Synthesis of pyrazole- and thiazole-annulated 3-R-1,5-dinitro-3-azabicyclo[3.3.1]nonanes

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• 作者：A. V. Puchnin (1)
  M. A. Bastrakov (2)
  A. M. Starosotnikov (2)
  S. V. Popkov (1)
  S. A. Shevelev (2)
  
• 关键词：azabicyclo[3.3.1]nonanes ; reduction ; Mannich reaction ; nitro group ; azoles
• 刊名：Russian Chemical Bulletin
• 出版年：2012
• 出版时间：March 2012
• 年：2012
• 卷：61
• 期：3
• 页码：596-599
• 全文大小：230KB
• 参考文献：1. M. A. Bastrakov, A. M. Starosotnikov, A. Kh. Shakhnes, S. A. Shevelev, / Izv. Akad. Nauk, Ser. Khim., 2008, 1508 [ / Russ. Chem. Bull., Int. Ed., 2008, 57, 1539]; M. A. Bastrakov, A. M. Starosotnikov, V. V. Kachala, I. V. Glukhov, S. A. Shevelev, / Izv. Akad. Nauk, Ser. Khim., 2009, 407 [ / Russ. Chem. Bull., Int. Ed., 2009, 58, 414].
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  9. E. M. Asadulina, M. A. Bastrakov, V. V. Kachala, A. M. Starosotnikov, S. A. Shevelev, / Mendeleev Commun., 2008, 213; E. M. Asadulina, M. A. Bastrakov, A. M. Starosotnikov, V. V. Kachala, S. A. Shevelev, / Izv. Akad. Nauk, Ser. Khim., 2009, 413 [ / Russ. Chem. Bull., Int. Ed., 2009, 58, 421].
  10. A. M. Starosotnikov, A. V. Lobach, V. V. Kachala, S. A. Shevelev, / Izv. Akad. Nauk, Ser. Khim., 2004, 557 [ / Russ. Chem. Bull., Int. Ed., 2004, 53, 584].
  11. A. M. Kuvshinov, V. I. Gulevskaya, V. V. Rozhkov, S. A. Shevelev, Synthesis, 2000, 1474; D. A. Brovko, V. N. Marshalkin, V. V. Semenov, / Khim. Geterotsikl. Soedin., 2001, 552 [ / Chem. Heterocycl. Compd. ( / Engl. Transl.), 2001, 37, 504].
  12. E. Buncel, M. R. Crampton, M. J. Strauss, F. Terrier, / Electron Deficient Aromatic- and Heteroaromatic-base Interactions, Elsevier, Amsterdam, 1984, p. 422.
  13. J. W. Dehn, R. Eltonhead, R. A. Pizzarello, US Pat. 3057848; m/publicationDetails/biblio?CC=US&NR=3057848A&KC=A&FT=D&ND=6&-date=19621009&DB=worldwide.espacenet.com&locale=en_EP">http://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=3057848A&KC=A&FT=D&ND=6&-date=19621009&DB=worldwide.espacenet.com&locale=en_EP.
  
• 作者单位：A. V. Puchnin (1)
  M. A. Bastrakov (2)
  A. M. Starosotnikov (2)
  S. V. Popkov (1)
  S. A. Shevelev (2)
  
  1. D. I. Mendeleev University of Chemical Technology of Russia, 9 pl. Miusskaya, 125047, Moscow, Russian Federation
  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
  
• ISSN：1573-9171

文摘

The previously unknown 3-R-1,5-dinitro-3-azabicyclo[3.3.1]nonanes fused to the pyrazole or thiazole rings were synthesized by the reductive cyclization of m-dinitroindazoles and benzothiazoles. The method is based on the reduction of carbon-carbon bonds in the benzene ring, which are activated by the meta-nitro groups, with NaBH4 followed by the Mannich reaction with formaldehyde and primary amines.