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Volumn 71, Issue 7, 1998, Pages 1691-1697

One-Step Synthesis of Naphthofurandione, Benzofurandione, and Phenalenofuranone Derivatives by the CAN-Mediated Cycloaddition

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EID: 0001748898     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.1691     Document Type: Article
Times cited : (24)

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    • For recent reports on the one-pot construction of naphthofurandione and benzofurandione skeletons: a) K. Kobayashi, H. Shimizu, A. Sasaki, and H. Suginome, J. Org. Chem., 58, 4614 (1993); b) K. Kobayashi, Y. Kanno, and H. Suginome, J. Chem. Soc., Perkin Trans. 1, 1993, 1449; c) T. Shu, D.-W. Chen, and M. Ochiai, Tetrahedron Lett., 37, 5539 (1996); d) K. Kobayashi, T. Uneda, M. Kawakita, O. Morikawa, and H. Konishi, Tetrahedron Lett., 38, 837 (1997).
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    • For recent reports on the utilization of these hydroxyquinones in the preparation of heterocycle-fused quinones: A. B. de Oliveira, D. T. Ferreira, and D. S. Raslan, Tetrahedron Lett., 29, 155 (1988); L. Kopanski, D. Karbach, G. Selbutschka, and W. Steglich, Liebigs Ann. Chem., 1987, 793; C. B. Saitz, J. A. Valderrama, and R. Tapia, Synth. Commun., 20, 3103 (1990).
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    • For recent reports on the utilization of these hydroxyquinones in the preparation of heterocycle-fused quinones: A. B. de Oliveira, D. T. Ferreira, and D. S. Raslan, Tetrahedron Lett., 29, 155 (1988); L. Kopanski, D. Karbach, G. Selbutschka, and W. Steglich, Liebigs Ann. Chem., 1987, 793; C. B. Saitz, J. A. Valderrama, and R. Tapia, Synth. Commun., 20, 3103 (1990).
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    • For recent reports on the utilization of these hydroxyquinones in the preparation of heterocycle-fused quinones: A. B. de Oliveira, D. T. Ferreira, and D. S. Raslan, Tetrahedron Lett., 29, 155 (1988); L. Kopanski, D. Karbach, G. Selbutschka, and W. Steglich, Liebigs Ann. Chem., 1987, 793; C. B. Saitz, J. A. Valderrama, and R. Tapia, Synth. Commun., 20, 3103 (1990).
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    • For metal-mediated cycloaddition reactions of 1,3-dicarbonyls to alkenes forming 1,2-dihydrofuran derivatives, see: K. Ichikawa, S. Uemura, and T. Sugita, Tetrahedron, 22, 407 (1966); E. I. Heiba and R. M. Dessau, J. Org. Chem., 39, 3456 (1974); M. G. Vinogradov, A. E. Kondorsky, and G. I. Nikishin, Synthesis, 1988, 60; E. Baciocchi and R. Ruzziconi, Synth. Commun., 18, 1841 (1988), and references cited therein. For recent reports, see: J. M. Mellor and S. Mohammed, Tetrahedron Lett., 32, 7111 (1991); V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1995, 187; 1995, 1881; 1996, 1487; Y. R. Lee and B. S. Kim, Tetrahedron Lett., 38, 2095 (1997); Y. R. Lee, N. S. Kim, and B. S. Kim, Tetrahedron Lett., 38, 5671 (1997). See also: J. Iqbal and M. Mukhopadhyay, Synlett, 1997, 876. For other approaches to the formation of dihydrofuran rings, see: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986); H. Hagiwara, K. Kato, T. Suzuki, and M. Ando, Tetrahedron Lett., 38, 2103 (1997).
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    • For metal-mediated cycloaddition reactions of 1,3-dicarbonyls to alkenes forming 1,2-dihydrofuran derivatives, see: K. Ichikawa, S. Uemura, and T. Sugita, Tetrahedron, 22, 407 (1966); E. I. Heiba and R. M. Dessau, J. Org. Chem., 39, 3456 (1974); M. G. Vinogradov, A. E. Kondorsky, and G. I. Nikishin, Synthesis, 1988, 60; E. Baciocchi and R. Ruzziconi, Synth. Commun., 18, 1841 (1988), and references cited therein. For recent reports, see: J. M. Mellor and S. Mohammed, Tetrahedron Lett., 32, 7111 (1991); V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1995, 187; 1995, 1881; 1996, 1487; Y. R. Lee and B. S. Kim, Tetrahedron Lett., 38, 2095 (1997); Y. R. Lee, N. S. Kim, and B. S. Kim, Tetrahedron Lett., 38, 5671 (1997). See also: J. Iqbal and M. Mukhopadhyay, Synlett, 1997, 876. For other approaches to the formation of dihydrofuran rings, see: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986); H. Hagiwara, K. Kato, T. Suzuki, and M. Ando, Tetrahedron Lett., 38, 2103 (1997).
    • (1974) J. Org. Chem. , vol.39 , pp. 3456
    • Heiba, E.I.1    Dessau, R.M.2
  • 26
    • 0042017464 scopus 로고    scopus 로고
    • For metal-mediated cycloaddition reactions of 1,3-dicarbonyls to alkenes forming 1,2-dihydrofuran derivatives, see: K. Ichikawa, S. Uemura, and T. Sugita, Tetrahedron, 22, 407 (1966); E. I. Heiba and R. M. Dessau, J. Org. Chem., 39, 3456 (1974); M. G. Vinogradov, A. E. Kondorsky, and G. I. Nikishin, Synthesis, 1988, 60; E. Baciocchi and R. Ruzziconi, Synth. Commun., 18, 1841 (1988), and references cited therein. For recent reports, see: J. M. Mellor and S. Mohammed, Tetrahedron Lett., 32, 7111 (1991); V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1995, 187; 1995, 1881; 1996, 1487; Y. R. Lee and B. S. Kim, Tetrahedron Lett., 38, 2095 (1997); Y. R. Lee, N. S. Kim, and B. S. Kim, Tetrahedron Lett., 38, 5671 (1997). See also: J. Iqbal and M. Mukhopadhyay, Synlett, 1997, 876. For other approaches to the formation of dihydrofuran rings, see: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986); H. Hagiwara, K. Kato, T. Suzuki, and M. Ando, Tetrahedron Lett., 38, 2103 (1997).
    • Synthesis , vol.1988 , pp. 60
    • Vinogradov, M.G.1    Kondorsky, A.E.2    Nikishin, G.I.3
  • 27
    • 0001659803 scopus 로고
    • For metal-mediated cycloaddition reactions of 1,3-dicarbonyls to alkenes forming 1,2-dihydrofuran derivatives, see: K. Ichikawa, S. Uemura, and T. Sugita, Tetrahedron, 22, 407 (1966); E. I. Heiba and R. M. Dessau, J. Org. Chem., 39, 3456 (1974); M. G. Vinogradov, A. E. Kondorsky, and G. I. Nikishin, Synthesis, 1988, 60; E. Baciocchi and R. Ruzziconi, Synth. Commun., 18, 1841 (1988), and references cited therein. For recent reports, see: J. M. Mellor and S. Mohammed, Tetrahedron Lett., 32, 7111 (1991); V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1995, 187; 1995, 1881; 1996, 1487; Y. R. Lee and B. S. Kim, Tetrahedron Lett., 38, 2095 (1997); Y. R. Lee, N. S. Kim, and B. S. Kim, Tetrahedron Lett., 38, 5671 (1997). See also: J. Iqbal and M. Mukhopadhyay, Synlett, 1997, 876. For other approaches to the formation of dihydrofuran rings, see: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986); H. Hagiwara, K. Kato, T. Suzuki, and M. Ando, Tetrahedron Lett., 38, 2103 (1997).
    • (1988) Synth. Commun. , vol.18 , pp. 1841
    • Baciocchi, E.1    Ruzziconi, R.2
  • 28
    • 0026043108 scopus 로고
    • For metal-mediated cycloaddition reactions of 1,3-dicarbonyls to alkenes forming 1,2-dihydrofuran derivatives, see: K. Ichikawa, S. Uemura, and T. Sugita, Tetrahedron, 22, 407 (1966); E. I. Heiba and R. M. Dessau, J. Org. Chem., 39, 3456 (1974); M. G. Vinogradov, A. E. Kondorsky, and G. I. Nikishin, Synthesis, 1988, 60; E. Baciocchi and R. Ruzziconi, Synth. Commun., 18, 1841 (1988), and references cited therein. For recent reports, see: J. M. Mellor and S. Mohammed, Tetrahedron Lett., 32, 7111 (1991); V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1995, 187; 1995, 1881; 1996, 1487; Y. R. Lee and B. S. Kim, Tetrahedron Lett., 38, 2095 (1997); Y. R. Lee, N. S. Kim, and B. S. Kim, Tetrahedron Lett., 38, 5671 (1997). See also: J. Iqbal and M. Mukhopadhyay, Synlett, 1997, 876. For other approaches to the formation of dihydrofuran rings, see: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986); H. Hagiwara, K. Kato, T. Suzuki, and M. Ando, Tetrahedron Lett., 38, 2103 (1997).
    • (1991) Tetrahedron Lett. , vol.32 , pp. 7111
    • Mellor, J.M.1    Mohammed, S.2
  • 29
    • 0042017464 scopus 로고    scopus 로고
    • For metal-mediated cycloaddition reactions of 1,3-dicarbonyls to alkenes forming 1,2-dihydrofuran derivatives, see: K. Ichikawa, S. Uemura, and T. Sugita, Tetrahedron, 22, 407 (1966); E. I. Heiba and R. M. Dessau, J. Org. Chem., 39, 3456 (1974); M. G. Vinogradov, A. E. Kondorsky, and G. I. Nikishin, Synthesis, 1988, 60; E. Baciocchi and R. Ruzziconi, Synth. Commun., 18, 1841 (1988), and references cited therein. For recent reports, see: J. M. Mellor and S. Mohammed, Tetrahedron Lett., 32, 7111 (1991); V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1995, 187; 1995, 1881; 1996, 1487; Y. R. Lee and B. S. Kim, Tetrahedron Lett., 38, 2095 (1997); Y. R. Lee, N. S. Kim, and B. S. Kim, Tetrahedron Lett., 38, 5671 (1997). See also: J. Iqbal and M. Mukhopadhyay, Synlett, 1997, 876. For other approaches to the formation of dihydrofuran rings, see: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986); H. Hagiwara, K. Kato, T. Suzuki, and M. Ando, Tetrahedron Lett., 38, 2103 (1997).
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    • Nair, V.1    Matthew, J.2
  • 30
    • 0042017464 scopus 로고    scopus 로고
    • For metal-mediated cycloaddition reactions of 1,3-dicarbonyls to alkenes forming 1,2-dihydrofuran derivatives, see: K. Ichikawa, S. Uemura, and T. Sugita, Tetrahedron, 22, 407 (1966); E. I. Heiba and R. M. Dessau, J. Org. Chem., 39, 3456 (1974); M. G. Vinogradov, A. E. Kondorsky, and G. I. Nikishin, Synthesis, 1988, 60; E. Baciocchi and R. Ruzziconi, Synth. Commun., 18, 1841 (1988), and references cited therein. For recent reports, see: J. M. Mellor and S. Mohammed, Tetrahedron Lett., 32, 7111 (1991); V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1995, 187; 1995, 1881; 1996, 1487; Y. R. Lee and B. S. Kim, Tetrahedron Lett., 38, 2095 (1997); Y. R. Lee, N. S. Kim, and B. S. Kim, Tetrahedron Lett., 38, 5671 (1997). See also: J. Iqbal and M. Mukhopadhyay, Synlett, 1997, 876. For other approaches to the formation of dihydrofuran rings, see: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986); H. Hagiwara, K. Kato, T. Suzuki, and M. Ando, Tetrahedron Lett., 38, 2103 (1997).
    • J. Chem. Soc., Perkin Trans. 1 , vol.1995 , pp. 1881
  • 31
    • 0042017464 scopus 로고    scopus 로고
    • For metal-mediated cycloaddition reactions of 1,3-dicarbonyls to alkenes forming 1,2-dihydrofuran derivatives, see: K. Ichikawa, S. Uemura, and T. Sugita, Tetrahedron, 22, 407 (1966); E. I. Heiba and R. M. Dessau, J. Org. Chem., 39, 3456 (1974); M. G. Vinogradov, A. E. Kondorsky, and G. I. Nikishin, Synthesis, 1988, 60; E. Baciocchi and R. Ruzziconi, Synth. Commun., 18, 1841 (1988), and references cited therein. For recent reports, see: J. M. Mellor and S. Mohammed, Tetrahedron Lett., 32, 7111 (1991); V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1995, 187; 1995, 1881; 1996, 1487; Y. R. Lee and B. S. Kim, Tetrahedron Lett., 38, 2095 (1997); Y. R. Lee, N. S. Kim, and B. S. Kim, Tetrahedron Lett., 38, 5671 (1997). See also: J. Iqbal and M. Mukhopadhyay, Synlett, 1997, 876. For other approaches to the formation of dihydrofuran rings, see: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986); H. Hagiwara, K. Kato, T. Suzuki, and M. Ando, Tetrahedron Lett., 38, 2103 (1997).
    • J. Chem. Soc., Perkin Trans. 1 , vol.1996 , pp. 1487
  • 32
    • 0031585080 scopus 로고    scopus 로고
    • For metal-mediated cycloaddition reactions of 1,3-dicarbonyls to alkenes forming 1,2-dihydrofuran derivatives, see: K. Ichikawa, S. Uemura, and T. Sugita, Tetrahedron, 22, 407 (1966); E. I. Heiba and R. M. Dessau, J. Org. Chem., 39, 3456 (1974); M. G. Vinogradov, A. E. Kondorsky, and G. I. Nikishin, Synthesis, 1988, 60; E. Baciocchi and R. Ruzziconi, Synth. Commun., 18, 1841 (1988), and references cited therein. For recent reports, see: J. M. Mellor and S. Mohammed, Tetrahedron Lett., 32, 7111 (1991); V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1995, 187; 1995, 1881; 1996, 1487; Y. R. Lee and B. S. Kim, Tetrahedron Lett., 38, 2095 (1997); Y. R. Lee, N. S. Kim, and B. S. Kim, Tetrahedron Lett., 38, 5671 (1997). See also: J. Iqbal and M. Mukhopadhyay, Synlett, 1997, 876. For other approaches to the formation of dihydrofuran rings, see: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986); H. Hagiwara, K. Kato, T. Suzuki, and M. Ando, Tetrahedron Lett., 38, 2103 (1997).
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    • Lee, Y.R.1    Kim, B.S.2
  • 33
    • 0342894683 scopus 로고    scopus 로고
    • For metal-mediated cycloaddition reactions of 1,3-dicarbonyls to alkenes forming 1,2-dihydrofuran derivatives, see: K. Ichikawa, S. Uemura, and T. Sugita, Tetrahedron, 22, 407 (1966); E. I. Heiba and R. M. Dessau, J. Org. Chem., 39, 3456 (1974); M. G. Vinogradov, A. E. Kondorsky, and G. I. Nikishin, Synthesis, 1988, 60; E. Baciocchi and R. Ruzziconi, Synth. Commun., 18, 1841 (1988), and references cited therein. For recent reports, see: J. M. Mellor and S. Mohammed, Tetrahedron Lett., 32, 7111 (1991); V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1995, 187; 1995, 1881; 1996, 1487; Y. R. Lee and B. S. Kim, Tetrahedron Lett., 38, 2095 (1997); Y. R. Lee, N. S. Kim, and B. S. Kim, Tetrahedron Lett., 38, 5671 (1997). See also: J. Iqbal and M. Mukhopadhyay, Synlett, 1997, 876. For other approaches to the formation of dihydrofuran rings, see: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986); H. Hagiwara, K. Kato, T. Suzuki, and M. Ando, Tetrahedron Lett., 38, 2103 (1997).
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    • Lee, Y.R.1    Kim, N.S.2    Kim, B.S.3
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    • 0002527475 scopus 로고    scopus 로고
    • For metal-mediated cycloaddition reactions of 1,3-dicarbonyls to alkenes forming 1,2-dihydrofuran derivatives, see: K. Ichikawa, S. Uemura, and T. Sugita, Tetrahedron, 22, 407 (1966); E. I. Heiba and R. M. Dessau, J. Org. Chem., 39, 3456 (1974); M. G. Vinogradov, A. E. Kondorsky, and G. I. Nikishin, Synthesis, 1988, 60; E. Baciocchi and R. Ruzziconi, Synth. Commun., 18, 1841 (1988), and references cited therein. For recent reports, see: J. M. Mellor and S. Mohammed, Tetrahedron Lett., 32, 7111 (1991); V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1995, 187; 1995, 1881; 1996, 1487; Y. R. Lee and B. S. Kim, Tetrahedron Lett., 38, 2095 (1997); Y. R. Lee, N. S. Kim, and B. S. Kim, Tetrahedron Lett., 38, 5671 (1997). See also: J. Iqbal and M. Mukhopadhyay, Synlett, 1997, 876. For other approaches to the formation of dihydrofuran rings, see: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986); H. Hagiwara, K. Kato, T. Suzuki, and M. Ando, Tetrahedron Lett., 38, 2103 (1997).
    • Synlett , vol.1997 , pp. 876
    • Iqbal, J.1    Mukhopadhyay, M.2
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    • 0000560583 scopus 로고
    • For metal-mediated cycloaddition reactions of 1,3-dicarbonyls to alkenes forming 1,2-dihydrofuran derivatives, see: K. Ichikawa, S. Uemura, and T. Sugita, Tetrahedron, 22, 407 (1966); E. I. Heiba and R. M. Dessau, J. Org. Chem., 39, 3456 (1974); M. G. Vinogradov, A. E. Kondorsky, and G. I. Nikishin, Synthesis, 1988, 60; E. Baciocchi and R. Ruzziconi, Synth. Commun., 18, 1841 (1988), and references cited therein. For recent reports, see: J. M. Mellor and S. Mohammed, Tetrahedron Lett., 32, 7111 (1991); V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1995, 187; 1995, 1881; 1996, 1487; Y. R. Lee and B. S. Kim, Tetrahedron Lett., 38, 2095 (1997); Y. R. Lee, N. S. Kim, and B. S. Kim, Tetrahedron Lett., 38, 5671 (1997). See also: J. Iqbal and M. Mukhopadhyay, Synlett, 1997, 876. For other approaches to the formation of dihydrofuran rings, see: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986); H. Hagiwara, K. Kato, T. Suzuki, and M. Ando, Tetrahedron Lett., 38, 2103 (1997).
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    • Yoshida, J.1    Sakaguchi, K.2    Isoe, S.3
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    • 0031585034 scopus 로고    scopus 로고
    • For metal-mediated cycloaddition reactions of 1,3-dicarbonyls to alkenes forming 1,2-dihydrofuran derivatives, see: K. Ichikawa, S. Uemura, and T. Sugita, Tetrahedron, 22, 407 (1966); E. I. Heiba and R. M. Dessau, J. Org. Chem., 39, 3456 (1974); M. G. Vinogradov, A. E. Kondorsky, and G. I. Nikishin, Synthesis, 1988, 60; E. Baciocchi and R. Ruzziconi, Synth. Commun., 18, 1841 (1988), and references cited therein. For recent reports, see: J. M. Mellor and S. Mohammed, Tetrahedron Lett., 32, 7111 (1991); V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1995, 187; 1995, 1881; 1996, 1487; Y. R. Lee and B. S. Kim, Tetrahedron Lett., 38, 2095 (1997); Y. R. Lee, N. S. Kim, and B. S. Kim, Tetrahedron Lett., 38, 5671 (1997). See also: J. Iqbal and M. Mukhopadhyay, Synlett, 1997, 876. For other approaches to the formation of dihydrofuran rings, see: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986); H. Hagiwara, K. Kato, T. Suzuki, and M. Ando, Tetrahedron Lett., 38, 2103 (1997).
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    • Tetrahedron Lett. , vol.1972 , pp. 4729
    • Frost, D.A.1    Morrison, G.A.2


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