Synthesis 2011(16): 2549-2552  
DOI: 10.1055/s-0030-1260107
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Diazo-Transfer Reactions to 1,3-Dicarbonyl Compounds with Tosyl Azide

Marc Presset, Damien Mailhol, Yoann Coquerel*, Jean Rodriguez*
Institut des Sciences Moléculaires de Marseille, iSm2-UMR CNRS 6263, Aix-Marseille Université, Centre Saint-Jérôme, Service 531, 13397 Marseille Cedex 20, France
Fax: +33(4)91289187; e-Mail: [email protected]; e-Mail: [email protected];
Further Information

Publication History

Received 18 May 2011
Publication Date:
14 July 2011 (online)

Abstract

A practical protocol for the large-scale preparation of 2-diazo-1,3-dicarbonyl compounds is described by diazo-transfer reactions with tosyl azide followed by efficient chromatographic purifications on silica gel and/or alumina.

    References

  • For efforts to clarify the terminologies of MBFTs, see:
  • 1a Tietze LF. Beifuss U. Angew. Chem., Int. Ed. Eng.  1993,  32:  131 
  • 1b Tietze LF. Chem. Rev.  1996,  96:  115 
  • 1c Domino Reactions in Organic Synthesis   Tietze LF. Brasche G. Gericke KM. Wiley-VCH; Weinheim: 2006. 
  • 1d Multicomponent Reactions   Zhu J. Bienaymé H. Wiley-VCH; Weinheim: 2005. 
  • 1e Coquerel Y. Boddaert T. Presset M. Mailhol D. Rodriguez J. In Ideas in Chemistry and Molecular Sciences: Advances in Synthetic Chemistry   Pignataro B. Wiley-VCH; Weinheim: 2010.  Chap. 9. p.187 
  • Reviews:
  • 2a Bonne D. Coquerel Y. Constantieux T. Rodriguez J. Tetrahedron: Asymmetry  2010,  21:  1085 
  • 2b Sanchez Duque MM. Allais C. Isambert N. Contantieux T. Rodriguez J. In Topics in Heterocyclic Chemistry   23:  Orru RV. Springer-Verlag; Berlin: 2010.  p.227 
  • 3 Kirmse W. Eur. J. Org. Chem.  2002,  2193 
  • 4a Presset M. Coquerel Y. Rodriguez J. J. Org. Chem.  2009,  74:  415 
  • 4b Presset M. Coquerel Y. Rodriguez J. Org. Lett.  2009,  11:  5706 
  • 4c Presset M. Coquerel Y. Rodriguez J. Org. Lett.  2010,  12:  4212 
  • 4d Boddaert T. Coquerel Y. Rodriguez J. Chem. Eur. J.  2011,  17:  2048 
  • Reviews:
  • 5a Zhang Z. Wang J. Tetrahedron  2008,  64:  6577 
  • 5b Doyle MP. Ye T. McKervey MA. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds   Wiley; New York: 1998. 
  • 6 Maas G. Angew. Chem. Int. Ed.  2009,  48:  8186 
  • 7a Regitz M. Tetrahedron Lett.  1964,  1403 
  • 7b Regitz M. Angew. Chem., Int. Ed. Engl.  1967,  6:  733 
  • 7c Regitz M. Synthesis  1972,  351 
  • 7d Regitz M. Hocker J. Liedhegener A. Org. Synth. Coll. Vol. 5   Wiley; New York: 1973.  p.183 
  • 8 Explosive decompositions of TsN3 have been reported at temperatures above 120 ˚C in: Hazen GG. Weinstock LM. Connell R. Bollinger FW. Synth. Commun.  1981,  11:  947 
  • 9 Taber DF. Ruckle RE. Hennessy MJ. J. Org. Chem.  1986,  51:  4077 
  • 10 Baum JS. Shook DA. Davies HML. Smith HD. Synth. Commun.  1987,  17:  1709 
  • 11 Green GM. Peet NP. Metz WA. J. Org. Chem.  2001,  66:  2509 
  • 12 Goddard-Borger ED. Stick RV. Org. Lett.  2007,  9:  3797 
  • 13a Kitamura M. Tashiro N. Okauchi T. Synlett  2009,  2943 
  • 13b Kitamura M. Tashiro N. Miyagawa S. Okauchi T. Synthesis  2011,  1037 
  • 14 Chiang Y. Kresge AJ. Nikolaev VA. Popik VV.
    J. Am. Chem. Soc.  1997,  119:  11183 
  • 15 Oda M. Kasai M. Kitahara Y. Chem. Lett.  1977,  307 
  • 16 Popik VV. Korneev SM. Nikolaev VA. Korobitsyna IK. Synthesis  1991,  195 
  • 17 Davies JR. Kane PD. Moody CJ. Tetrahedron  2004,  60:  3967 
  • 18 Kokel B. Viehe HG. Angew. Chem., Int. Ed. Engl.  1980,  19:  716