Synthesis 2010(7): 1188-1194  
DOI: 10.1055/s-0029-1219233
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Bromine-Induced Facile Synthesis of Butenolides and Spirobutenolides from Sterically Congested Tetrasubstituted Dialkyl Alkylidene Succinates

Ramesh M. Patel, Narshinha P. Argade*
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India
Fax: +91(20)25902629; e-Mail: np.argade@ncl.res.in;
Further Information

Publication History

Received 26 November 2009
Publication Date:
20 January 2010 (eFirst)

Abstract

Starting from sterically congested tetrasubstituted dialkyl alkylidene succinates, facile general approach to several dialkyl substituted butenolides and spirobutenolides with the generation of quaternary carbon center has been demonstrated via bromine-induced dealkylative regioselective intramolecular cyclization and dehydrobromination pathway. The mechanistic aspects involved in the formation of butenolides have been also described in brief.

    References

  • 1a Rao YS. Chem. Rev.  1976,  76:  625 
  • 1b Avetisyan AA. Dangyan MT. Russ. Chem. Rev.  1977,  46:  643 
  • 1c Figadère B. Acc. Chem. Res.  1995,  28:  359 
  • 1d Braña MF. García ML. López B. de Pascual-Teresa B. Ramos A. Pozuelo JM. Domínguez MT. Org. Biomol. Chem.  2004,  2:  1864 
  • 1e Seitz M. Reiser O. Curr. Opin. Chem. Biol.  2005,  9:  285 
  • 2 Nauen R. Bretschneider T. Elbert A. Fischer R. Tiemann R. Pestic. Outlook  2003,  (December):  243 
  • 3a Jiang Y.-Q. Shi Y.-L. Shi M. J. Am. Chem. Soc.  2008,  130:  7202 
  • 3b Boukouvalas J. Loach RP. J. Org. Chem.  2008,  73:  8109 
  • 3c Boto A. Hernández D. Hernández R. J. Org. Chem.  2008,  73:  5287 
  • 3d Yamaguchi A. Matsunaga S. Shibasaki M. Org. Lett.  2008,  10:  2319 
  • 3e Lebel H. Parmentier M. Org. Lett.  2007,  9:  3563 
  • 4 Hyde AM. Buchwald SL. Org. Lett.  2009,  11:  2663 ; and references cited therein
  • 5a Geraghty NWA. Hernon EM. Tetrahedron Lett.  2009,  50:  570 
  • 5b Zhao Y.-M. Gu P. Tu Y.-Q. Fan C.-A. Zhang Q. Org. Lett.  2008,  10:  1763 
  • 5c Greco GE. Gleason BL. Lowery TA. Kier MJ. Hollander LB. Gibbs SA. Worthy AD. Org. Lett.  2007,  9:  3817 
  • 5d Ma S. Lu L. Lu P. J. Org. Chem.  2005,  70:  1063 
  • 5e Robertson J. Meo P. Dallimore JWP. Doyle BM. Hoarau C. Org. Lett.  2004,  6:  3861 
  • 5f Yoneda E. Kaneko T. Zhang S.-W. Onitsuka K. Takahashi S. Org. Lett.  2000,  2:  441 
  • 5g Harrowven DC. Hannam JC. Tetrahedron  1999,  55:  9341 
  • 6a Haval KP. Argade NP. J. Org. Chem.  2008,  73:  6936 
  • 6b Wakchaure PB. Easwar S. Puranik VG. Argade NP. Tetrahedron  2008,  64:  1786 
  • 6c Baag MM. Puranik VG. Argade NP. J. Org. Chem.  2007,  72:  1009 
  • 7 Thomas CJ. Wolak MA. Birge RR. Lees WJ. J. Org. Chem.  2001,  66:  1914 
  • 8a Gupta G. Banerjee S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1990,  29:  787 
  • 8b Asiri AM. Salem A.-JS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1999,  38:  488 
  • 8c Lee W.-WW. Gan L.-M. Loh T.-P. Synlett  2005,  2473 
  • 9 Paris J. Gouet E. Payard M. Reboul-Salze S. Hartmann L. Tronche P. Eur. J. Med. Chem.  1982,  17:  563 ; and references cited therein
  • 10 Ballini R. Bosica G. Damianl M. Righi P. Tetrahedron  1999,  55:  13451