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Reaction of 5-phenyltetrazole with α-epoxides

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A mixture of isomerie 1-(hydroxyethyl)- and 2-(hydroxyethyl)tetrazoles with preponderance of the 1,5 isomer was obtained by alkylation of 5-phenyltetrazole with ethylene oxide in an aqueous alcohol medium in the presence of NaOH. 1,3-Bis(5-phenyl-1-tetrazolyl)-2-propanol is formed from 5-phenyltetrazole and epichlorohydrin under the same conditions. The reaction of 5-phenyltetrazole with epichlorohydrin in acetone in the presence of triethylamine gave 1-(2-hydroxy-3-chloropropyl)-5-phenyltetrazole, the dehydrochlorination of which leads to 1-(2,3-epoxypropyl)-5-phenyltetrazole.

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Authors and Affiliations

  1. A. A. Zhdanov Institute of Petrochemical and Coal-Tar Chemical Synthesis, A. A. Zhdanov Irkutsk State University, 664033, Irkutsk

    S. R. Buzilova, N. I. Kuznetsova, V. M. Shul'gina, G. A. Gareev & L. I. Vereshchagin

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  1. S. R. Buzilova
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  2. N. I. Kuznetsova
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  3. V. M. Shul'gina
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  4. G. A. Gareev
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  5. L. I. Vereshchagin
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 119–121, January, 1983.

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Buzilova, S.R., Kuznetsova, N.I., Shul'gina, V.M. et al. Reaction of 5-phenyltetrazole with α-epoxides. Chem Heterocycl Compd 19, 107–109 (1983). https://doi.org/10.1007/BF00512828

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  • DOI: https://doi.org/10.1007/BF00512828

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