Download PDF
Synthesis 2009(7): 1131-1136  
DOI: 10.1055/s-0028-1088004
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Three-Component Coupling of Isoquinoline, Activated Alkyne and Nitromethane: A Facile Synthesis of Nitromethyl Derivatives of 1,2-Dihydroisoquinolines

Jhillu S. Yadav*, Basi V. Subba Reddy, Nagendra Nath Yadav, Manoj K. Gupta
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: yadav@iict.res.in;
Further Information

Publication History

Received 10 November 2008
Publication Date:
06 March 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

A three-component coupling (3CC) of isoquinoline, activated alkynes and nitromethane has been achieved for the first time to produce nitromethyl derivatives of dihydroisoquinoline in excellent yields with high selectivity. The reaction proceeds smoothly at 25 ˚C without catalyst.

Key words

aza-Henry reaction - isoquinoline/quinoline - activated alkynes - nitromethane

    References

  • 1a Ramon DJ. Yus M. Angew. Chem. Int. Ed.  2005,  44:  1602 
    Google Scholar
  • 1b Nair V. Rajesh C. Vinod AU. Bindu S. Sreekenth AR. Balagopal L. Acc. Chem. Res.  2003,  36:  899 
    Google Scholar
  • 1c Orru RVA. de Greef M. Synthesis  2003,  1471 
    Google Scholar
  • 1d Balme G. Bossharth E. Monteiro N. Eur. J. Org. Chem.  2003,  4101 
    Google Scholar
  • 1e Domling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
    Google Scholar
  • 1f Bienayme H. Hulme C. Oddon G. Schmitt P. Chem. Eur. J.  2000,  3321 
    Google Scholar
  • 1g Weber L. Illgen K. Almstetter M. Synlett  1999,  366 
    Google Scholar
  • 2a Scott JD. Williams RM. Chem. Rev.  2002,  102:  1669 
    Google Scholar
  • 2b Chan C. Heid R. Zheng S. Guo J. Zhou B. Furuuchi T. Danishefsky SJ. J. Am. Chem. Soc.  2005,  127:  4596 
    Google Scholar
  • 2c Vincent G. Williams RM. Gan EF. Williams RM. Angew. Chem. Int. Ed.  2007,  46:  1517 
    Google Scholar
  • 3a Gensler WJ. Lawless SF. Bluhm AL. Dertouzos H. J. Org. Chem.  1975,  40:  733 
    Google Scholar
  • 3b Beugelmans R. Chastanet J. Roussi G. Tetrahedron  1984,  40:  311 
    Google Scholar
  • 3c Magnus P. Matthew KS. Lynch V. Org. Lett.  2003,  5:  2181 
    Google Scholar
  • 3d Kadzimirsz D. Hildebrandt D. Merz K. Dyker G. Chem. Commun.  2006,  661 
    Google Scholar
  • 4a Miller RB. Tetrahedron Lett.  1998,  39:  1721 
    Google Scholar
  • 4b Lorsbach BA. Bagdanoff JT. Miller RB. Kurth MJ. J. Org. Chem.  1998,  63:  2244 
    Google Scholar
  • 4c Lee SH. Park YS. Nam MH. Yoon CM. Org. Biomol. Chem.  2004,  2:  2170 
    Google Scholar
  • 4d Taylor SJ. Taylor AM. Schreiber SL. Angew. Chem. Int. Ed.  2004,  43:  1681 
    Google Scholar
  • 4e Diaz JL. Miguel M. Lavilla R. J. Org. Chem.  2004,  69:  3550 
    Google Scholar
  • 4f Ullah E. Rotzoll S. Schmidt A. Michalik D. Langer P. Tetrahedron Lett.  2005,  46:  8997 
    Google Scholar
  • 4g Hewavitharanage P. Danilov EO. Neckers DC. J. Org. Chem.  2005,  70:  10653 
    Google Scholar
  • 5a Takamura M. Funbashi K. Kanai M. Shibasaki M. J. Am. Chem. Soc.  2000,  122:  6327 
    Google Scholar
  • 5b Funabashi K. Ratni H. Kanai M. Shibasaki M. J. Am. Chem. Soc.  2001,  123:  10784 
    Google Scholar
  • 5c Alexakis A. Amiot F. Tetrahedron: Asymmetry  2002,  13:  2117 
    Google Scholar
  • 5d Taylor MS. Tokunaga N. Jacobsen EN. Angew. Chem. Int. Ed.  2005,  44:  6700 
    Google Scholar
  • 5e Taylor AM. Schreiber SL. Org. Lett.  2006,  8:  143 
    Google Scholar
  • 5f Lu S. Wang Y. Han X. Zhau Y. Angew. Chem. Int. Ed.  2006,  45:  2260 
    Google Scholar
  • 6a Yadav JS. Reddy BVS. Gupta MK. Prabhakar A. Jagadeesh B. Chem. Commun.  2004,  2124 
    Google Scholar
  • 6b Yadav JS. Reddy BVS. Srinivas M. Sathaiah K. Tetrahedron Lett.  2005,  46:  3489 
    Google Scholar
  • 6c Yadav JS. Reddy BVS. Srinivas M. Sathaiah K. Tetrahedron Lett.  2005,  46:  8905 
    Google Scholar
  • 6d Yadav JS. Reddy BVS. Gupta MK. Prahap I. Dash U. Synthesis  2007,  1077 
    Google Scholar
  • 6e Yadav JS. Reddy BVS. Gupta MK. Dash U. Bhunia DC. Hossain SS. Synlett  2007,  2801 
    Google Scholar
  • 7a Yadav JS. Reddy BVS. Yadav NN. Gupta MK. Sridhar B. J. Org. Chem.  2008,  73:  6857 
    Google Scholar
  • 7b Yadav JS. Reddy BVS. Yadav NN. Gupta MK. Tetrahedron Lett.  2008,  49:  2815 
    Google Scholar
  • 8a Winterfeldt E. Angew. Chem. Int. Ed. Engl.  1967,  6:  424 
    Google Scholar
  • 8b Johnson AW. Tebby JC. J. Chem. Soc.  1961,  2126 
    Google Scholar
  • 8c Tebby JC. Wilson IF. Griffiths DV. J. Chem. Soc., Perkin Trans. 1  1979,  2133 
    Google Scholar
  • 8d Butterfield PJ. Tebby JC. Griffiths DV. J. Chem. Soc., Perkin Trans. 1  1979,  1189 
    Google Scholar