Advances in the chemistry of 1,2,3,4-tetrazines

Abstract

The experimental and theoretical chemistry of 1,2,3,4-tetrazines have been actively studied in the last 20 years. The increasing interest in this class of compounds is due to the fact that the 1,2,3,4-tetrazine ring is a promising building block for the development of energetic and physiologically active compounds. The review considers various types of 1,2,3,4-tetrazines including completely unsaturated nonannulated tetrazines and their <i>N</i>-oxides; nitrogen-substituted tetrazines; annulated tetrazines with a nitrogen atom common to two heterocycles; 1,2,3,4-tetrazine 1,3-dioxides fused to benzene, pyridine, 1,2,3-triazole or 1,2,5-oxadiazole ring; and also 1,2,3,4-tetrazine 1,3-dioxide fused to one more 1,2,3,4-tetrazine 1,3-dioxide ring. Methods of synthesis and reactivity of these compounds, their crystallographic features, spectral characteristics and thermal stability are described. The results of quantum chemical studies for 1,2,3,4-tetrazine derivatives are presented. The prospects of using 1,2,3,4-tetrazines as energetic compounds are discussed.<br> The bibliography includes 189 references.