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Synthesis of o-bisazo-1H-pyrazoles and study of their cyclization to give compounds with a 1,2,4-triazine ring

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reactivities of o-hydroxyarylazo-1H-pyrazoles in reactions involving the formation of a 1,2,4-triazine ring in alkaline and acidic media as a function of the character of the substituent in the 4 position of the 1H-pyrazole and the temperature were studied. o-Hydroxyarylazo-1H-pyrazoles and o-hydroxyarylbisazo-1H-pyrazoles, as well as condensed 1,2,4-triazines, were synthesized by diazo coupling of diazotized 5-amino-3-methyl-1R-pyrazoles and o-aminoazobipyrazoles with azo components, viz., 2,3-dihydroxynaphthalene, 1-methyl-3-hydroxyindole, 3-methyl-1-phenyl-5-pyrazolone, and 5-amino-3-methyl-1R-pyrazoles. Azo compounds that undergo ring closure to a triazine ring with the liberation of water when solutions are heated are obtained in the case of 2,3-dihydroxynaphthalene; only azo and o-bisazo compounds were synthesized in the case of 5-aminopyrazoles. An o-bisazo compound that is converted to a triazine when the hydroxy group is replaced by chlorine was isolated in the case of 5-pyrazolone; only a triazine was obtained with 1-methyl-3-hydroxyindole. The compounds obtained were characterized by their IR, UV, PMR, and mass spectra.

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Authors and Affiliations

  1. All-Union Scientific-Research Institute of Chemical Reagents and Ultrapure Chemical Substances, 107258, Moscow

    V. M. Dziomko & B. K. Berestevich

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  1. V. M. Dziomko
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  2. B. K. Berestevich
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 805–812, June, 1979.

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Dziomko, V.M., Berestevich, B.K. Synthesis of o-bisazo-1H-pyrazoles and study of their cyclization to give compounds with a 1,2,4-triazine ring. Chem Heterocycl Compd 15, 657–663 (1979). https://doi.org/10.1007/BF00539504

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  • DOI: https://doi.org/10.1007/BF00539504

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