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Synthesis 2010(19): 3268-3270  
DOI: 10.1055/s-0030-1258219
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Synthesis of 1,1′-Dialkylisoindigos through Deoxygenation Reaction of Isatins and Tris(diethylamino)phosphine

Andrei V. Bogdanov*, Vladimir F. Mironov, Lenar I. Musin, Rashid Z. Musin
A.E. Arbuzov Institute of Organic and Physical Chemistry, KSC RAS, str. acad. Arbuzova 8, Kazan 420088, Russian Federation
Fax: +7(843)2732253; e-Mail: bogdanov@iopc.knc.ru;
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Publikationsverlauf

Received 19 March 2010
Publikationsdatum:
17. August 2010 (online)

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Abstract

A convenient one-step synthesis of symmetrical 1,1′-dialkyl derivatives of isoindigo is described.

Key words

carbenes - deoxygenation - heterocycles - regioselectivity - phosphorus

    References

  • 1 Lee J. Bansal T. Jayaraman A. Bentley WE. Wood TK. Appl. Environ. Microbiol.  2007,  73:  4100 
    CrossrefGoogle Scholar
  • 2 Sassatelli M. Bouchikhi F. Aboab B. Anizon F. Fabbro D. Prudhomme M. Moreau P. Anti-Cancer Drugs  2007,  18:  1069 
    CrossrefGoogle Scholar
  • 3 Rui L. Reardon KF. Wood TK. Appl. Microbiol. Biotechnol.  2000,  66:  422 
    CrossrefGoogle Scholar
  • 4 Sassatelli M. Saab E. Anizon F. Prudhomme M. Moreau P. Tetrahedron Lett.  2004,  45:  4827 
    CrossrefGoogle Scholar
  • 5 Lathourakis GE. Litinas KE. J. Chem. Soc., Perkin Trans. 1  1996,  491 
    CrossrefGoogle Scholar
  • 6 Islam MR. Khayer Kh. Akhter A. Duddeck H. J. Bangladesh Chem. Soc.  2005,  18:  1 
    Google Scholar
  • 7 Osman FH. El-Samahy FA. Chem. Rev.  2002,  102:  629 
    CrossrefPubMedGoogle Scholar
  • 8 Hahn FE. Jahnke MC. Angew. Chem. Int. Ed.  2008,  47:  3122 
    Google Scholar
  • 9 Bogdanov AV. Mironov VF. Buzykin BI. Konovalov AI. Russ. J. Gen. Chem. (Engl. Transl.)  2005,  75:  825 
    CrossrefGoogle Scholar
  • 10 Bogdanov AV. Mironov VF. Buzykin BI. Konovalov AI. Russ. J. Gen. Chem. (Engl. Transl.)  2008,  78:  1977 
    CrossrefGoogle Scholar
  • 11 Romanova IP. Bogdanov AV. Mironov VF. Larionova OA. Latypov ShK. Balandina AA. Yakhvarov DG. Sinyashin OG. Mendeleev Commun.  2009,  19:  306 
    CrossrefGoogle Scholar
  • 12 Tacconi G. Righetti PP. Desimoni G. J. Prakt. Chem.  1973,  315:  339 
    CrossrefGoogle Scholar
  • 13a Kormachev VV. Fedoseyev NS. Preparative Phosphorus Chemistry   UrO RAN; Perm: 1992. 
    Google Scholar
  • 13b Stuebe C. Lankelma HP. J. Am. Chem. Soc.  1956,  78:  976 
    Google Scholar
  • 14 Stolle R. J. Prakt. Chem.  1930,  128:  1 
    CrossrefGoogle Scholar
  • 15 Harley-Mason J. Ingleby RT. J. Chem. Soc.  1958,  4782 
    Google Scholar
  • 16 Banerji A. Maiti S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1994,  33:  532 
    Google Scholar