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Synthesis 2011(24): 3997-4002  
DOI: 10.1055/s-0031-1289592
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of Isocyanides from Alcohols

Iku Okada, Yoshikazu Kitano*
Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu-shi, Tokyo 183-8509, Japan
Fax: +81(42)3675700; e-Mail: kitayo@cc.tuat.ac.jp;
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Publikationsverlauf

Received 30 August 2011
Publikationsdatum:
04. November 2011 (online)

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Abstract

A one-pot reaction of alcohols with trimethylsilyl cyanide and methanesulfonic acid with subsequent neutralization by triethylamine and dehydration by tosyl chloride and pyridine gave the corresponding isocyanides in moderate-to-high yields. This method was used to synthesize tertiary and benzylic isocyanides from the corresponding alcohols.

Key words

isocyanides - alcohols - Ritter reactions

    References

  • 1a Passerini M. Gazz. Chim. Ital.  1921,  51:  126 
    Suche in Google Scholar
  • 1b Ugi I. Betz W. Fetzer U. Offerman K. Chem. Ber.  1961,  94:  2814 
    Suche in Google Scholar
  • 1c Isonitrile Chemistry   Ugi I. Academic Press; New York: 1971. 
  • 1d Dömling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
    Suche in Google Scholar
  • 1e Ugi I. Dömling A. In Combinatorial Chemistry: A Practical Approach   Fenniri H. Oxford University Press; Oxford: 2000.  p.287 
  • 1f Dömling A. Curr. Opin. Chem. Biol.  2000,  4:  318 
    Suche in Google Scholar
  • 1g Ugi I. Werner B. Dömling A. In Targets in Heterocyclic Systems: Chemistry and Properties   Attanasi OA. Filippone P. Società Chimica Italiana; Rome: 2000. 
  • 2a Li X. Danishefsky SJ. J. Am. Chem. Soc.  2008,  130:  5446 
    Suche in Google Scholar
  • 2b Li X. Danishefsky SJ. Nat. Protoc.  2008,  3:  1666 
    Suche in Google Scholar
  • 2c Li X. Yuan Y. Berkowitz WF. Todaro LJ. Danishefsky SJ. J. Am. Chem. Soc.  2008,  130:  13222 
    Suche in Google Scholar
  • 2d Li X. Yuan Y. Kan C. Danishefsky SJ. J. Am. Chem. Soc.  2008,  130:  13225 
    Suche in Google Scholar
  • 2e Wu X. Li X. Danishefsky SJ. Tetrahedron Lett.  2009,  50:  1523 
    Suche in Google Scholar
  • 2f Yuan Y. Zhu J. Li X. Wu X. Danishefsky SJ. Tetrahedron Lett.  2009,  50:  2329 
    Suche in Google Scholar
  • 2g Rao Y. Li X. Danishefsky SJ. J. Am. Chem. Soc.  2009,  131:  12924 
    Suche in Google Scholar
  • 2h Wu X. Stocdill JL. Wang P. Danishefsky SJ.
    J. Am. Chem. Soc.  2010,  132:  4098 
    Suche in Google Scholar
  • 2i Wu X. Park PK. Danishefsky SJ. J. Am. Chem. Soc.  2011,  133:  7700 
    Suche in Google Scholar
  • 3a Fusetani N. Nat. Prod. Rep.  2004,  21:  94 
    Suche in Google Scholar
  • 3b Garson MJ. Simpson JS. Nat. Prod. Rep.  2004,  21:  164 
    Suche in Google Scholar
  • 4a Kitano Y. Ito T. Suzuki T. Nogata Y. Shinshima K. Yoshimura E. Chiba K. Tada M. Sakaguchi I. J. Chem. Soc., Perkin Trans. 1  2002,  2251 
  • 4b Kitano Y. Yokoyama A. Nogata Y. Shinshima K. Yoshimura E. Chiba K. Tada M. Sakaguchi I. Biofouling  2003,  19 (Suppl. 1):  187 
    Suche in Google Scholar
  • 4c Nogata Y. Kitano Y. Yoshimura E. Shinshima K. Sakaguchi I. Biofouling  2004,  20:  87 
    Suche in Google Scholar
  • 4d Kitano Y. Nogata Y. Shinshima K. Yoshimura E. Chiba K. Tada M. Sakaguchi I. Biofouling  2004,  20:  93 
    Suche in Google Scholar
  • 4e Kitano Y. Akima C. Yoshimura E. Nogata Y. Biofouling  2011,  27:  201 
    Suche in Google Scholar
  • 5a Baldwin JE. O’Neil IA. Synlett  1990,  603 
  • 5b Launay D. Booth S. Clemens I. Merritt A. Bradley M. Tetrahedron Lett.  2002,  43:  7201 
    Suche in Google Scholar
  • 5c Porcheddu A. Giacomelli G. Salaris M. J. Org. Chem.  2005,  70:  2361 
    Suche in Google Scholar
  • 5d Kim S. Yi KY. Tetrahedron Lett.  1986,  27:  1925 
    Suche in Google Scholar
  • 5e Creedon SM. Crowley HK. McCarthy DG. J. Chem. Soc., Perkin Trans. 1  1998,  1015 
  • 5f Bose DS. Goud PR. Tetrahedron Lett.  1999,  40:  747 
    Suche in Google Scholar
  • 6a Kitano Y. Chiba K. Tada M. Tetrahedron Lett.  1998,  39:  1911 
    Suche in Google Scholar
  • 6b Kitano Y. Chiba K. Tada M. Synthesis  2001,  437 
  • 7 Chen HG. Goel OP. Kesten S. Knobelsdolf J. Tetrahedron Lett.  1996,  37:  8129 
    Suche in Google Scholar
  • 8a Booth MR. Frankiss SG. J. Chem. Soc., Chem. Commun.  1968,  1347 
  • 8b Reetz MT. Chatziiosifidis I. Künzer H. Müller-Starke H. Tetrahedron  1983,  39:  961 
    Suche in Google Scholar
  • 8c Zieger HE. Wo S. J. Org. Chem.  1994,  59:  3838 
    Suche in Google Scholar
  • 9 Sasaki T. Eguchi S. Katada T. J. Org. Chem.  1974,  39:  1239 
    Suche in Google Scholar
  • 10 Kobayashi G. Saito T. Kitano Y. Synthesis  2011,  3225 
  • 11 Kitano Y. Manoda T. Miura T. Chiba K. Tada M. Synthesis  2006,  405 
  • 12 Kitano Y. Nogata Y. Matsumura K. Yoshimura E. Chiba K. Tada M. Sakaguchi I. Tetrahedron  2005,  61:  9969 
    Suche in Google Scholar