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Synthesis 2003(5): 0673-0676
DOI: 10.1055/s-2003-38066
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 1H-2-Benzopyran-5,8-dione Derivatives from 2-(1-Hydroxy­alkyl)-1,4-benzoquinones and Enamines

Kazuhiro Kobayashi*, Kosaku Nomura, Toshikazu Ogata, Miyuki Tanmatsu, Osamu Morikawa, Hisatoshi Konishi
Department of Materials Science, Faculty of Engineering, Tottori University, Koyama-minami, Tottori 680-8552, Japan
Fax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp;
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Publication History

Received 28 November 2002
Publication Date:
21 March 2003 (online)

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Abstract

An efficient synthesis of the title benzopyranodione derivatives based on a Michael addition/cyclization sequence between 2-(1-hydroxyalkyl)-1,4-benzoquinones and enamines (or an imine) is described.

Key words

enamines - heterocycles - benzoquinones

    References

  • 1a Kobayashi K. Uchida M. Uneda T. Tanmatsu M. Morikawa O. Konishi H. Tetrahedron Lett.  1998,  39:  7725 
    CrossrefGoogle Scholar
  • 1b Kobayashi K. Uchida M. Uneda T. Yoneda K. Tanmatsu M. Morikawa O. Konishi H. J. Chem. Soc., Perkin Trans 1  2001,  2977 
    CrossrefGoogle Scholar
  • 2a Kobayashi K. Uneda T. Kawakita M. Morikawa O. Konishi H. Tetrahedron Lett.  1997,  38:  837 
    Google Scholar
  • 2b Kobayashi K. Tanaka K. Uneda T. Maeda M. Morikawa O. Konishi H. Synthesis  1998,  1243 
    Google Scholar
  • 2c Kobayashi K. Taki T. Kawakita M. Uchida M. Morikawa O. Konishi H. Heterocycles  1999,  51:  349 
    Google Scholar
  • 2d Kobayashi K. Furuta Y. Matsuoka H. Uchida M. Morikawa O. Konishi H. Chem. Lett.  1999,  503 
    Google Scholar
  • 2e Kobayashi K. Takanohashi A. Watanabe S. Morikawa O. Konishi H. Tetrahedron Lett.  2000,  41:  7657 
    Google Scholar
  • 2f Tanaka K. Takanohashi A. Morikawa O. Konishi H. Kobayashi K. Heterocycles  2001,  55:  1561 
    Google Scholar
  • 2g Kobayashi K. Yoneda K. Uchida M. Matsuoka H. Morikawa O. Konishi H. Heterocycles  2001,  55:  2423 
    Google Scholar
  • 3 Garner P. Anderson JT. Turske RA. Chem. Commun.  2000,  1579 
    CrossrefGoogle Scholar
  • 4 Stevens RV. Vinogradoff AP. J. Org. Chem.  1985,  50:  4056 
    Google Scholar
  • For previous syntheses, see:
  • 5a Retamal JI. Ruiz VN. Tapia RA. Valderrama JA. Vega JC. Synth. Commun.  1982,  12:  279 
    CrossrefGoogle Scholar
  • 5b Giles RGF. Green IR. Pestatna JAX. J. Chem. Soc., Perkin Trans. 1  1984,  2389 
    CrossrefGoogle Scholar
  • 5c Green IR. Hugo VI. Oosthuisen FJ. van Eeden N. Giles RGF. S. Afr. J. Chem.  1995,  48:  15 ; Chem. Abstr. 1996, 124 , 260773e
    CrossrefGoogle Scholar
  • 5d Esterhuyse AJ. Hugo VI. Pestatna JAX. Snijman PW. Green IR. S. Afr. J. Chem.  1993,  46:  34 ; Chem. Abstr. 1994, 120, 244537t
    CrossrefGoogle Scholar
  • 5e Xiong Y. Xia H. Moore HW. J. Org. Chem.  1995,  60:  6460 
    CrossrefGoogle Scholar
  • 5f de Koning CB. Green IR. Michael JP. Oliveira JR. Tetrahedron Lett.  1997,  38:  5055 
    CrossrefGoogle Scholar
  • 5g Green IR. de Koning CB. Hugo VI. S. Afr. J. Chem.  1999,  52:  112 ; Chem. Abstr. 2000, 132 , 264944r
    CrossrefGoogle Scholar
  • 5h Giles RGF. Joll CA. J. Chem. Soc., Perkin Trans. 1  1999,  3039 
    CrossrefGoogle Scholar
  • 5i Valderrama JA. Pessoa-Mahama D. Tapia RA. de Arias AR. Nakayama H. Torres S. Miret J. Ferreira ME. Tetrahedron  2001,  57:  8653 
    CrossrefGoogle Scholar
  • 6a Kometani T. J. Chem. Soc., Perkin Trans. 1  1981,  1191 
    CrossrefGoogle Scholar
  • 6b Attardo G, Xu YC, Lavallée JF, Rej R, and Belleau B. inventors; PCT Int. Patent  19725.  ; Chem. Abstr. 1992, 117, 27052q
    Crossref
  • 6c Lavallée JF. Rej R. Courchesne M. Nguyen D. Attardo G. Tetrahedron Lett.  1993,  34:  3519 
    CrossrefGoogle Scholar
  • 6d Xu YC. Lebeau E. Attardo G. Mters PL. Gillard JW. J. Org. Chem.  1994,  59:  4868 
    CrossrefGoogle Scholar
  • 6e Attardo G, Breining T, Courchesne M, Kraus JL, Lamothe S, Lavallée JF, Lebeau E, Nguyen D, and Rej R. inventors; PCT Int. Patent  11382.  ; Chem. Abstr. 1996, 124, 30252e
    Crossref
  • 6f Toedter C. Lackner H. Liebigs Ann. Chem.  1996,  1385 
    CrossrefGoogle Scholar
  • 6g Attardo G, Kraus JL, Courchesne M, Lamothe S, Lavallée JF, Lebeau E, Nguyen D, Rej R, St-Denis Y, Wang W, Xu YC, Barbeau F, and Belleau B. inventors; US Patent  5593970.  ; Chem. Abstr. 1997, 126; 199791g
    Crossref
  • 6h Donner CD. Gill M. Tetrahedron Lett.  1999,  40:  3921 
    CrossrefGoogle Scholar
  • 6i Giles RGF. Green IR. Oosthuizen FJ. Taylor CP. Tetrahedron Lett.  2001,  42:  5753 
    CrossrefGoogle Scholar
  • 8 Stork G. Brizzolara A. Landesman H. Szmuszkovicz J. Terrell R. J. Am. Chem. Soc.  1963,  85:  207 
    CrossrefGoogle Scholar
  • 9 Bunnelle WH. Singam PR. Narayanan BA. Bradshaw CW. Liou TS. Synthesis  1997,  439 
    Article in Thieme ConnectGoogle Scholar
  • 10 Kessar SV. Gupta YP. Mohammad T. Goyal M. Sawal KK. J. Chem. Soc., Chem. Commun.  1983,  400 
    CrossrefGoogle Scholar
  • 11 Cason J. Org. React.  1948,  4:  305 
    Google Scholar
7

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