A new approach to 5-hydroxyindoles from 1,4-cyclohexanedione

Chemistry Letters

Volumn , Issue 7, 1997, Pages 679-680

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

^a JOSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031487864     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.679     Document Type: Article

References (21)

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2. See for example: T. Y. Shen, C. A. Winetr, in "Advance in Drug Research," ed by A. B. Simmons, Academic Press, New York (1977), Vol. 12, p. 89; P. M. Vanhoutte, in "Serotonin and the Cardiovascular System," Raven Press, New York (1985), p. 280.
3. See for example: R. T. Brown, J. A. Joule, and P. G. Sammes, in "Comprehensive Organic Chemistry," ed by P. G. Sammes, Pergamon Press, Oxford (1979), Vol. 4, p.411; U. Pindur and R. Adam, J. Heterocyclic Chem., 25, 1 (1988); J. Bosch and M. Bennasar, Synlett, 1995, 587; E. D. Cox and J. M. Cook, Chem. Rev., 95, 1797 (1995).
4. See for example: R. T. Brown, J. A. Joule, and P. G. Sammes, in "Comprehensive Organic Chemistry," ed by P. G. Sammes, Pergamon Press, Oxford (1979), Vol. 4, p.411; U. Pindur and R. Adam, J. Heterocyclic Chem., 25, 1 (1988); J. Bosch and M. Bennasar, Synlett, 1995, 587; E. D. Cox and J. M. Cook, Chem. Rev., 95, 1797 (1995).
5. See for example: R. T. Brown, J. A. Joule, and P. G. Sammes, in "Comprehensive Organic Chemistry," ed by P. G. Sammes, Pergamon Press, Oxford (1979), Vol. 4, p.411; U. Pindur and R. Adam, J. Heterocyclic Chem., 25, 1 (1988); J. Bosch and M. Bennasar, Synlett, 1995, 587; E. D. Cox and J. M. Cook, Chem. Rev., 95, 1797 (1995).
6. See for example: R. T. Brown, J. A. Joule, and P. G. Sammes, in "Comprehensive Organic Chemistry," ed by P. G. Sammes, Pergamon Press, Oxford (1979), Vol. 4, p.411; U. Pindur and R. Adam, J. Heterocyclic Chem., 25, 1 (1988); J. Bosch and M. Bennasar, Synlett, 1995, 587; E. D. Cox and J. M. Cook, Chem. Rev., 95, 1797 (1995).
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8. See for example: G. R. Allen, Jr., in "Organic Reactions," ed by W. G. Dauben, John Wiley & Sons, New York (1973), Vol. 20, Chap. 3, p. 337; J. M. Pawlak, V. V. Khau, D. R. Hutchison, and M. J. Martinelli, J. Org. Chem., 61, 9055 (1996); R. M. Coates, P. A. MacManus, J. Org. Chem., 24, 4822 (1982); J. F. Poleto, G. R. Allen, Jr., A. E. Sloboda, and M. J. Weiss, J. Med. Chem., 16, 757 (1973).
9. See for example: G. R. Allen, Jr., in "Organic Reactions," ed by W. G. Dauben, John Wiley & Sons, New York (1973), Vol. 20, Chap. 3, p. 337; J. M. Pawlak, V. V. Khau, D. R. Hutchison, and M. J. Martinelli, J. Org. Chem., 61, 9055 (1996); R. M. Coates, P. A. MacManus, J. Org. Chem., 24, 4822 (1982); J. F. Poleto, G. R. Allen, Jr., A. E. Sloboda, and M. J. Weiss, J. Med. Chem., 16, 757 (1973).
10. See for example: G. R. Allen, Jr., in "Organic Reactions," ed by W. G. Dauben, John Wiley & Sons, New York (1973), Vol. 20, Chap. 3, p. 337; J. M. Pawlak, V. V. Khau, D. R. Hutchison, and M. J. Martinelli, J. Org. Chem., 61, 9055 (1996); R. M. Coates, P. A. MacManus, J. Org. Chem., 24, 4822 (1982); J. F. Poleto, G. R. Allen, Jr., A. E. Sloboda, and M. J. Weiss, J. Med. Chem., 16, 757 (1973).
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12. See for example: R. D. Clark, J. M. Muchowski, L. E. Fisher, L. A. Flippin, D. B. Repke, and M. Souchet, Synthesis, 1991, 871; E. Shaw, J. Am. Chem. Soc., 77, 4319 (1955).
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14. See for example: J. S. Zweig and N. Castagnoli, Jr., J. Med. Chem., 17, 747 (1974); J. S. Zweig and N. Castagnoli, Jr., J. Med. Chem., 20, 414 (1977); P. Jacob III, T. Kline, and N. Castagnoli, Jr., J. Med. Chem., 22, 662 (1979).
15. See for example: J. S. Zweig and N. Castagnoli, Jr., J. Med. Chem., 17, 747 (1974); J. S. Zweig and N. Castagnoli, Jr., J. Med. Chem., 20, 414 (1977); P. Jacob III, T. Kline, and N. Castagnoli, Jr., J. Med. Chem., 22, 662 (1979).
16. Presented at the 117th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1997; Y. Ozaki, A. Hosoya, K. Okamura, and S. Kim, Synlett., accepted.
17. Presented at the 117th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1997; Y. Ozaki, A. Hosoya, K. Okamura, and S. Kim, Synlett., accepted.
18. J. Fehrentz and B. Castro, Synthesis, 1983, 676.
19. 4. After evaporation of the solvent, the residue was purified by column chromatography to give 1,4-benzenediol derivatives (4).
20. 2-] were optically inactive. These results indicated that racemization occurred during the condensations.
21. 1H-NMR spectra of these indole derivatives indicated the presence of C-3 protons along with other aromatic protons. The former were found in the range of δ 6.1 to δ 6.7.