Generation of oxodiazonium ions 3. Synthesis of [1,2,5]oxadiazolo[3,4-c]cinnoline-1,5-dioxides

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• 作者：V. P. Zelenov (1)
  A. A. Voronin (1)
  A. M. Churakov (1) churakov@ioc.ac.ru
  M. S. Klenov (1)
  Yu. A. Strelenko (1)
  V. A. Tartakovsky (1)
• 关键词：Key words N ; nitramines – ; furoxanes – ; cinnolines – ; oxodiazonium ion – ; nitration – ; 1H – ; 13C – ; 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：2046-2050
• 全文大小：235.8 KB
• 参考文献：1. M. S. Klenov, V. P. Zelenov, A. M. Churakov, Yu. A. Strelenko, V. A. Tartakovsky, Izv. Akad. Nauk, Ser. Khim., 2011, 2003 [Russ. Chem. Bull., Int. Ed., 2011, 60, 2040].
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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 reaction of 4-(N-nitramino)-3-phenylfuroxane with the Ac₂O/H₂SO₄ system leads to the formation of [1,2,5]oxadiazolo[3,4-c]cinnoline-1,5-dioxide, the first representative of furoxanocinnolines. The reaction presumably proceeds through the transformation of the nitramine fragment NHNO₂ to the oxodiazonium ion [N=N=O]+ with subsequent intramolecular attack by this cation on the phenyl ring. Furoxanocinnoline is also formed in the reaction of the 4-(N-nitramino)-3-phenylfuroxane O-methyl derivative with H₂SO₄. It is assumed that this reaction also proceeds with involvement of the intermediate cation [N=N=O]+ formed by the protonation of the N=N(O)OMe group and subsequent elimination of MeOH. 7-Nitro derivative is formed when furoxanocinnoline is nitrated with the concentrated HNO₃/H₂SO₄ mixture. The compounds obtained were characterized by 1H, 13C, and 14N NMR spectroscopy.