Synthesis 2005(6): 977-985  
DOI: 10.1055/s-2005-861850
PAPER
© Georg Thieme Verlag Stuttgart · New York

Oxidative Free Radical Cyclization of 2-(Ethoxycarbonylmethyl)-1,4-naphthoquinone Derivatives

Hui-Li Chen, Chien-Yu Lin, Yu-Chih Cheng, An-I Tsai, Che-Ping Chuang*
Department of Chemistry, National Cheng Kung University, Tainan, Taiwan 70101
Fax: +88(66)2740552; e-Mail: [email protected];
Further Information

Publication History

Received 25 October 2004
Publication Date:
09 March 2005 (online)

Abstract

A manganese(III)-mediated oxidative free radical cyclization of 2-(ethoxycarbonylmethyl)-1,4-naphthoquinone derivatives is described. These starting 2-(ethoxycarbonylmethyl)-1,4-naphthoquinones can be synthesized effectively from the reaction of corresponding 1,4-naphthoquinones with ethyl nitroacetate. With 2-benzyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones, naphthacene-5,12-diones were produced effectively in high selectivity. With ethyl 2-benzoyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones, in addition to the expected 6-hydroxynaphthacene-5,12-diones, the novel naphtho[2,3-c]furan-4,9-diones were also formed as the major product.

    References

  • 1a Hart DJ. Science  1984,  223:  883 
  • 1b Neumann WP. Synthesis  1987,  665 
  • 1c Curran DP. Synthesis  1988,  417 
  • 1d Curran DP. Synthesis  1988,  489 
  • 1e Giese B. Kopping B. Göbel T. Dickhaut J. Thoma G. Kulicke KJ. Trach F. Org. React.  1996,  49:  301 
  • 1f Bowman WR. Bridge CF. Brookes P. J. Chem. Soc., Perkin Trans. 1  2000, 
  • 1g Zheng W. Tetrahedron  2001,  57:  7237 
  • 2a Melikyan GG. Synthesis  1993,  833 
  • 2b Iqbal J. Bhatia B. Nayyar NK. Chem. Rev.  1994,  94:  519 
  • 2c Snider BB. Chem. Rev.  1996,  96:  3391 
  • 2d Nair V. Panicker SB. Nair LG. George TG. Augustine A. Synlett  2003,  156 
  • 2e Nair V. Balagopal L. Rajan R. Mathew J. Acc. Chem. Rev.  2004,  37:  21 
  • 3a Kuntsmann MP. Mitscher LA. J. Org. Chem.  1966,  31:  2920 
  • 3b Maehr H. Liu C.-M. Perrotta A. Smallheer JM. Williams TH. Blount JF. J. Antibiot.  1982,  35:  1627 
  • 3c Hayakawa Y. Furihata K. Seto H. Otake N. Tetrahedron Lett.  1985,  26:  3471 
  • 3d Hayakawa Y. Furihata K. Seto H. Otake N. Tetrahedron Lett.  1985,  26:  3475 
  • 4a The Chemistry of The Quinoid Compounds   Patai S. Rappoport Z. Wiley; New York: 1988. 
  • 4b Thomson RH. Natural Occurring Quinones IV: Recent Advances   Chapman & Hall; London: 1997. 
  • 5a Citterio A. Sebastiano R. Carvayal MC. J. Org. Chem.  1991,  56:  5335 
  • 5b Cho I.-S. Muchowski JM. Synthesis  1991,  567 
  • 5c Citterio A. Sebastiano R. Nicolini M. Tetrahedron  1993,  49:  7743 
  • 5d Tanyeli C. Özdenirhen D. Sezen B. Tetrahedron  2002,  58:  9983 
  • 6a Chuang C.-P. Wang S.-F. Tetrahedron Lett.  1994,  35:  4365 
  • 6b Chuang C.-P. Wang S.-F. J. Chin. Chem. Soc.  1997,  44:  271 ; Chem. Abstr. 1997, 127, 190631t
  • 6c Chuang C.-P. Wang S.-F. Tetrahedron  1998,  54:  10043 
  • 6d Chuang C.-P. Wang S.-F. Heterocycles  1999,  50:  489 
  • 6e Chuang C.-P. Wu Y.-L. Jiang M.-C. Tetrahedron  1999,  55:  11229 
  • 6f Jiang M.-C. Chuang C.-P. J. Org. Chem.  2000,  65:  5409 
  • 6g Wu Y.-L. Chuang C.-P. Lin P.-Y. Tetrahedron  2001,  57:  5543 
  • 6h Tsai A.-I. Wu Y.-L. Chuang C.-P. Tetrahedron  2001,  57:  7829 
  • 6i Tseng C.-C. Wu Y.-L. Chuang C.-P. Tetrahedron  2002,  57:  7625 
  • 7a Jacobsen N. Torsell K. Acta Chem. Scand.  1973,  27:  3211 
  • 7b Brown PM. Thomson RH. J. Chem. Soc., Perkin Trans. 1  1976,  997 
  • 7c Citterio A. Arnoldi A. Minisci F. J. Org. Chem.  1979,  44:  2674 
  • 7d Citterio A. Vismara E. Bernardi R. J. Chem. Res., Synop.  1983,  88 
  • 7e Citterio A. Vismara E. Bernardi R. J. Chem. Res., Miniprint  1983,  876 
  • 7f William DR. Clark MP. Tetrahedron Lett.  1998,  39:  7629 
  • 8 Aldersley MF. Chishti SH. Dean FM. Douglas ME. Ennis DS. J. Chem. Soc., Perkin Trans. 1  1990,  2163