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Benzindoles

II. Synthesis of γ-(4,5-benzindol-3-yl)butyric acid and its derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The synthesis of γ-(4,5-benzindol-3-yl)butyric acid and a number of its derivatives has been effected. It has been shown that the Fischer cyclization of the β-naphthylhydrazones of δ-formylvaleric acid is accompanied by the formation of parasitic compounds identified as esters of ω,ω-di[3-(γ-alkoxycarbonylpropyl)-4,5-benzindol-2-yl] caproic acids. The yield of the latter increases with an increase in the strength of the acid used as the cyclizing agent.

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Literature cited

  1. N. N. Suvorov and V. K. Antonov, Dokl. Akad. Nauk SSSR, 84, 971 (1952).

    Google Scholar 

  2. N. N. Suvorov, V. K. Antonov, and E. M. Rokhlin, Dokl. Akad. Nauk SSSR, 91, 1345 (1953).

    Google Scholar 

  3. N. N. Suvorov, V. P. Mamaev, and L. B. Shagalov, Dokl Akad. Nauk SSSR, 93, 835 (1953).

    Google Scholar 

  4. L. B. Shagalov, N. P. Sorokina, and N. N. Suvorov, ZhOKh, 34, 1592 (1964).

    Google Scholar 

  5. R. Jackson and R. Manske, J. Am. Chem. Soc., 52, 5029 (1930).

    Google Scholar 

  6. V. V. Feofilaktov, ZhOKh, 17, 993 (1947).

    Google Scholar 

  7. V. V. Feofilaktov, and N. K. Semenova, ZhOKh, 23, 644 (1953).

    Google Scholar 

  8. S. Birghero and O. Finsterle, Gazz., 85, 65 (1955); C. A., 50, 4883 (1956).

    Google Scholar 

  9. A. Chalmers and F. Lions, Proc. Roy. Soc. N. S. Wales, 67, 178 (1933); C. A., 28, 765 (1934).

    Google Scholar 

  10. H. Bauer and E. Strauss, Ber., 65, 308 (1932).

    Google Scholar 

  11. E. Shaw and D. Wooley, J. Am. Chem. Soc., 75, 1877 (1953).

    Google Scholar 

  12. W. Noland and D. Robinson, Tetrahedron, 3, 68 (1958).

    Google Scholar 

  13. N. N. Suvorov and V. S. Murasheva, ZhOKh, 30, 3112 (1962).

    Google Scholar 

  14. N. N. Suvorov, V. A. Porotikova, and V. N. Erakasina, KhGS [Chemistry of Heterocyclic Compounds], 6, 24 (1970).

    Google Scholar 

  15. E. Boer, J. Am. Chem. Soc., 64, 1416 (1942).

    Google Scholar 

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Authors and Affiliations

  1. Mendeleev Moscow Chemical and Technological Institute, USSR

    L. B. Shagalov, V. N. Eraksina, K. F. Turchin & N. N. Suvorov

Authors
  1. L. B. Shagalov
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  2. V. N. Eraksina
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  3. K. F. Turchin
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  4. N. N. Suvorov
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Additional information

For Communication I see [14].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 7,pp. 945–950, July, 1970.

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Shagalov, L.B., Eraksina, V.N., Turchin, K.F. et al. Benzindoles. Chem Heterocycl Compd 6, 878–883 (1970). https://doi.org/10.1007/BF00471680

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  • DOI: https://doi.org/10.1007/BF00471680

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