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Activated nitriles in heterocyclic synthesis: Syntheses of thiazole, pyrazole and 4H-1,4-benzothiazine derivatives

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Abstract

4-Arylazo-3-phenyl-5-aminopyrazoles (5a,b) and substituted hydroxythiazoles8a,b were synthesized from the reaction of4a,b with hydrazine hydrate and mercaptoacetic acid respectively. Compounds5a,b and8a,b were also obtained from coupling of2a,b with6 and7, respectively. 4H-1,4-Benzothiazine11 was prepared from1 and10. The reaction of the diazonium salts2a-c with diethyl 3-amino-2-cyanopent-2-en-1,5-dicarboxylate12 was also reported.

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Literature Cited

  1. Godman, L.S. and Gilman, A.G.:The Pharmacological Bases of Therapeutics. Mcmillan Co., London 1177 (1970).

    Google Scholar 

  2. Bayer, A.:Medicinal Chemistry, 2nd ed, 1960, Interscience Publishers, Inc., New York.

    Google Scholar 

  3. Bentley and Driver’s:Textbook of Pharmaceutical Chemistry, 8th ed, London Oxford University, Press, New York, Toronto, 688 (1969).

    Google Scholar 

  4. Tŕefouël, J., Tŕefouël, Mme. J., Nitti, F. and Bovet.: Action of p-aminophenylsulfamide in experimental streptococcus infections of mice and rabbits.Compt. Rend. Soc. Biol. 120, 756 (1935).

    Google Scholar 

  5. Long, H.P. and Bliss, A.E.: p-Aminobenzenesulfonamide and its derivatives. Experimental and clinical observations on their use in the treatment of β-hemolytic streptococci infection.J. Am. Med. Assoc. 108, 32 (1937).

    CAS  Google Scholar 

  6. Northey, E.H.:The Sulphonamides and Allied Compounds. Reinhold, New York (1948).

    Google Scholar 

  7. Burger, A.:Medicinal Chemistry, 3rd ed, part 1, Wiley-Interscience, New York, London, Sydney, Toronto, 255 (1970).

    Google Scholar 

  8. Elnagdi, M.H., Hafez, E.A., El-Fahham, H.A. and Kandeel, E.M.: Reactions with heterocyclic amides (VIII): Synthesis of some new imidazo [1,2-b] pyrazole derivatives.J. Heterocyclic Chem. 17, 73 (1980).

    CAS  Google Scholar 

  9. Elnagdi, M.H., Elmoghayar, M.R.H., Hafez, E.A.A. and Alnima, H.H.: Reaction of 2-arylhydrazono-3-oxonitriles with hydroxylamines: Synthesis of 3-amino-4-arylazoisoxazoles.J. Org. Chem. 40(18), 2604 (1975).

    Article  CAS  Google Scholar 

  10. Elgemeie, G.E.H., Elfahham, H.A., Hassan, E.S.M. and Elnagdi, M.H.: Activated nitriles in heterocyclic synthesis: The reaction of nitriles with mercapto acids.Z. Naturforsch 38b, 781 (1983).

    CAS  Google Scholar 

  11. Elnagdi, M.H., Elfahham, H.A., Ghozlan, S.A.S. and Elgemeie, G.E.H.: Activated nitriles in heterocyclic synthesis: A new procedure for the synthesis of pyrimidine derivatives.J. Chem. Soc. Perkin Trans.I, 2667 (1982).

  12. Shen, T.Y., Clark, R.L., Pessolano, A.A., Witzel, B.E. and Lanza, T.J. (Merck and Co., Inc.) U.S. 4,038,396 (Cl. 424–256; A61K31/44), 26 Jul. (1977),Appl. 574,173,02 May (1975).

  13. Hayakawa, I., Tanaka, Y. and Nagata, Y.: Thiazolopyridine carboxylic acid derivatives (Daiichi Seiyaku Co., Ltd.)Japan. Kokai 7783,588 (Cl. C07D513/04), 12 Jul. (1977),Appl. 76/199, 01 Jan. (1976).

  14. Behr, L.C., Fusco, R. and Jarbe, C.H.: The Chemistry of Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings In Chemistry of Heterocyclic Compounds. Weissberger, Ed. A., Interscience Publishers, New York (1967).

    Google Scholar 

  15. Elnagdi, M.H., Khalifa, M.A.E., Ibraheim, M.K.A. and Elmoghayar, M.R.H.: The reaction of nitriles with mercaptoacetic acid. A new synthesis of thiazole derivatives.J. Heterocyclic Chem.,18, 877 (1981).

    Article  CAS  Google Scholar 

  16. Gupta, R.R. and Gautam, R. K.: Synthesis of 5-substituted 4H-1,4-benzothiazines.Die Pharmazie,3,40,203 (1985).

    Google Scholar 

  17. El-Agamey, 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.Collection Czechoslovak Chem. Commun. 2193, 51 (1986).

    Google Scholar 

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El-Taweel, F.M.AA., Mashaly, M.AH. & Elagamey, A.G.A. Activated nitriles in heterocyclic synthesis: Syntheses of thiazole, pyrazole and 4H-1,4-benzothiazine derivatives. Arch. Pharm. Res. 13, 261–264 (1990). https://doi.org/10.1007/BF02856532

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  • DOI: https://doi.org/10.1007/BF02856532

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