Synthesis of 4-acetoxyindoles and related derivatives by means of air oxidation of 4-oxo-4,5,6,7-tetrahydroindoles obtained from nitroalkenes and cyclohexane-1,3-diones

Synlett

Volumn , Issue 1, 2009, Pages 122-126

  Arai, Masaki ^a   Miyauchi, Yayoi ^a   Miyahara, Tadashi ^a   Ishikawa, Teruhiko ^a   Saito, Seiki ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Cyclohexane 1,3 diones; Indoles; Michael additions; Nitroalkenes; Oxidations

Indexed keywords

EID: 62349139519     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087386     Document Type: Article

References (23)

1. For recent syntheses for 4-hydroxyindoles, see: (a) Gathergood, N.; Scammells, P. J. Org. Lett. 2003, 5, 921.
2. (b) Shirota, O.; Hakamata, W.; Goda, Y. J. Nat. Prod. 2003, 66, 885; and references cited therein.
3. (c) For the structure-activity relationship study of II, see: Repke, D. B.; Grotjahn, D. B.; Shulgin, A. T. J. Med. Chem. 1985, 28, 892.
4. Liou, J.-P.; Wu, Z.-Y.; Kuo, C.-C.; Chang, C.-Y.; Lu, P.-Y.; Chen, C.-M.; Hsieh, H.-P.; Chang, J.-Y. J. Med. Chem. 2008, 51, 4351.
5. (a) Ishikawa, T.; Kadoya, R.; Arai, M.; Takahashi, H.; Kaisi, Y.; Mizuta, T.; Yoshikai, K.; Saito, S. J. Org. Chem. 2001, 66, 8000.
6. (b) Ishikawa, T.; Miyahara, T.; Asakura, M.; Higuchi, S.; Miyauchi, Y.; Saito, S. Org. Lett. 2005, 7, 1211.
7. For KF-catalyzed synthesis of 2-hydroxyiminodihydrofurans, see: Miyashita, M.; Kumazawa, T.; Yoshikoshi, A. J. Org. Chem. 1980, 45, 2945.
8. Yanami, T.; Ballatore, A.; Miyashita, M.; Kato, M.; Yoshikoshi, A. J. Chem. Soc., Perkin Trans. 1 1978, 1144.
9. For the synthesis of 4-oxo-4,5,6,7-tetrahydroindoles, see: (a) Leonarda, P.; Chiara, G.; Giacomo, M.; Maurizio, T. Tetrahedron Lett. 2008, 49, 459.
10. (b) Kathriarachchi, K. K. A. D. S.; Siriwardana, A. I.; Nakamura, I.; Yamamoto, Y. Tetrahedron Lett. 2007, 48, 2267.
11. (c) Nayyar, N. K.; Hutchison, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982.
12. (d) Matsumoto, M.; Watanabe, N. Heterocycles 1984, 22, 2313.
13. (e) Bobbitt, J. M.; Kulkarni, C. L.; Dutta, C. P.; Kofod, H.; Chiong, K. N. J. Org. Chem. 1978, 43, 3541.
14. 4-Oxo-4,5,6,7-tetrahydroindoles with no substituent at C(3) can be converted into 4-hydroxyindoles by Pd-catalyzed dehydrogenation or DDQ oxidation though in low yields, see: Remers, W. A.; Roth, R. H.; Gibs, G. J.; Weis, M. J. J. Org. Chem. 1971, 36, 1232.
15. For aromatization of six-membered carbocycles by air oxidation, see: (a) Kawashita, Y.; Nakamichi, N.; Kawabata, H.; Hayashi, M. Org. Lett. 2003, 5, 3713.
16. (b) Ishikawa, T.; Hino, K.; Yoneda, T.; Murota, M.; Yamaguchi, K.; Watanabe, T. J. Org. Chem. 1999, 64, 5691.
17. For the synthesis of 4-hydroxyindoles, see: (a) Somei, M.; Yamada, F. Heterocycles 2000, 53, 1573.
18. (b) Matsumoto, M.; Ishoda, Y.; Watanabe, N. Heterocycles 1986, 24, 165.
19. (c) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282.
20. (d) Remers, W. A.; Weiss, M. J. J. Am. Chem. Soc. 1965, 87, 5262.
21. We are considering that transformation of I-A to I-C may involve an intermediary adduct I-B although nucleophilic attack of electron-rich dienamine function in I-A toward oxygen molecule, if any, might directly give I-C from I-A and could not be ruled out.
22. Schreiber, S. L. Science 2000, 287, 1964.
23. For general synthesis of cyclohexane-1,3-diones, see ref. 3a.