Synthesis, Table of Contents 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 KonishiDepartment of Materials Science, Faculty of Engineering, Tottori University, Koyama-minami, Tottori 680-8552, JapanFax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp; Recommend Article Abstract Buy Article All articles of this category 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 Full Text References References 1a Kobayashi K. Uchida M. Uneda T. Tanmatsu M. Morikawa O. Konishi H. Tetrahedron Lett. 1998, 39: 7725 1b Kobayashi K. Uchida M. Uneda T. Yoneda K. Tanmatsu M. Morikawa O. Konishi H. J. Chem. Soc., Perkin Trans 1 2001, 2977 2a Kobayashi K. Uneda T. Kawakita M. Morikawa O. Konishi H. Tetrahedron Lett. 1997, 38: 837 2b Kobayashi K. Tanaka K. Uneda T. Maeda M. Morikawa O. Konishi H. Synthesis 1998, 1243 2c Kobayashi K. Taki T. Kawakita M. Uchida M. Morikawa O. Konishi H. Heterocycles 1999, 51: 349 2d Kobayashi K. Furuta Y. Matsuoka H. Uchida M. Morikawa O. Konishi H. Chem. Lett. 1999, 503 2e Kobayashi K. Takanohashi A. Watanabe S. Morikawa O. Konishi H. Tetrahedron Lett. 2000, 41: 7657 2f Tanaka K. Takanohashi A. Morikawa O. Konishi H. Kobayashi K. Heterocycles 2001, 55: 1561 2g Kobayashi K. Yoneda K. Uchida M. Matsuoka H. Morikawa O. Konishi H. Heterocycles 2001, 55: 2423 3 Garner P. Anderson JT. Turske RA. Chem. Commun. 2000, 1579 4 Stevens RV. Vinogradoff AP. J. Org. Chem. 1985, 50: 4056 For previous syntheses, see: 5a Retamal JI. Ruiz VN. Tapia RA. Valderrama JA. Vega JC. Synth. Commun. 1982, 12: 279 5b Giles RGF. Green IR. Pestatna JAX. J. Chem. Soc., Perkin Trans. 1 1984, 2389 5c Green IR. Hugo VI. Oosthuisen FJ. van Eeden N. Giles RGF. S. Afr. J. Chem. 1995, 48: 15 ; Chem. Abstr. 1996, 124 , 260773e 5d Esterhuyse AJ. Hugo VI. Pestatna JAX. Snijman PW. Green IR. S. Afr. J. Chem. 1993, 46: 34 ; Chem. Abstr. 1994, 120, 244537t 5e Xiong Y. Xia H. Moore HW. J. Org. Chem. 1995, 60: 6460 5f de Koning CB. Green IR. Michael JP. Oliveira JR. Tetrahedron Lett. 1997, 38: 5055 5g Green IR. de Koning CB. Hugo VI. S. Afr. J. Chem. 1999, 52: 112 ; Chem. Abstr. 2000, 132 , 264944r 5h Giles RGF. Joll CA. J. Chem. Soc., Perkin Trans. 1 1999, 3039 5i Valderrama JA. Pessoa-Mahama D. Tapia RA. de Arias AR. Nakayama H. Torres S. Miret J. Ferreira ME. Tetrahedron 2001, 57: 8653 6a Kometani T. J. Chem. Soc., Perkin Trans. 1 1981, 1191 6b Attardo G, Xu YC, Lavallée JF, Rej R, and Belleau B. inventors; PCT Int. Patent 19725. ; Chem. Abstr. 1992, 117, 27052q 6c Lavallée JF. Rej R. Courchesne M. Nguyen D. Attardo G. Tetrahedron Lett. 1993, 34: 3519 6d Xu YC. Lebeau E. Attardo G. Mters PL. Gillard JW. J. Org. Chem. 1994, 59: 4868 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 6f Toedter C. Lackner H. Liebigs Ann. Chem. 1996, 1385 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 6h Donner CD. Gill M. Tetrahedron Lett. 1999, 40: 3921 6i Giles RGF. Green IR. Oosthuizen FJ. Taylor CP. Tetrahedron Lett. 2001, 42: 5753 7 The reaction in toluene proceeded sluggishly and gave a lower yield of the expected product. 8 Stork G. Brizzolara A. Landesman H. Szmuszkovicz J. Terrell R. J. Am. Chem. Soc. 1963, 85: 207 9 Bunnelle WH. Singam PR. Narayanan BA. Bradshaw CW. Liou TS. Synthesis 1997, 439 10 Kessar SV. Gupta YP. Mohammad T. Goyal M. Sawal KK. J. Chem. Soc., Chem. Commun. 1983, 400 11 Cason J. Org. React. 1948, 4: 305
