1384981-49-0Relevant articles and documents
New syntheses of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide
Zelenov,Lobanova,Sysolyatin,Sevodina
, p. 455 - 465 (2013)
New methods were developed for the synthesis of [1,2,5]oxadiazolo[3,4-e][1, 2,3,4]tetrazine 4,6-dioxide from 4-(tert-butyl-NNO-azoxy)-N-nitro-1,2,5- oxadiazol-3-amine or its alkali metal salts and acid anhydrides (or chlorides) in the presence of strong acids. The yield of [1,2,5]oxadiazolo[3,4-e][1,2,3,4] tetrazine 4,6-dioxide in acetic anhydride in the presence of sulfuric acid or sulfuric anhydride at 20 C in 20 min attained 83%. A general mechanism was proposed for the reactions under study. Acetyl group behaved for the first time as departing group in the synthesis 1,2,3,4-tetrazine 1,3-dioxides, and [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide was obtained in 47% yield from N-[4-(acetyl-NNO-azoxy)-1,2,5-oxadiazol-3-yl]acetamide.
Generation of oxodiazonium ions 2.* Synthesis of benzotetrazine-1,3- dioxides from 2-(tert-butyl-NNO-azoxy)-N-nitroanilines
Klenov,Zelenov,Churakov,Strelenko,Tartakovsky
, p. 2040 - 2045 (2012/09/22)
A new method for the synthesis of benzotetrazine-1,3-dioxides was developed, which involves the reaction of 2-(tert-butyl-NNO-azoxy)-N- nitroanilines with the Ac2O/H2SO4 system. This method was also used for the synthesis of [1,2,5]oxadiazolo[3,4-c]cinnoline-5- oxide from 3-nitramino-4-phenylfurazan. The suggested mechanism of these reactions involves the formation of the intermediate oxodiazonium ion, resulting from acetylation of the oxygen atom of the nitramine group, followed by protonation and ionic dissociation. Then the oxodiazonium ion enters the intramolecular reaction with the neighboring tert-butyl-NNO-azoxy or phenyl group to form the corresponding heterocyclic systems.
