N-Bromosuccinimide-Promoted Cyclization of β-Carboxymethyl Enamino Esters; Synthesis of Functionalized 4-Amino-2(5H)-Furanones

Abstract

An easy, two-step approach to various 5-carboxymethyl-2(5H)-furanones is described. A detailed study of the reaction of β-carboxymethyl enamino esters with N-bromosuccinimide is presented.

Key words

tetronamides - 4-amino-2(5H)-furanones - bromocyclization - alkylation - decarborxylation

References

• 1a Schlessinger RH. Yu YJ. J. Am. Chem. Soc.  1996,  118:  3301 
• 1b Clark JS. Marlin F. Nay B. Wilson C. Org. Lett.  2003,  5:  89 
• 1c Samaritani S. Bruyère H. Ballereau S. Royer J. C. R. Chim.  2005,  8:  841. 
• 1d Bruyère H. Dos Reis C. Samaritani S. Ballereau S. Royer J. Synthesis  2006,  1673 
• 2 For some example, see: Wang J. Jiang X. Chen M. Ge Z. Hu Y. Hu H. J. Chem. Soc., Perkin Trans. 1  2001,  66 
• 3 Greenhill JV. Ramli M. Tomassini T. J. Chem. Soc., Perkin Trans. 1  1975,  588 
• 4a Nishide K. Aramata A. Kamanaka T. Inoue T. Node M. Tetrahedron  1994,  50:  8337 
• 4b Dankwardt SM. Dankwardt JW. Schlessinger RH. Tetrahedron Lett.  1998,  39:  4971 
• 4c Dankwardt SM. Dankwardt JW. Schlessinger RH. Tetrahedron Lett.  1998,  39:  4975 
• 4d Dankwardt SM. Dankwardt JW. Schlessinger RH. Tetrahedron Lett.  1998,  39:  4979 
• 4e Bruyère H. Ballereau S. Selkti M. Royer J. Tetrahedron  2003,  59:  5879 
• 5a Farina F. Martin MV. Sanchez F. Synthesis  1983,  397 
• 5b Martin M. Mateo AI. Tetrahedron: Asymmetry  1994,  5:  1385 
• 5c Cunha S. Oliveira CC. Sabino JS.
  J. Braz. Chem. Soc.  2011,  22:  598 
• 6 Sydorenko N. Hsung RP. Saleh Darwish O. Hahn JM. Liu J. J. Org. Chem.  2004,  69:  6732 
• 7a Pevet I. Meyer C. Cossy J. Synlett  2003,  663 
• 7b Li YJ. Lee PT. Yang CM. Chang YK. Weng YC. Liu YH. Tetrahedron Lett.  2004,  45:  1865 
• 8 Alladoum J. Dechoux L. Tetrahedron Lett.  2005,  46:  8203 
• 9 Jähnisch K. Duczek W. J. Prakt. Chem.  1990,  332:  117 
• 10 Schlessinger RH. Pettus TRR. J. Org. Chem.  1994,  59:  3246 
• 11 Zhou LH. Yu XQ. Pu L. J. Org. Chem.  2009,  74:  2013 
• 12 Kim JM. Na JE. Kim JN. Tetrahedron Lett.  2003,  44:  6317 
• 13 Campos PJ. Arranz J. Rodriguez MA. Tetrahedron Lett.  1997,  38:  8397 
• 15 An initial approximation of the structure leads to a geometry that was first improved using molecular mechanics techniques (MM2) implemented in Chem3D 5.0, and the resulting structure was optimized by the semiempirical Hamiltonian AM1 then at the ab initio STO3G level in the GAMESS suite of programs. Schmidt MW. Baldridge KK. Boatz JA. Elbert ST. Gordon MS. Jensen JJ. Koseki S. Matsunaya N. Nguyen KA. Su S. Windus TL. Dupuis M. Montgomery JA. J. Comput. Chem.  1993,  14:  1347 
• 16a Boosen KJ. Helv. Chim. Acta  1977,  60:  1256 
• 16b Momose K. Toyooka N. Nishi T. Takeuchi Y. Heterocycles  1988,  27:  1907 

14

Data were obtained from reactions with less than 5% deviation