A Convenient Synthesis of 2-Alkylated 1,4-Benzenediols

Synlett

Volumn 1997, Issue 4, 1997, Pages 365-366

  Ozaki, Yutaka ^a   Hosoya, Ayako ^a   Okamura, Kyouko ^a   Kim, Sang Won ^a  

^a JOSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343912604     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-806     Document Type: Article

References (23)

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2. see for example: Cimino, G.; De Stefano, S.; Minale, L. Tetrahedron 1972, 28, 1315. Howard, B. M.; Clarkson, K.; Tetrahedron Lett. 1979, 4449. Ochi, M.; Kotsuki, H.; Inoue, S.; Taniguchi, M.; Tokoroyama, T. Chem. Lett. 1979, 831. Reynolds, G.; Rodriguez, E. Phytochemistry 1979, 18, 1567. Stonik, V. A.; Makarieva, T. N.; Dmitrenok, A. S. J. Nat. Prod. 1992, 55, 1256. De Rosa, S.; Crispino, A.; De Giulio, A.; Iodice, C.; Milone, A. J. Nat. Prod. 1995, 58, 1450. Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 1045.
3. see for example: Cimino, G.; De Stefano, S.; Minale, L. Tetrahedron 1972, 28, 1315. Howard, B. M.; Clarkson, K.; Tetrahedron Lett. 1979, 4449. Ochi, M.; Kotsuki, H.; Inoue, S.; Taniguchi, M.; Tokoroyama, T. Chem. Lett. 1979, 831. Reynolds, G.; Rodriguez, E. Phytochemistry 1979, 18, 1567. Stonik, V. A.; Makarieva, T. N.; Dmitrenok, A. S. J. Nat. Prod. 1992, 55, 1256. De Rosa, S.; Crispino, A.; De Giulio, A.; Iodice, C.; Milone, A. J. Nat. Prod. 1995, 58, 1450. Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 1045.
4. see for example: Cimino, G.; De Stefano, S.; Minale, L. Tetrahedron 1972, 28, 1315. Howard, B. M.; Clarkson, K.; Tetrahedron Lett. 1979, 4449. Ochi, M.; Kotsuki, H.; Inoue, S.; Taniguchi, M.; Tokoroyama, T. Chem. Lett. 1979, 831. Reynolds, G.; Rodriguez, E. Phytochemistry 1979, 18, 1567. Stonik, V. A.; Makarieva, T. N.; Dmitrenok, A. S. J. Nat. Prod. 1992, 55, 1256. De Rosa, S.; Crispino, A.; De Giulio, A.; Iodice, C.; Milone, A. J. Nat. Prod. 1995, 58, 1450. Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 1045.
5. see for example: Cimino, G.; De Stefano, S.; Minale, L. Tetrahedron 1972, 28, 1315. Howard, B. M.; Clarkson, K.; Tetrahedron Lett. 1979, 4449. Ochi, M.; Kotsuki, H.; Inoue, S.; Taniguchi, M.; Tokoroyama, T. Chem. Lett. 1979, 831. Reynolds, G.; Rodriguez, E. Phytochemistry 1979, 18, 1567. Stonik, V. A.; Makarieva, T. N.; Dmitrenok, A. S. J. Nat. Prod. 1992, 55, 1256. De Rosa, S.; Crispino, A.; De Giulio, A.; Iodice, C.; Milone, A. J. Nat. Prod. 1995, 58, 1450. Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 1045.
6. see for example: Cimino, G.; De Stefano, S.; Minale, L. Tetrahedron 1972, 28, 1315. Howard, B. M.; Clarkson, K.; Tetrahedron Lett. 1979, 4449. Ochi, M.; Kotsuki, H.; Inoue, S.; Taniguchi, M.; Tokoroyama, T. Chem. Lett. 1979, 831. Reynolds, G.; Rodriguez, E. Phytochemistry 1979, 18, 1567. Stonik, V. A.; Makarieva, T. N.; Dmitrenok, A. S. J. Nat. Prod. 1992, 55, 1256. De Rosa, S.; Crispino, A.; De Giulio, A.; Iodice, C.; Milone, A. J. Nat. Prod. 1995, 58, 1450. Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 1045.
7. see for example: Cimino, G.; De Stefano, S.; Minale, L. Tetrahedron 1972, 28, 1315. Howard, B. M.; Clarkson, K.; Tetrahedron Lett. 1979, 4449. Ochi, M.; Kotsuki, H.; Inoue, S.; Taniguchi, M.; Tokoroyama, T. Chem. Lett. 1979, 831. Reynolds, G.; Rodriguez, E. Phytochemistry 1979, 18, 1567. Stonik, V. A.; Makarieva, T. N.; Dmitrenok, A. S. J. Nat. Prod. 1992, 55, 1256. De Rosa, S.; Crispino, A.; De Giulio, A.; Iodice, C.; Milone, A. J. Nat. Prod. 1995, 58, 1450. Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 1045.
8. see for example: Asanuma, N.; Ooki, N.; Hirano, S. Jpn. Kokai Tokkyo Koho JP 06298688, 1994; Chem. Abstr. 1995, 123, 1984l4n. Many other patent aplications have been offered.
9. see for example: Asanuma, N.; Ooki, N.; Hirano, S. Jpn. Kokai Tokkyo Koho JP 06298688, 1994; Chem. Abstr. 1995, 123, 1984l4n. Many other patent aplications have been offered.
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11. see for example: Sasaki, M.; Kato, K. Jpn. Kokai Tokkyo Koho JP 05313276, 1993; Chem. Abstr. 1995, 121, 191105n. Hioki, T. Jpn. Kokai Tokkyo Koho JP 05313285, 1993; Chem. Abstr. 1995, 121, 191106p. Ooki, N.; Takahashi, O. Jpn. Kokai Tokkvo Koho JP 06161060, 1994; Chem. Abstr. 1995, 121, 267682w.
12. see for example: Sasaki, M.; Kato, K. Jpn. Kokai Tokkyo Koho JP 05313276, 1993; Chem. Abstr. 1995, 121, 191105n. Hioki, T. Jpn. Kokai Tokkyo Koho JP 05313285, 1993; Chem. Abstr. 1995, 121, 191106p. Ooki, N.; Takahashi, O. Jpn. Kokai Tokkvo Koho JP 06161060, 1994; Chem. Abstr. 1995, 121, 267682w.
13. see for example: Sasaki, M.; Kato, K. Jpn. Kokai Tokkyo Koho JP 05313276, 1993; Chem. Abstr. 1995, 121, 191105n. Hioki, T. Jpn. Kokai Tokkyo Koho JP 05313285, 1993; Chem. Abstr. 1995, 121, 191106p. Ooki, N.; Takahashi, O. Jpn. Kokai Tokkvo Koho JP 06161060, 1994; Chem. Abstr. 1995, 121, 267682w.
14. see for example: Sasaki, M.; Kato, K. Jpn. Kokai Tokkyo Koho JP 05313276, 1993; Chem. Abstr. 1995, 121, 191105n. Hioki, T. Jpn. Kokai Tokkyo Koho JP 05313285, 1993; Chem. Abstr. 1995, 121, 191106p. Ooki, N.; Takahashi, O. Jpn. Kokai Tokkvo Koho JP 06161060, 1994; Chem. Abstr. 1995, 121, 267682w.
15. see for example: Sasaki, M.; Kato, K. Jpn. Kokai Tokkyo Koho JP 05313276, 1993; Chem. Abstr. 1995, 121, 191105n. Hioki, T. Jpn. Kokai Tokkyo Koho JP 05313285, 1993; Chem. Abstr. 1995, 121, 191106p. Ooki, N.; Takahashi, O. Jpn. Kokai Tokkvo Koho JP 06161060, 1994; Chem. Abstr. 1995, 121, 267682w.
16. see for example: Sasaki, M.; Kato, K. Jpn. Kokai Tokkyo Koho JP 05313276, 1993; Chem. Abstr. 1995, 121, 191105n. Hioki, T. Jpn. Kokai Tokkyo Koho JP 05313285, 1993; Chem. Abstr. 1995, 121, 191106p. Ooki, N.; Takahashi, O. Jpn. Kokai Tokkvo Koho JP 06161060, 1994; Chem. Abstr. 1995, 121, 267682w.
17. Brugging, W.; Kampschulte, U.; Schmidt, H.; Heitz, W. Makromol. Chem. 1988, 189, 2755.
18. Butz, L. W.; Rytina, A. W. In Organic Reactions, Vol. 5; Adams, R., Ed.; Wiley: New York, 1949; p 136.
19. Ozaki, Y.; Imaizumi, K.; Okamura, K.; Morozumi, M.; Hosoya, A.; Kim, S. Chem. Pharm. Bull. 1996, 44, 1785 and references cited therein.
20. Mukhopadhyay, T.; Seebach, D. Helv. Chim. Acta 1982, 65, 385.
21. Price, C. C. In Organic Reactions, Vol. 3; Adams, R., Ed.; Wiley: New York, 1946, p 1. Olah, G. A.; Krishnamurti, R.; Prakash, G. K. S. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Ed., Pergamon: Oxford, 1991, p 293.
22. Price, C. C. In Organic Reactions, Vol. 3; Adams, R., Ed.; Wiley: New York, 1946, p 1. Olah, G. A.; Krishnamurti, R.; Prakash, G. K. S. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Ed., Pergamon: Oxford, 1991, p 293.
23. +-complexed enols converted from ketones. Kellehter, R. G.; McKervey, M. A.; Vibuljan, P. J. Chem. Soc., Chem. Commun. 1980, 486. The similar contribution of metal halides was expected in the reactions of 1,4-cyclohexanedione with aldehydes described above.