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Homolytic alkylation of quinaldine and quinoxaline with 18-crown-6

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Homolytic alkylation of protonated quinoxaline with 18-crown-6, initiated by the system pivalic acid-iron(II) sulfate at 20–25‡C, gives (quinoxalin-2-yl)-18-crown-6 in 85% yield. Under analogous conditions, the reaction with quinoline affords two isomers: (quinolin-4-yl)-18-crown-6 and (quinolin-2-yl)-18-crown-6, in yields of 20 and 30% respectively.

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Literature Cited

  1. Yu. B. Zelechonok, V. V. Zorin, S. S. Zlotskii, and D. L. Rakhmankulov, Khim. Geterotsikl. Soedin., No. 9, 1265 (1985).

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  2. W. Burratti, G. P. Gardini, F. Minisci, F. Bertini, R. Galli, and M. Perchinuno, Tetrahedron, 27, 3655 (1971).

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Authors and Affiliations

  1. Ufa Petroleum Institute, 450062, Ufa

    Yu. B. Zelechonok, L. P. Ivanova, V. V. Zorin, S. A. Kotlyar, S. S. Zlotskii & D. L. Rakhmankulov

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  1. Yu. B. Zelechonok
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  2. L. P. Ivanova
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  3. V. V. Zorin
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  4. S. A. Kotlyar
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  5. S. S. Zlotskii
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  6. D. L. Rakhmankulov
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 75–76, January, 1988.

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Zelechonok, Y.B., Ivanova, L.P., Zorin, V.V. et al. Homolytic alkylation of quinaldine and quinoxaline with 18-crown-6. Chem Heterocycl Compd 24, 64–65 (1988). https://doi.org/10.1007/BF00475569

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  • DOI: https://doi.org/10.1007/BF00475569

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