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Synthesis and nitration of NH- and N-vinyl-4,5,7-trimethyl-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It has been shown that the most efficient catalysts for the synthesis of 4,5,7-trimethyl-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridine from 1,2,5-trimethylpyridin-4-one and acetylene under Trofimov conditions are rubidium and potassium hydroxides. Use of Triton B or a mixture of trimethylbenzylammonium chloride with rubidium hydroxide as catalyst gives O-alkylated oxime. Their configurations and conformations were established through separation of the individual isomers of 1-vinyl-4,5,7-trimethyl-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines. Acetyl nitrate nitration of the cis isomer of this compound gave the 2- and 3-nitro derivatives. Similar nitration of 4,5,7-trimethyl-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridine gave the 2-nitro-7-hydroxy derivative.

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Literature Cited

  1. T. N. Borisova, A. V. Varlamov, N. D. Sergeeva, A. T. Soldatenkov, O. V. Zvolinskii, A. A. Astakhov, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 7, 973 (1987).

    Google Scholar 

  2. B. A. Trofimov and A. I. Mikhaleva, N-Vinylpyrroles [in Russian], Khimiya, Novosibirsk (1984), p. 10.

    Google Scholar 

  3. B. A. Trofimov, Heteroatomic Acetylene Derivatives [in Russian], Khimiya, Moscow (1981), p. 164.

    Google Scholar 

  4. I. Zugravescu and M. Petrovanu, N-Ylide Chemistry, Ed. Acad. Republ. Soc. Rom., Bucharest (1974), p. 28.

    Google Scholar 

  5. I. Zugravescu and M. Petrovanu, N-Ylide Chemistry, Ed. Acad. Republ. Soc. Rom., Bucharest (1974), p. 48.

    Google Scholar 

  6. U. Burkert and N. D. Allinger, Molecular Mechanics [Russian translation], Mir, Moscow (1986).

    Google Scholar 

  7. B. A. Trofimov, L. V. Morozova, and A. I. Mikhaleva, Usp. Khim., 54, 1034 (1984).

    Google Scholar 

  8. E. E. Stashenko, P. I. Zakharov, T. N. Borisova, A. V. Varlamov, B. S. Subbotin, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 2, 212 (1988).

    Google Scholar 

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Authors and Affiliations

  1. P. Lumumba University of National Friendship, 117923, Moscow

    T. N. Borisova, I. A. Stazharova, A. É. Aliev, N. S. Prostakov & A. V. Varlamov

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  1. T. N. Borisova
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  2. I. A. Stazharova
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  3. A. É. Aliev
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  4. N. S. Prostakov
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  5. A. V. Varlamov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1375–1380, October, 1991.

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Borisova, T.N., Stazharova, I.A., Aliev, A.É. et al. Synthesis and nitration of NH- and N-vinyl-4,5,7-trimethyl-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines. Chem Heterocycl Compd 27, 1105–1109 (1991). https://doi.org/10.1007/BF00486807

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  • DOI: https://doi.org/10.1007/BF00486807

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