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Synthesis 2011(17): 2781-2788
DOI: 10.1055/s-0030-1260132
DOI: 10.1055/s-0030-1260132
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkN-Bromosuccinimide-Promoted Cyclization of β-Carboxymethyl Enamino Esters; Synthesis of Functionalized 4-Amino-2(5H)-Furanones
Further Information
Received
6 April 2011
Publication Date:
21 July 2011 (online)
Publication History
Publication Date:
21 July 2011 (online)

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
- 1a
Schlessinger RH.Yu YJ. J. Am. Chem. Soc. 1996, 118: 3301Reference Ris Wihthout Link - 1b
Clark JS.Marlin F.Nay B.Wilson C. Org. Lett. 2003, 5: 89Reference Ris Wihthout Link - 1c
Samaritani S.Bruyère H.Ballereau S.Royer J. C. R. Chim. 2005, 8: 841.Reference Ris Wihthout Link - 1d
Bruyère H.Dos Reis C.Samaritani S.Ballereau S.Royer J. Synthesis 2006, 1673Reference Ris Wihthout Link - 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: 8337Reference Ris Wihthout Link - 4b
Dankwardt SM.Dankwardt JW.Schlessinger RH. Tetrahedron Lett. 1998, 39: 4971Reference Ris Wihthout Link - 4c
Dankwardt SM.Dankwardt JW.Schlessinger RH. Tetrahedron Lett. 1998, 39: 4975Reference Ris Wihthout Link - 4d
Dankwardt SM.Dankwardt JW.Schlessinger RH. Tetrahedron Lett. 1998, 39: 4979Reference Ris Wihthout Link - 4e
Bruyère H.Ballereau S.Selkti M.Royer J. Tetrahedron 2003, 59: 5879Reference Ris Wihthout Link - 5a
Farina F.Martin MV.Sanchez F. Synthesis 1983, 397Reference Ris Wihthout Link - 5b
Martin M.Mateo AI. Tetrahedron: Asymmetry 1994, 5: 1385Reference Ris Wihthout Link - 5c
Cunha S.Oliveira CC.Sabino JS.
J. Braz. Chem. Soc. 2011, 22: 598Reference Ris Wihthout Link - 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, 663Reference Ris Wihthout Link - 7b
Li YJ.Lee PT.Yang CM.Chang YK.Weng YC.Liu YH. Tetrahedron Lett. 2004, 45: 1865Reference Ris Wihthout Link - 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: 1256Reference Ris Wihthout Link - 16b
Momose K.Toyooka N.Nishi T.Takeuchi Y. Heterocycles 1988, 27: 1907Reference Ris Wihthout Link
References
Data were obtained from reactions with less than 5% deviation