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Synthesis 2010(10): 1719-1723  
DOI: 10.1055/s-0029-1218721
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Three-Component Reaction of a δ-Hydroxy-α,β-Unsaturated Aldehyde with Arylamines and 1,3-Diketones: A Novel Synthesis of Oxa-Aza Bicycles

Basi V. Subba Reddy*a, Ch. Divyavania,b, Zubeda Beguma, Jhillu S. Yadava
a Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: basireddy@iict.res.in;
b IICT - An Associate Institution of the University of Hyderabad, Hyderabad 500007, India
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Publikationsverlauf

Received 8 February 2010
Publikationsdatum:
06. April 2010 (online)

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Abstract

δ-Hydroxy-α,β-unsaturated sugar aldehydes (Perlin aldehydes) undergo smooth coupling with β-enamino ketones and β-enamino esters generated in situ from arylamines and 1,3-dicarbonyl compounds in the presence of 10 mol% InCl3 in acetonitrile at 80 ˚C, to produce oxa-aza-bicycles in good yields with high selectivity.

Key words

Perlin aldehyde - 1,3-dicarbonyl compounds - indium salts - oxa-aza-bicycles

    References

  • 1 Zhu J. Bienayme H. Multi-Component Reactions   Wiley-VCH; Weinheim: 2005. 
  • 2a Gonzalez F. Leasage S. Perlin AS. Carbohydr. Res.  1975,  42:  267 
    Suche in Google Scholar
  • 2b Mukhopadhyay A. Suryawanshi SN. Bhakuni DS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1988,  27:  1009 
    Suche in Google Scholar
  • 2c Sagar R. Pathak R. Shaw AK. Carbohydr. Res.  2004,  339:  2031 ; and references cited therein
    Suche in Google Scholar
  • 3a Tulshian DB. Fraser-Reid B. J. Am. Chem. Soc.  1981,  103:  474 
    Suche in Google Scholar
  • 3b Tolstikov AG. Khakhalina NV. Spirikhin LV. Synthesis  1988,  221 
  • 3c Pathak R. Shaw AK. Bhaduri AP. Chandrasekhar KVG. Srivastava A. Srivastava KK. Chaturvedi V. Srivastava R. Srivastava BS. Arora S. Sinha S. Bioorg. Med. Chem.  2002,  10:  1695 
    Suche in Google Scholar
  • 3d Pathak R. Shaw AK. Bhaduri AP. Tetrahedron  2002,  58:  3535 
    Suche in Google Scholar
  • 3e Sagar R. Singh P. Kumar R. Maulik PR. Shaw AK. Carbohydr. Res.  2005,  340:  1287 
    Suche in Google Scholar
  • 4a Kaluza Z. Chmielewski M. Pedersen EB. Heterocycles  1988,  27:  1313 
    Suche in Google Scholar
  • 4b Wengel J. Lau J. Pedersen EB. Synthesis  1989,  829 
  • 4c Lau J. Wengel J. Pedersen EB. Vestergaard BF. Synthesis  1991,  1183 
  • 4d Wengel J. Pedersen EB. Vestergaard BF. Synthesis  1992,  319 
  • 4e Singh SK. Parmar VS. Wengel J. Tetrahedron Lett.  1996,  37:  7619 
    Suche in Google Scholar
  • 5 Turner CI. Williamson RM. Turner P. Sherburn MS. Chem. Commun.  2003,  1610 ; and references cited therein
    Crossref
  • 6a Yadav JS. Reddy BVS. Parimala G. Raju AK. Tetrahedron Lett.  2004,  45:  1543 
    Suche in Google Scholar
  • 6b Yadav JS. Reddy BVS. Padmavani B. Synthesis  2004,  405 
  • 6c Yadav JS. Sunitha V. Reddy BVS. Das PP. Gyanchander E. Tetrahedron Lett.  2008,  49:  855 
    Suche in Google Scholar
  • 7a Yadav JS. Reddy BVS. Satheesh G. Srinivasulu G. Kunwar AC. ARKIVOC  2005,  (iii):  221 
    Suche in Google Scholar
  • 7b Yadav JS. Raju AK. Sunitha V. Tetrahedron Lett.  2006,  47:  5269 
    Suche in Google Scholar
  • 8a Yadav JS. Reddy BVS. Satheesh G. Narasimhulu G. Portier Y. Madavi Ch. Kunwar AC. Tetrahedron Lett.  2008,  49:  3341 
    Suche in Google Scholar
  • 8b Yadav JS. Reddy BVS. Srinivas M. Prabhakar A. Jagadeesh B. Tetrahedron Lett.  2004,  45:  6033 
    Suche in Google Scholar
  • 8c Yadav JS. Reddy BVS. Srinivas M. Divyavani Ch. Kunwar AC. Madavi Ch. Tetrahedron Lett.  2007,  48:  8301 
    Suche in Google Scholar
  • 9a Yadav JS. Reddy BVS. Satheesh G. Lakshmi PN. Kumar SK. Kunwar AC. Tetrahedron Lett.  2004,  43:  8587 
    Suche in Google Scholar
  • 9b Yadav JS. Reddy BVS. Srinivas M. Divyavani Ch. Basha J. Sarma AVS. J. Org. Chem.  2008,  73:  3252 
    Suche in Google Scholar
  • 9c Yadav JS. Reddy BVS. Swamy DN. Lakshmi PN. Narsimhulu K. Srinivasulu G. Kunwar AC. Tetrahedron Lett.  2004,  45:  493 
    Suche in Google Scholar