CAS  Google Scholar 

  6. Elagamey, A.A., Abdalla, S.O. and Elmoghayar, M.R.H.: α, β-Unsaturated Nitriles in Heterocyclic Synthesis: Synthesis of Some New Pyrazolo[1,5-a]pyrimidine Derivatives.Monatsh. Chem. 115, 1413 (1984).

    Article  CAS  Google Scholar 

  7. Elagamey, A.A., Elmoghayar, M.R.H. and Elnagdi, M. H.: Reactions with Heterocyclic Amidines.Pharmazie,40, 176 (1985).

    CAS  Google Scholar 

  8. Elagamey, A.A., Ghali, E.A., Harb, A.A. and Elnagdi, M.H.: Reactons with 3-Pyrazolin-5-ones: Synthesis of 3,4-dihydropyridone and Pyrano[2,3-c]pyrazole Derivatives.Arch. Pharm. (Weinheim),320 140 (1987).

    Article  CAS  Google Scholar 

  9. Elagamey, A.A., El-Taweel, F.M.A. and Amer, F.A.: Synthesis of Some New Pyrazolo [1,5-a]Pyrimidine and Pyrazolo[1,5-c]-as-triazine Derivatives.Coll. Czech. Chem. Comm. 51, 2193 (1986).

    CAS  Google Scholar 

  10. Elagamey, A.A., El-Taweel, F.M.A. and Amer, F.A.: α,β-Unsaturated Nitriles in heterocyclic Synthesis. II(I): Synthesis of Pyrazolo[3,4-b]pyridine and Pyrazolo[1,5-a]pyrimidine Derivatives of Antipyrine.J. Prakt. Chem. In press.

  11. Stanovnick, B., Tisler, M., Polanc, S. and Grancner, M.: Reduction of Heterocyclic Azides into Amines with Titanium (III) Chloride.J. Heterocyclic Chem. 14, 621 (1977).

    Google Scholar 

  12. Becher, J., Frandsen, E.G., Dreier, C. and Henriksen, L.: Derivatives and Reactions of Glutacondialdehydes (VI); 1-Substituted-3-formyl-2-(1H)-pyridine-thiones.Tetrahedron,33, 341 (1977).

    Article  CAS  Google Scholar 

  13. Elnagdi, M.H., Elmoghayar, M.R.H., Flieta, D.H., Hafez, E. and Fahmy, S.M.: Pyrimidine Derivatives and Related Compounds (4). A route for the Synthesis of Pyrazolo[3,4-e]astriazines, Pyrazolo 3,4-d pyrimidines and Pyrazolo[1,5-c]as triazines.J. Org. Chem. 41, 3781 (1976).

    Article  PubMed  CAS  Google Scholar 

  14. Elagamey, A.A., El-Sakka, I., El-Shahat, Z. and Elnagdi, M.H.: Activated Nitriles in Heterocyclic Amidines: Studies on the Chemistry of Antipyrin-4-ylacetonitrile.Arch. Pharm. (Weinheim) 317, 289 (1984).

    Article  CAS  Google Scholar 

  15. Orgel, L.E., Cottrell, T.L., Dick, W. and Sutton, L.E.: Trans. Faraday Soc., 47, 113 (1951); through Kost. A.N. and Grandberg, I.I., in “Advances in Heterocyclic Chemistry”,Vol. 7, Katritzky, A.R. and Boulton, A.J., Eds., Academic Press, New York, N.Y. p 347–351 (1966).

    Article  CAS  Google Scholar 

  16. Elagamey, A.A., Abou-Elzahab, M.M. and Harb, A.A.: Reactions with Heterocyclic Amidines: Synthesis of Several New Fused Pyrazole Derivatives.J. Chem. Eng. Data, In press.

  17. Reimlinger, H., Overstraeten, A.V. and Viehe, H.G.: 3(5)-Diazopyrazole.Chem. Ber. 94, 1036 (1961).

    Article  CAS  Google Scholar 

  18. Reimlinger, H. and Overstraeten, A.V.: Reactions of 3(5)-Diazopyrazole (II).Chem. Ber. 99, 3350 (1966).

    Article  CAS  Google Scholar 

  19. Ege, G. and Gilbert, K.: Reactions of Diazo Azoles. (3)-[7+2]-and [11+2]-Cycloaddition Reactions of Diazo Azoles with Isocyanates to Azolo[5,1-d]-1,2,3,5-tetrazine-4-one.Tetrahedron Let. 18, 1576 (1979).

    Google Scholar 

  20. Elmoghayar, M.R.H., Abdalla, S.O. and Nasr, M.Y.A.: The Reaction of Isothiocyanates with 2-Cyanoethanoic Acid Hydrazide.J. Heterocyclic Chem. 21, 781 (1984).

    Article  CAS  Google Scholar 

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  1. Chemistry Department, Faculty of Science, Damietta, A.R. Egypt

    Abdel Ghani Ali Elagamey

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  1. Abdel Ghani Ali Elagamey
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Elagamey, A.G.A. Reactions with heterocyclic amidines (VI): Synthesis of some new sym. and assym. pyrazolotriazines and pyrazolo[4,5-e]pyrimidine derivatives. Arch. Pharm. Res. 10, 173–178 (1987). https://doi.org/10.1007/BF02861909

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  • DOI: https://doi.org/10.1007/BF02861909

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