Amino(tert-butyl-NNO-azoxy)furoxans: synthesis, isomerization, and rearrangement of N-acetyl derivatives |
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Authors: | V P Zelenov A A Voronin A M Churakov Yu A Strelenko M I Struchkova V A Tartakovsky |
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Institution: | 1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
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Abstract: | 3-Amino-4-(tert-butyl-NNO-azoxy)furoxan (1a) and 4-amino-3-(tert-butyl-NNO-azoxy)-furoxan (1b) and their acetyl derivatives 6a,b were obtained. The equilibria 1a ai 1b and 6a ? 6b were studied. Furoxan 6b can undergo thermal rearrangement into 3-(tert-butyl-NNO-azoxy)(nitro)methyl]-5-methyl-1,2,4-oxadiazole (7), prolonged heating of which gives N-(2-tert-butyl-5-nitro-1-oxido-2H-1,2,3-triazol-4-yl)acetamide (8). With the transformation 7 → 8 as an example, the possibility of participation of the azoxy group in the Boulton-Katritzky rearrangements was demonstrated for the first time. |
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