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Heterocyclization of compounds containing diazo and cyano groups. 3. Two pathways in the cyclization of 2-diazo-2-cyanoacetic acid derivatives under the influence of bases

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

1,2,3-Triazol-5-olates are formed in the reaction of diazomalonodiamide and 2-diazo-2-cyanoacetic acid amide and N-methylamide with sodium ethoxide, triethylamine, and ammonia. The products of the reaction of 2-diazo-2-cyanoacetamide with primary amines are mixtures of 4-cyano-1,2,3-triazol-5-olates and 5-amino-1-alkyl-1,2,3-triazole-4-carboxamides.

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Literature Cited

  1. Yu. M. Shafran, V. A. Bakulev, V. S. Mokrushin, and G. I. Validuda, Khim. Getrotsikl. Soedin., No. 5, 691 (1986).

    Google Scholar 

  2. R. Huisgen, Khim. Geterotsikl. Soedin., No. 5, 579 (1981).

    Google Scholar 

  3. J. T. Witkovsky, R. K. Robins, and F. A. Lehmkuhl, US Patent No. 3948885; Ref. Zh. Khim., 10145P (1977).

  4. A. Dornow and J. Helberg, Chem. Ber., 93, 2001 (1960).

    Google Scholar 

  5. P. Murray-Rust, J. McManus, S, P. Lennon, A. E. A. Porter, and J. A. Rechke, J. Chem. Soc., Perkin Trans. 1, No. 4, 713 (1984).

    Google Scholar 

  6. R. Buchmann, P. Heinstein, and J. Wells, J. Med. Chem., 17, 1168 (1974).

    Google Scholar 

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See [1] for communication 2.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 926–931, July, 1986.

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Shafran, Y.M., Bakulev, V.A., Mokrushin, V.S. et al. Heterocyclization of compounds containing diazo and cyano groups. 3. Two pathways in the cyclization of 2-diazo-2-cyanoacetic acid derivatives under the influence of bases. Chem Heterocycl Compd 22, 740–745 (1986). https://doi.org/10.1007/BF00522732

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  • DOI: https://doi.org/10.1007/BF00522732

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