Generation of oxodiazonium ions 2. Synthesis of benzotetrazine-1,3-dioxides from 2-(tert-butyl-NNO-azoxy)-N-nitroanilines

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• 作者：M. S. Klenov (1)
  V. P. Zelenov (1)
  A. M. Churakov (1) churakov@ioc.ac.ru
  Yu. A. Strelenko (1)
  V. A. Tartakovsky (1)
• 关键词：Key words 1 ; 2 ; 3 ; 4 ; tetrazine ; 1 ; 3 ; dioxides – ; cinnolines – ; azoxy compounds – ; nitramines – ; oxodiazonium cation – ; electrophilic aromatic substitution – ; 1H – ; 13C – ; and 14N NMR spectroscopy
• 刊名：Russian Chemical Bulletin
• 出版年：2011
• 出版时间：October 2011
• 年：2011
• 卷：60
• 期：10
• 页码：2040-2045
• 全文大小：287.5 KB
• 参考文献：1. M. S. Klenov, M. O. Ratnikov, A. M. Churakov, Yu. A. Strelenko, V. A. Tartakovsky, Izv. Akad. Nauk, Ser. Khim., 2011, 523 [Russ. Chem. Bull., Int. Ed., 2011, 60, 536].
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• 作者单位：1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
• ISSN：1573-9171

文摘

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.