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

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 pK_a values, reflecting the NH-acidity of the branched polycyclic tetrazoles in water.

How to Cite
Zubarev, V. Y.; Gurskaya, G. V.; Zavodnik, V. E.; Ostrovskii, V. A. Chem. Heterocycl. Compd. 1997, 33, 1292. [Khim. Geterotsikl. Soedin. 1997, 1494.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02320330