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Regio- and stereodirection of addition of tetrazole to α,β-acetylenic γ-hydroxy nitrile: synthesis of 1- and 2-(Z)-(2-cyanoethenyl- 1-hydroxyalkyl)tetrazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Using the example of the reaction of tetrazole with 4-hydroxy-4-methyl-2-pentynonitrile, conditions were found under which (Z)-4-hydroxy-4-methyl-3-(1H-tetrazol-1-yl)2-pentenonitrile was formed by regio- and stereoselective addition at atom N(1) of tetrazole (yield 85%, selectivity 95%).

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Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Science, 1 Favorsky St., Irkutsk, 664033, Russia

    O. A. Shemyakina, A. G. Mal’kina, A. I. Albanov & B. A. Trofimov

Authors
  1. O. A. Shemyakina
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  2. A. G. Mal’kina
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  3. A. I. Albanov
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  4. B. A. Trofimov
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Correspondence to B. A. Trofimov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, 566–572, April, 2011.

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Shemyakina, O.A., Mal’kina, A.G., Albanov, A.I. et al. Regio- and stereodirection of addition of tetrazole to α,β-acetylenic γ-hydroxy nitrile: synthesis of 1- and 2-(Z)-(2-cyanoethenyl- 1-hydroxyalkyl)tetrazoles. Chem Heterocycl Comp 47, 464–469 (2011). https://doi.org/10.1007/s10593-011-0782-4

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  • DOI: https://doi.org/10.1007/s10593-011-0782-4

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