Synthesis 2010(5): 770-774  
DOI: 10.1055/s-0029-1218614
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

5-Amino-2-furylmethylamines - Appealing Precursors of Amino­isoindolinones?

Raouf Medimagha, Sylvain Marque*a, Damien Prima, Saber Chattib
a Université de Versailles Saint-Quentin-en-Yvelines, Institut Lavoisier de Versailles (ILV) UMR 8180, 45 Avenue des Etats-Unis, 78035 Versailles Cedex, France
Fax: +33(1)39254452; e-Mail: sylvain.marque@chimie.uvsq.fr;
b Institut National de Recherche et d’Analyse Physicochimique (INRAP), Pôle Technologique de Sidi Thabet, 2020 Sidi Thabet, Tunisia
Further Information

Publication History

Received 4 November 2009
Publication Date:
16 December 2009 (eFirst)

Abstract

Isoindolinones were constructed according to an original [4+2]-cycloaddition strategy. Unprecedented 5-amino-2-furyl­methylamines were prepared and revealed as efficient precursors of new aminoisoindolinones, obtained via a Diels-Alder and lactamization sequence.

    References

  • 1 Wada T. Fukuda N. Psychopharmacology  1991,  103:  314 
  • 2 Stuck TL. Assink BK. Bates RC. Erdman DT. Fedij V. Jennings SM. Lassig JA. Smith RJ. Smith TL. Org. Process Res. Dev.  2003,  7:  851 
  • 3 Valencia E. Freyer AJ. Shamma M. Fajardo V. Tetrahedron Lett.  1984,  25:  599 
  • 4 Alonso R. Castedo L. Dominguez D. Tetrahedron Lett.  1985,  26:  2925 
  • 5a Enders D. Braig V. Raabe G. Can. J. Chem.  2001,  79:  1528 
  • 5b Campbell JB. Dedinas RF. Trumbower-Walsh SA. J. Org. Chem.  1996,  61:  6205 
  • 6 Yao T. Larock RC. J. Org. Chem.  2005,  70:  1432 
  • 7a Ben-Othman R. Othman M. Coste S. Decroix B. Tetrahedron  2008,  64:  559 
  • 7b Othman M. Pigeon P. Decroix B. Tetrahedron  1998,  54:  8737 
  • 8 Chen M.-D. He M.-Z. Zhou X. Huang L.-Q. Ruan Y.-P. Huang P.-Q. Tetrahedron  2005,  61:  1335 
  • 9 Shen L. Hsung RP. Org. Lett.  2005,  7:  775 
  • 10a Perard-Viret J. Prangé T. Tomas A. Royer J. Tetrahedron  2002,  58:  5103 
  • 10b Deniau E. Enders D. Tetrahedron  2001,  57:  2581 
  • 10c Commins DL. Schilling S. Zhang Y. Org. Lett.  2005,  7:  95 
  • 10d Allin SM. Northfield CJ. Page MI. Slawin AMZ. Tetrahedron Lett.  1997,  38:  3627 
  • 10e Allin SM. Northfield CJ. Page MI. Slawin AMZ. Tetrahedron Lett.  1998,  39:  4905 
  • 10f Allin SM. Northfield CJ. Page MI. Slawin AMZ. Tetrahedron Lett.  1999,  40:  141 
  • 11a Prim D. Kirsch G. Nicoud J.-F. Synlett  1998,  383 
  • 11b Prim D. Kirsch G. Tetrahedron  1999,  55:  6511 
  • 11c Migianu E. Prim D. Kirsch G. Synlett  2000,  459 
  • 12 For a one-pot selective procedure using similar conditions, see: Terrasson V. Marque S. Scarpacci A. Prim D. Synthesis  2006,  1858 
  • 13 Medimagh R. Marque S. Prim D. Chatti S. Heterocycles  2009,  78:  679 
  • 15 Medimagh R. Marque S. Prim D. Chatti S. Zarrouk H. J. Org. Chem.  2008,  73:  2191 
  • 16 Medimagh R. Marque S. Prim D. Marrot J. Chatti S. Org. Lett.  2009,  11:  1817 
14

A sequence involving the reaction between 1 and 2 prior to the successive addition of NaBH4 and then 5 was first envisaged, but did not succeed; the sequence between 1 and 2, then 5, prior to the addition of NaBH4 gave a mixture of products.