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Branched polycyclic tetrazole systems. 1. Synthesis and structure of 2-(5-tetrazolyl)ethyl derivatives of some CH-, OH-, and NH-acids

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Abstract

The cycloaddition of dimethylammonium azide to the nitrile groups of 2-cyanoethyl derivatives of CH-, OH-, and NH-acids leads to open-chain branched structures containing terminal NH-tetrazolyl groups. An x-ray diffraction structural analysis of tris[2-(5-tetrazolyl)ethyl]nitromethane revealed steric access of the equivalent NH-tetrazolyl rings of the branched system. In going from the branched nitrile substrates to the corresponding tetrazoles, the PMR spectra show a breakdown in the resolution of the multiplet components, which had not been observed previously for monocyclic 5-substituted tetrazoles. A dependence was found for the13C NMR chemical shifts on the pKa values, reflecting the NH-acidity of the branched polycyclic tetrazoles in water.

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Authors
  1. V. Yu. Zubarev
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  2. G. V. Gurskaya
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  3. V. E. Zavodnik
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  4. V. A. Ostrovskii
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Dedicated to the memory of I. N. Goncharova.

St. Petersburg State Technological Institute, 198013 St. Petersburg. V. A. Éngel'gart Institute of Molecular Biology, Russian Academy of Sciences, 117984 Moscow. L. Ya. Karpov Physics and Chemistry Research Institute, 103062 Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1494–1501, November, 1997.

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Zubarev, V.Y., Gurskaya, G.V., Zavodnik, V.E. et al. Branched polycyclic tetrazole systems. 1. Synthesis and structure of 2-(5-tetrazolyl)ethyl derivatives of some CH-, OH-, and NH-acids. Chem Heterocycl Compd 33, 1292–1298 (1997). https://doi.org/10.1007/BF02320330

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  • DOI: https://doi.org/10.1007/BF02320330

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