Synthesis 2008(20): 3326-3330  
DOI: 10.1055/s-0028-1083143
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A General Procedure to Access Methylene Ether Isonitrile Derivatives

Rebecca L. Grangea, Craig M. Williams*a, Lin Donga, Victoria A. Gordonb
a School of Molecular and Microbial Sciences, University of Queensland, Brisbane 4072, Australia
Fax: +61(7)33654299; e-Mail: c.williams3@uq.edu.au;
b EcoBiotics Limited, PO Box 1, Yungaburra 4884, Australia
Further Information

Publication History

Received 29 April 2008
Publication Date:
25 September 2008 (online)

Abstract

Isonitriles are essential building blocks for multicomponent reactions. A convenient and simple two-step synthesis of the little known methylene ether isonitrile derivatives is presented.

    References

  • See, for example:
  • 1a Zhu J. Eur. J. Org. Chem.  2003,  1133 
  • 1b Dömling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
  • 1c Hulme C. Nixey T. Curr. Opin. Drug Discovery Dev.  2003,  6:  921 
  • 1d Tempest PA. Curr. Opin. Drug Discovery Dev.  2005,  8:  776 
  • See, for example:
  • 2a Ranganathan S. Singh WP. Tetrahedron Lett.  1988,  29:  1435 
  • 2b van Leusen AM. Wildeman J. Moskal J. van Hemert AW. Recl. Trav. Chim. Pays-Bas  1985,  104:  177 
  • 2c Saikachi H. Sasaki H. Kitagawa T. Chem. Pharm. Bull.  1983,  31:  723 
  • 2d van Leusen AM. Schut J. Tetrahedron Lett.  1976,  285 
  • 2e Schöllkopf U. Gerhart F. Hoppe I. Harms R. Hantke K. Scheunemann KD. Eilers E. Blume E. Liebigs Ann. Chem.  1976,  183 
  • 2f van Leusen AM. van Gennep HE. Tetrahedron Lett.  1973,  14:  627 
  • 2g Schöllkopf U. Blume E. Tetrahedron Lett.  1973,  14:  629 
  • 2h Mąkosza M. Kinowski A. Ostrowski S. Synthesis  1993,  1215 
  • See, for example:
  • 3a Hao G. Zang J. Liu B. J. Labelled Compd. Radiopharm.  2007,  50:  13 
  • 3b Bergstein PL, and Subramanyam V. inventors; European Patent EP  0233368.  ; Chem. Abstr. 1988, 108, 164179
  • 3c Nishiyama T. Isobe M. Ichikawa Y. Angew. Chem. Int. Ed.  2005,  44:  4372 
  • 3d Boullanger P. Marmet D. Descotes G. Tetrahedron  1979,  35:  163 
  • 3e Prosperi D. Ronchi S. Lay L. Rencurosi A. Russo G. Eur. J. Org. Chem.  2004,  395 
  • 4 Yoshida J. Itoh M. Morita Y. Isoe S. J. Chem. Soc., Chem. Commun.  1994,  549 
  • 5 Sasaki H. Chem. Pharm. Bull.  1997,  45:  1369 
  • 6 Gate NE. Threadgill MD. Stevens MFG. Chubb D. Vickers LM. Langdon SP. Hickman JA. Gescher A. J. Med. Chem.  1986,  29:  1046 
  • 7 Suginome M. Ito Y. In Science of Synthesis   Vol. 19:  Murahashi S.-I. Thieme; Stuttgart: 2004.  p.445 
  • See, for example:
  • 8a Morishima I. Mizuno A. Yonezawa T. J. Chem. Soc., Chem. Commun.  1970,  1321 
  • 8b Stephany RW. de Bie MJA. Drenth W. Org. Magn. Reson.  1974,  6:  45 
  • 8c Pretsch E. Tables of Spectral Data for Structure Determination of Organic Compounds   Springer-Verlag; Berlin: 1983.