Download PDF
Synlett 2009(9): 1401-1404  
DOI: 10.1055/s-0029-1217184
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Isocyanide-Based Multicomponent Reaction ‘without’ Isocyanides

Laurent El Kaim, Laurence Grimaud*, Aurélie Schiltz
Laboratoire Chimie et Procédés, Ecole Nationale Supérieure de Techniques Avancées, 32 Boulevard Victor, 75739 Paris Cedex 15, France
Fax: +33(1)45528322; e-Mail: laurent.elkaim@ensta.fr; e-Mail: laurence.grimaud@ensta.fr;
Further Information

Publication History

Received 17 February 2009
Publication Date:
18 May 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

We present here a one-pot, four-component sequence that affords Ugi-type adducts starting from simple benzyl or allyl bromides. The isocyanides are prepared in situ under alkylation of silver cyanide salts and the resulting mixture is directly used in a Ugi-Smiles coupling.

Key words

isocyanides - synthesis - alkylation - silver cyanide - Ugi-Smiles - multicomponent reaction

    References and Notes

  • 1 Lieke W. Justus Liebigs Ann. Chem.  1859,  112:  316 
    Google Scholar
  • 2a Passerini M. Gazz. Chim. Ital.  1921,  51:  126 
    Google Scholar
  • 2b Passerini M. Gazz. Chim. Ital.  1921,  51:  180 
    Google Scholar
  • 2c For a recent review on Passerini reaction, see: Banfi L. Riva R. Org. React.  2005,  65:  1 
    Google Scholar
  • 3a Ugi I. Meyr R. Fetzer U. Steinbrückner C. Angew. Chem.  1959,  71:  386 
    Google Scholar
  • 3b Ugi I. Steinbrückner C. Angew. Chem.  1960,  72:  267 
    Google Scholar
  • For recent reviews, see:
  • 3c Dömling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
    Google Scholar
  • 3d Bienaymé H. Hulme C. Oddon G. Schmitt P. Chem. Eur. J.  2000,  6:  3321 
    Google Scholar
  • 3e Ugi I. Werner B. Dömling A. Molecules  2003,  8:  53 
    Google Scholar
  • 3f Dömling A. Curr. Opin. Chem. Biol.  2002,  6:  306 
    Google Scholar
  • 3g Multicomponent reactions   Zhu J. Bienaymé H. Wiley-VCH; Weinheim: 2005. 
    Google Scholar
  • 3h Dömling A. Chem. Rev.  2006,  106:  17 
    Google Scholar
  • 4 Hoffmann AW. Ann. Chem. Pharm.  1867,  144:  114 
    CrossrefGoogle Scholar
  • 5a Weber WP. Gokel GW. Ugi IK. Angew. Chem., Int. Ed. Engl.  1972,  11:  530 
    Google Scholar
  • 5b Gokel GW. Widera RP. Weber WP. Org Synth., Coll. Vol. VI  1988,  232 
    Google Scholar
  • 6a Ugi I. Meyr R. Chem. Ber.  1960,  93:  239 
    Google Scholar
  • 6b Ugi I. Fetzer U. Eholzer U. Knupper H. Offermann K. Angew. Chem., Int. Ed. Engl.  1965,  4:  472 ; Angew. Chem. 1965, 77, 492
    Google Scholar
  • 6c Ugi I. Meyr R. Lipinski M. Bodensheim F. Rosendahl F. Org. Synth., Coll. Vol. V  1973,  300 
    Google Scholar
  • 7a O’Neil IA. In Comprehensive Organic Functional Group Transformations   Vol 3:  Katrizky AR. Meth-Cohn D. Rees CW. Pergamon; Oxford: 1995.  p.693-726  
    Google Scholar
  • 7b Hoffman P. Gokel G. Marquading D. Ugi I. In Isonitrile Chemistry   Ugi I. Academic Press; New York: 1971.  p.9 
    Google Scholar
  • 7c Periasamy MP. Walborsky HM. Org. Prep. Proced. Int.  1979,  11:  293 ; and references cited therein
    Google Scholar
  • 8 Mukaiyama T. Nambu H. Okamoto M. J. Org. Chem.  1962,  27:  3651 
    CrossrefGoogle Scholar
  • 9 Makaiyama T. Masutani K. Minowa T. Chem. Lett.  2005,  34:  1124 
    CrossrefGoogle Scholar
  • 10a Schröder R. Schöllkopf U. Blume E. Hoppe I. Justus Liebigs Ann. Chem.  1975,  533 
    Google Scholar
  • 10b Whitney SE. Rickborn B. J. Org. Chem.  1991,  56:  3058 
    Google Scholar
  • 10c Pirrung MC. J. Am. Chem. Soc.  2006,  128:  11772 
    Google Scholar
  • 11a Gassman PG. Guggenheim TL. J. Am. Chem. Soc.  1982,  104:  5849 
    Google Scholar
  • 11b Imi K. Yanagihara N. Utimoto K. J. Org. Chem.  1987,  52:  1013 
    Google Scholar
  • 11c Onaka M. Ohta A. Sugita K. Izumi Y. Appl. Catal., A  1995,  125:  203 
    Google Scholar
  • 12a Gautier A. Justus Liebigs Ann. Chem.  1867,  142:  289 
    Google Scholar
  • 12b Gautier A. Ann. Chim. (Paris)  1869,  17:  103 
    Google Scholar
  • 12c Gautier A. Ann. Chim. (Paris)  1869,  17:  203 
    Google Scholar
  • 13 Jackson HL. McKusick BC. Org. Synth., Coll. Vol. IV  1963,  438 
    Google Scholar
  • 14 Heldt WZ. J. Org. Chem.  1961,  26:  2604 
    CrossrefGoogle Scholar
  • 15a Davis TL. Yelland WE. J. Am. Chem. Soc.  1937,  59:  1998 
    Google Scholar
  • 15b Carretero JC. Garcia Ruano JL. Tetrahedron Lett.  1985,  26:  3381 
    Google Scholar
  • 15c Kitano Y. Manoda T. Miura T. Chiba K. Tada M. Synthesis  2006,  405 
    Google Scholar
  • 16a Kitano Y. Chiba K. Tada M. Tetrahedron Lett.  1998,  39:  1911 
    Google Scholar
  • 16b Kitano Y. Nogata Y. Matsumara K. Yoshimura E. Chiba K. Tada M. Sakaguchi I. Tetrahedron  2005,  61:  9969 
    Google Scholar
  • 17a Grigg R. Lansdell MI. Thornton-Pett M. Tetrahedron  1999,  55:  2025 
    Google Scholar
  • 17b Bon RS. van Vliet B. Sprenkels NE. Schmitz RF. de Kanter FJJ. Stevens CV. Swart M. Bickelhaupt FM. Groen MB. Orru RVA. J. Org. Chem.  2005,  70:  3542 
    Google Scholar
  • 18a Songstad J. Stangeland LJ. Austad T. Acta Chem. Scand.  1970,  24:  355 
    Google Scholar
  • 18b Engemyr LB. Martinsen A. Songstad J. Acta Chem. Scand., Ser. A  1974,  28:  255 
    Google Scholar
  • 20a El Kaim L. Grimaud L. Oble J. Angew. Chem. Int. Ed.  2005,  117:  7961 
    Google Scholar
  • 20b El Kaim L. Gizolme M. Grimaud L. Oble J. J. Org. Chem.  2007,  72:  4169 
    Google Scholar
  • 20c Barthelon A. El Kaïm L. Gizolme M. Grimaud L. Eur. J. Org. Chem.  2008,  35:  5974 
    Google Scholar
  • 21 Dai W.-M. Li H. Tetrahedron  2007,  63:  12866 
    CrossrefGoogle Scholar
  • 22 Though a previous one-pot isocyanide synthesis-Ugi reaction sequence has been reported, the starting material was already a benzyl isocyanide which was alkylated under basic treatment: Tempest PA. Brown SD. Armstrong RW. Angew. Chem., Int. Ed. Engl.  1996,  35:  640 ; Angew. Chem. 1996, 108, 689
    Google Scholar
19

Even if these conditions seemed promising, iron salts were abandoned because we failed to perform the one-pot multicomponent couplings with them.