An improved synthesis of 3,6‐diamino‐1,2,4,5‐tetrazine. II. From triaminoguanidine and 2,4‐pentanedione

Abstract

A new synthesis for the title compound that gives an 80% overall yield was developed. Treatment of triaminoguanidine monohydrochloride (1) with 2,4‐pentanedione (2) gave 3,6‐bis(3,5‐dimethylpyrazol‐1‐yl)‐1,2‐dihydro‐1,2,4,5‐tetrazine (3) in 80–85% yield. Oxidation of 3 with nitric oxide or nitrogen dioxide to 3,6‐bis(3,5‐dimethyylpyrazol‐1‐yl)‐1,2,4,5‐tetrazine (4) followed by ammonolysis of 4 gave 3,6‐diamino‐1,2,4,5‐tetrazine (5) in guantitatively yields.

New tetrazines substituted by heteroatoms including the first tetrazine based cyclophane: Synthesis and electrochemical properties

“…In addition, several tetrazine derivatives are fluorescent in the visible wavelengths domain, with a maximum emission in the range 550-575 nm [4]. Their chemistry has recently regained much interest [5], due to the new and much easier synthesis of the basic synthon dichloro-s-tetrazine performed by Hiskey et al [6].…”

Nature of weak inter- and intramolecular interactions in crystals 4. Bifurcated N—H...N bond in a crystal of 3-amino-6-(3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine

“…17 Orange monoclinic crystals were grown from a toluene solution, space group P2 1 /c, a = 6.8748 (2) Interactions N-H....N N(5)-H (5N(2)). ..N(1B) (1 -x, -y, -z) 0.129 0.62 0.0676 -0.0121 3.14 N(5)-H (5N(1) …”

Synthesis, characterization and thermal studies on furazan- and tetrazine-based high energy materials

“…3,6-bis(3,5-dimethyl pyrazolyl-1-yl)-1,2-dihydro-1,2,4,5-tetrazine, was brought down to 3 h as against reported [23] 4 h. N,N -bis-(1,2,4,5-tetrazine-3-yl-3,5-dimethylpyrazol)-hydrazine (6) was prepared using quantitative amount of 99% hydrazine hydrate in place of reported [14] anhydrous hydrazine. The IR spectrum of DAAT displayed N-H stretching and deformation vibrations of the amine groups at 3370, 3290 and 1630 cm −1 , respectively.…”