Syntyhesis of 1,2,4,5‐Tetrazino[1,6‐a: 4,3‐a′]diquinoxaline

Abstract

SummaryA new one-step synthesis of 2(1H)-quinoxalinone oxime (3) from (1,2-benzenediamine (1) and s-trans-chloroethanedial dioxime (2) is described. This oxime is converted into a new heterocyclic compound, 1,2,4,5,-tetrazino[ 1,6-a :4,3-af]diquinoxaline (4), by the template effect of Co(I1) and Ni(I1) ions.Introduction. ~ The aid of metal ions as templates to direct the steric course of condensations for heterocyclic compounds has been reported [ 1-31. A metal ion brings together the reactants by coordination and the reaction takes place in a series of stereochemically controlled steps. The template effect also enables the synthesis of some compounds which are not otherwise accessible. We have investigated the structures and transition metal complexes of diaminoglyoxime and its substituted derivatives [5-121. A completely conjugated 12-membered macrocycle, dibenzo[b,h]-1,4,7,1O-tetraazacyclododecyne, has been obtained by refluxing its octahydrodioxime derivative in dimethyl sulfoxide [ 131.A one-step preparation of 2(1H)-quinoxalinone oxime (3) is described, and a new heterocyclic ring system, 1,2,4,5-tetrazino[ 1,6-a :4,3-a']diquinoxaline, obtained a template reaction was introduced.

Synthesis of Tetrazines from N-Allenylpyrrole-2-carbaldehydes and pH-Controlled Reversible Fragmentation

“…Also, heteroanthracene structures (with six nitrogen atoms) were obtained by dimerization of quinoxalinone oxime under the action of aqueous cobalt(II) chloride. 23 The above examples cover all known assemblies of the substituted tetrazine systems.…”

“…In a recent work, the dimer of N -aminopyridinium salt was isolated and characterized during the synthesis of triazolazines. Also, heteroanthracene structures (with six nitrogen atoms) were obtained by dimerization of quinoxalinone oxime under the action of aqueous cobalt­(II) chloride . The above examples cover all known assemblies of the substituted tetrazine systems.…”