Ceric ammonium nitrate mediated cycloaddition of hydroxyquinones with alkenes for the one-step construction of furoquinone derivatives

Chemistry Letters

Volumn , Issue 6, 1996, Pages 451-452

  Kobayashi, Kazuhiro ^a   Mori, Masako ^a   Uneda, Tomokazu ^a   Morikawa, Osamu ^a   Konishi, Hisatoshi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030500338     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.451     Document Type: Article

References (16)

1. R. H. Thomson. "Naturally Occurring Quinones III, Recent Advances," Chapman and Hall, London-New York (1987), pp. 609-633.
2. K. Shishido, T. Takata, T. Omodani, and M. Shibuya, Chem. Lett., 1993, 557; J. M. Heerding and H. W. Moore, J. Org. Chem., 56, 4048 (1991), and references cited in Refs. 3 and 4.
3. K. Shishido, T. Takata, T. Omodani, and M. Shibuya, Chem. Lett., 1993, 557; J. M. Heerding and H. W. Moore, J. Org. Chem., 56, 4048 (1991), and references cited in Refs. 3 and 4.
4. K. Kobayashi, H. Shimizu, A. Sasaki, and H. Suginome, J. Org. Chem., 56, 3204 (1991); 58, 4614 (1993).
5. K. Kobayashi, H. Shimizu, A. Sasaki, and H. Suginome, J. Org. Chem., 56, 3204 (1991); 58, 4614 (1993).
6. K. Kobayashi, Y. Kanno, and H. Suginome, J. Chem. Sec., Perkin Trans. 1, 1993, 1449.
7. Several metal compounds have been used for the production of 1,2-dihydrofuran derivatives by the cycloaddition of 1,3-dicarbonyls to alkenes. For leading references 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); E. Baciocchi and R Ruzziconi, Synth. Commun., 18, 1841 (1988) and references cited therein. In particular, high efficiency of this cerium compound has been recently reported: V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1993, 187. An electrochemical procedure has also been successfully employed: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986).
8. Several metal compounds have been used for the production of 1,2-dihydrofuran derivatives by the cycloaddition of 1,3-dicarbonyls to alkenes. For leading references 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); E. Baciocchi and R Ruzziconi, Synth. Commun., 18, 1841 (1988) and references cited therein. In particular, high efficiency of this cerium compound has been recently reported: V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1993, 187. An electrochemical procedure has also been successfully employed: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986).
9. Several metal compounds have been used for the production of 1,2-dihydrofuran derivatives by the cycloaddition of 1,3-dicarbonyls to alkenes. For leading references 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); E. Baciocchi and R Ruzziconi, Synth. Commun., 18, 1841 (1988) and references cited therein. In particular, high efficiency of this cerium compound has been recently reported: V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1993, 187. An electrochemical procedure has also been successfully employed: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986).
10. Several metal compounds have been used for the production of 1,2-dihydrofuran derivatives by the cycloaddition of 1,3-dicarbonyls to alkenes. For leading references 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); E. Baciocchi and R Ruzziconi, Synth. Commun., 18, 1841 (1988) and references cited therein. In particular, high efficiency of this cerium compound has been recently reported: V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1993, 187. An electrochemical procedure has also been successfully employed: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986).
11. Several metal compounds have been used for the production of 1,2-dihydrofuran derivatives by the cycloaddition of 1,3-dicarbonyls to alkenes. For leading references 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); E. Baciocchi and R Ruzziconi, Synth. Commun., 18, 1841 (1988) and references cited therein. In particular, high efficiency of this cerium compound has been recently reported: V. Nair and J. Matthew, J. Chem. Soc., Perkin Trans. 1, 1993, 187. An electrochemical procedure has also been successfully employed: J. Yoshida, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 27, 6075 (1986).
12. 3: C, 74.98; H, 6.29%. cf. K. Kobayashi, A. Sasaki, H. Takeuchi, and H. Suginome, J. Chem. Soc., Perkin Trans. 1, 1993, 115.
13. L. F. Fieser and A. I. Ardao, J. Am. Chem. Soc., 78, 774 (1956).
14. K. C. Kurien and P. A. Robins, J. Chem. Soc., B, 1970, 855.
15. A. C. Baillie and R. H. Thomson, J. Chem. Soc., C, 1966, 2184.
16. 1H NMR, and MS) together with elemental analyses.