New syntheses of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide |
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Authors: | V P Zelenov A A Lobanova S V Sysolyatin N V Sevodina |
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Institution: | 1278. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia 2278. Altay Federal Research and Production Center, Biysk, Altay krai, Russia 3278. Institute for Problems of Chemical and Energetic Technologies, Siberian Branch, Russian Academy of Sciences, Biysk, Altay krai, Russia
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Abstract: | New methods were developed for the synthesis of 1,2,5]oxadiazolo3,4-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]oxadiazolo3,4-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]oxadiazolo3,4-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. |
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