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

Authors

  • О. А. Шемякина A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Science
  • А. Г. Малькина A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Science
  • А. И. Албанов A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Science
  • Б. А. Трофимов A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Science

DOI:

https://doi.org/10.1007/2074

Keywords:

acetylenic hydroxy nitriles, isomers, tetrazole, nucleophilic addition, regioselectivity

Abstract

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%).

How to Cite
Shemyakina, O. A.; Mal’kina, A. G.; Albanov, A. I.; Trofimov, B. A. Chem. Heterocycl. Compd. 2011, 47(4), 464. [Khim. Geterotsikl. Soedin. 2011, 566.]

For this article in the English edition see DOI 10.1007/s10593-011-0782-4

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Published

2014-11-27

Issue

No. 4 (2011)

Section

Original Papers