Download PDF
Synthesis 2012(3): 417-422  
DOI: 10.1055/s-0031-1289666
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile Multicomponent Reaction Involving Isoquinoline, Dimethyl Allenedicarboxylate, and 2-Oxo-1H-indol-3-ylidenes

Rejithamol Rajana, Beneesh Pattoorpadi Babua, Amit Kumara, Rony Rajan Paula, C. R. Sinua, Eringathodi Sureshb, Vijay Nair*a
a Organic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695 019, India
Fax: +91(471)2491712; e-Mail: vijaynair_2001@yahoo.com;
b Analytical Science Division, Central Salt and Marine Research Institute, Bhavanagar 364 002, India
Further Information

Publication History

Received 11 October 2011
Publication Date:
04 January 2012 (online)

    Permissions and Reprints All articles of this category

Abstract

Transient zwitterions generated from dimethyl allenedicarboxylate and isoquinoline were successfully intercepted with 2-oxo-1H-indol-3-ylidenes to result in a facile multicomponent reaction under mild conditions.

Key words

zwitterions - allenes - multicomponent reactions - indoles - isoquinoline

    References

  • 1 Diels O. Alder K. Liebigs Ann. Chem.  1932,  498:  16 
    Google Scholar
  • 2a Acheson RM. Gagan JMF. Taylor GA. J. Chem. Soc.  1963,  1903 
    Google Scholar
  • 2b Acheson RM. Woollard J. J. Chem. Soc., Perkin Trans. 1  1975,  438 
    Google Scholar
  • 3a Huisgen R. Morikawa M. Herbig K. Brunn E. Chem. Ber.  1967,  100:  1094 
    Google Scholar
  • 3b Huisgen R. Z. Chem.  1968,  8:  290 
    Google Scholar
  • 4 Crabtree A. Johnson AW. Tebby JC. J. Chem. Soc.  1961,  3497 
    Google Scholar
  • 5a Nair V. Rajesh C. Vinod AU. Bindu S. Sreekanth AR. Mathen JS. Balagopal L. Acc. Chem. Res.  2003,  36:  899 
    Google Scholar
  • 5b Nair V. Remadevi B. Varma L. Tetrahedron Lett.  2005,  46:  5333 
    Google Scholar
  • 6 Butler MS. J. Nat. Prod.  2004,  67:  2141 
    Google Scholar
  • 7 Padwa A. Prog. Heterocycl. Chem.  1994,  6:  36 
    Google Scholar
  • For a review, see:
  • 8a Nair V. Menon RS. Sreekanth AR. Abhilash N. Biju AT. Acc. Chem. Res.  2006,  39:  520 
    Google Scholar
  • 8b Nair V. Sreekanth AR. Abhilash N. Bhadbhade M. Gonnade RC. Org. Lett.  2002,  4:  3575 
    Google Scholar
  • 8c Nair V. Devi RB. Pillai AN. Paul RR. Heterocycles  2007,  73:  249 
    Google Scholar
  • 8d Nair V. Devipriya S. Suresh E. Synthesis  2008,  1065 
    Google Scholar
  • 8e Alizadeh A. Rostmania S. Synthesis  2010,  1543 
    Google Scholar
  • 8f Reddy BVS. Somasekhar D. Yadav JS. Sridhar B. Synthesis  2010,  2069 
    Google Scholar
  • 8g Dömling A. Huang Y. Synthesis  2010,  2859 
    Google Scholar
  • 9 Krause N. Hashmi ASK. In Modern Allene Chemistry   Vols. 1-2:  Wiley-VCH; Weinheim: 2004. 
    Google Scholar
  • 10a Ma S. Chem. Rev.  2005,  105:  2829 
    Google Scholar
  • 10b Lu X. Zhang C. Xu Z. Acc. Chem. Res.  2001,  34:  535 
    Google Scholar
  • 11 Nair V. Babu BP. Varghese V. Sinu CR. Paul RR. Anabha ER. Tetrahedron Lett.  2009,  50:  3716 
    Google Scholar