Synthesis, structure, and antibacterial activity of aminobenzofuroxan and aminobenzofurazan

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• 作者：I. V. Galkina (1298)
  G. L. Takhautdinova (1298)
  E. V. Tudrii (1298)
  L. M. Yusupova (2298)
  I. F. Falyakhov (2298)
  O. K. Pozdeev (3298)
  M. P. Shulaeva (3298)
  L. V. Kipenskaya (3298)
  V. G. Sakhibullina (1298)
  D. B. Krivolapov (4298)
  I. A. Litvinov (4298)
  V. I. Galkin (1298)
  R. A. Cherkasov (1298)
  
• 刊名：Russian Journal of Organic Chemistry
• 出版年：2013
• 出版时间：April 2013
• 年：2013
• 卷：49
• 期：4
• 页码：591-597
• 全文大小：417KB
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• 作者单位：I. V. Galkina (1298)
  G. L. Takhautdinova (1298)
  E. V. Tudrii (1298)
  L. M. Yusupova (2298)
  I. F. Falyakhov (2298)
  O. K. Pozdeev (3298)
  M. P. Shulaeva (3298)
  L. V. Kipenskaya (3298)
  V. G. Sakhibullina (1298)
  D. B. Krivolapov (4298)
  I. A. Litvinov (4298)
  V. I. Galkin (1298)
  R. A. Cherkasov (1298)
  
  1298. Kazan (Volga Region) Federal University, ul. Kremlevskaya 18, Kazan, 420008, Tatarstan, Russia
  2298. Kazan National Research Technological University, ul. K. Marksa 68, Kazan, 420015, Tatarstan, Russia
  3298. Kazan State Medical Academy, ul. Mushtari 11, Kazan, 420012, Tatarstan, Russia
  4298. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia
  
• ISSN：1608-3393

文摘

The amination of 4,6-dichloro-5,7-dinitrobenzofuroxan and 4,6-dichloro-5,7-dinitrobenzofurazan with dibenzylamine followed the aromatic nucleophilic substitution pattern (SNAr) and gave products of replacement of both chlorine atoms in the six-membered ring with elimination of hydrogen chloride. Regardless of the reactant ratio, 4,6-dichloro-5,7-dinitrobenzofuroxan was converted into 4,6-bis(dibenzylamino)-5,7-dinitrobenzofuroxan, whereas 4,6-dichloro-5,7-dinitrobenzofurazan under analogous conditions gave rise to unusual bisammonium derivative which lost proton from the amino group on C4 and benzyl group from the amino group on C6; as a result, the corresponding diamine with secondary and tertiary nitrogen atoms was obtained. The structure of the isolated compounds was determined by IR and NMR spectroscopy, elemental analysis, and X-ray analysis; their thermal stability was studied by simultaneous thermogravimetry and differential scanning calorimetry.