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Benzindoles

17. Vilsmeier reaction in the angular tetrahydrobenzindole series

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The behavior of tetrahydro[4,5]- and tetrahydro[6,7]benzinodoles in the Vilsmeier reaction was investigated. It was established that the steric hindrance created by the cyclohexane ring condensed in the 4 and 5 positions has a substantial effect on the character of the reaction of tetrahydrobenzindoles with various N,N-disubstituted amines. A case of N-acylation in the investigated reactions is described. 3-Formyl-4,5,6,7-tetrahydro[4,5]- and 6,7,8,9-tetrahydro[6,7]-benzindoles were converted to the corresponding tryptamines.

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Authors and Affiliations

  1. Institute of Biophysics of the Ministry of Public Health of the USSR, 123182, Moscow

    L. B. Shagalov, G. M. Ostapchuk, A. D. Zlobina, V. N. Eraksina, T. A. Babushkina, A. M. Vasil'ev & N. N. Suvorov

  2. D. I. Mendeleev Moscow Institute of Chemical Technology, 125047, Moscow

    L. B. Shagalov, G. M. Ostapchuk, A. D. Zlobina, V. N. Eraksina, T. A. Babushkina, A. M. Vasil'ev & N. N. Suvorov

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  1. L. B. Shagalov
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  2. G. M. Ostapchuk
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  3. A. D. Zlobina
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  4. V. N. Eraksina
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  5. T. A. Babushkina
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  6. A. M. Vasil'ev
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  7. N. N. Suvorov
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Additional information

See [1] for communication 16.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 360–365, March, 1979.

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Shagalov, L.B., Ostapchuk, G.M., Zlobina, A.D. et al. Benzindoles. Chem Heterocycl Compd 15, 296–301 (1979). https://doi.org/10.1007/BF00474096

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  • DOI: https://doi.org/10.1007/BF00474096

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