Amino(tert-butyl-NNO-azoxy)furoxans: synthesis, isomerization, and rearrangement of N-acetyl derivatives

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• 作者：V. P. Zelenov ; A. A. Voronin ; A. M. Churakov ; Yu. A. Strelenko…
• 关键词：furoxans ; aminofuroxans ; tert ; butyl ; NNO ; azoxy group ; 1 ; 2 ; 4 ; oxadiazole ; 1 ; 2 ; 3 ; triazole 1 ; oxide ; the Boulton ; Katritzky rearrangement ; isomerization of furoxans ; 14N NMR spectroscopy
• 刊名：Russian Chemical Bulletin
• 出版年：2013
• 出版时间：January 2013
• 年：2013
• 卷：62
• 期：1
• 页码：117-122
• 全文大小：215KB
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• 作者单位：V. P. Zelenov (1)
  A. A. Voronin (1)
  A. M. Churakov (1)
  Yu. A. Strelenko (1)
  M. I. Struchkova (1)
  V. A. Tartakovsky (1)
  
  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
  
• ISSN：1573-9171

文摘

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.