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Behavior of N-alkoxybenzimidzoles with respect to nucleophilic reagents. Attempts to synthesize N-hydroxy-2-aminobenzimidazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Various possibilities for the synthesis of N-hydroxy- and N-alkoxy derivatives of 2-aminobenzimidazoles — reductive cyclization of o-nitrophenylureas, the action of sodium amide on 1-alkoxybenzimidazoles, the ammonolysis of 1-alkoxy-2-iodobenzimidazoles, etc. — were investigated. Organometallic compounds of 1-alkoxybenzimidazoles were obtained for the first time, and their reactivities with respect to benzophenone, iodine, and 1-substituted benzimidazoles were studied. 2,2′-Dibenzimidazolyls that contain an alkoxy group in the 1 position were synthesized.

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Literature cited

  1. S. Takahashi and H. Kano, Chem. Pharm. Bull., 11, 1375 (1963).

    Google Scholar 

  2. H. H. Hodgson and E. R. Ward, J. Chem. Soc., 1316 (1949).

  3. A. F. Pozharskii and A. M. Simonov, Chichibabin Amination of Heterocycles [in Russian], Izd. Rostovsk. Univ., Rostov-on-Don (1971).

    Google Scholar 

  4. S. Takahashi and H. Kano, Chem. Pharm. Bull., 12, 282 (1964).

    Google Scholar 

  5. H. Arndt, Ber., 46, 3529 (1913).

    Google Scholar 

  6. C. F. Bryant and H. H. Guy, Chem. Abstr., 52, 12909f (1958).

    Google Scholar 

  7. C. Thate, Rec. Trav. Chim., 48, 115 (1929).

    Google Scholar 

  8. W. Wladkowski, J. Prakt. Chem., 59, 275 (1899).

    Google Scholar 

  9. T. L. Davis and K. C. Blanchardt, Org. Synth., 3, 95 (1923).

    Google Scholar 

  10. W. Gebhardt, Ber., 17, 2088 (1884).

    Google Scholar 

  11. T. L. Davis and K. C. Blanchardt, J. Am. Chem. Soc., 51, 1800 (1929).

    Google Scholar 

  12. B. A. Tertov and S. E. Panchenko, Zh. Obshch. Khim., 33, 3671 (1963).

    Google Scholar 

  13. B. A. Tertov, A. V. Koblik, and Y. V. Kolodyazhnyi (Kolodyazhny), Tetrahedron, Lett., 4445 (1968).

  14. A. F. Wagner, P. E. Wittreich, A. Lusi, and K. Folkes, J. Org. Chem., 27, 3236 (1963).

    Google Scholar 

  15. I. N. Somin, Zh. Obshch. Khim., 39, 1854 (1969).

    Google Scholar 

  16. Y. Tamura, J. Minamikawa, and M. Ikeda, Synthesis, No. 1, 1 (1977).

    Google Scholar 

  17. L. S. éfros, B. A. Porai-Koshits, and S. G. Farbenshtein, Zh. Obshch. Khim., 23, 1694 (1953).

    Google Scholar 

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Authors and Affiliations

  1. Scientific-Research Institute of Physical and Organic Chemistry, Rostov State University, 344006, Rostov-on-Don

    M. M. Medvedeva, A. F. Pozharskii, V. V. Kuz'menko, V. V. Bessonov & B. A. Tertov

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  1. M. M. Medvedeva
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  2. A. F. Pozharskii
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  3. V. V. Kuz'menko
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  4. V. V. Bessonov
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  5. B. A. Tertov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 200–206, February, 1979.

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Medvedeva, M.M., Pozharskii, A.F., Kuz'menko, V.V. et al. Behavior of N-alkoxybenzimidzoles with respect to nucleophilic reagents. Attempts to synthesize N-hydroxy-2-aminobenzimidazoles. Chem Heterocycl Compd 15, 166–172 (1979). https://doi.org/10.1007/BF00480362

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  • DOI: https://doi.org/10.1007/BF00480362

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