Oxidation of 1-Tetralone Oximes with 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in Non-aqueous AcOH-Benzene Media: Easy and Efficient Preparation of Naphthoquinone Monooximes

Synlett

Volumn 1997, Issue 2, 1997, Pages 161-162

  Watanabe, Toshiko ^a   Oku, Yumie ^a   Ishii, Hisashi ^a   Ishikawa, Tsutomu ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0342514736     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-752     Document Type: Article

References (15)

1. a) Simanek, V. In The Alkaloids, Vol: 26; Brossi, A., Ed.; Academic: New York, 1983; p 185;
2. b) Herbert, J. M.; Augereau, J. M.; Gleye, J.; Maffrand, J. P. Biochem. Biophys. Res. Commun. 1990, 172, 993;
3. c) Fang, S. -D.; Wang, L. -K.; Hecht, S. M. J. Org. Chem. 1993, 58, 5025.
4. Ishii, H.; Ishikawa, T.; Takeda, S.; Suzuki, M.; Harayama, T. Chem. Pharm. Bull. 1992, 40, 2002 and references cited therein.
5. Ishikawa, T.; Saito, T.; Ishii, H. Tetrahedron 1995, 51, 8447.
6. Ishikawa, T.; Watanabe, T.; Tanigawa, H.; Saito, T.; Kotake, K. -I.; Ohashi, Y.; Ishii, H. J. Org. Chem. 1996, 61, 2774.
7. 9
8. Rathore, R.; Saxena, N.; Chandrasekaran, S. Synth. Commun. 1986, 16, 1493.
9. 8: C, 60.96; H, 6.28; N, 3.23. Found: C. 60.66; H, 6.29; N, 3.47.
10. Lee, H.; Harvey, R. G. J. Org. Chem. 1988, 53, 4587.
11. +, 38%), 351 (base peak).
12. 7: C, 63.92; H, 5.61; N, 3.39. Found: C, 63.62; H, 5.43; N, 3.33.
13. Harvey et al. observed the double oxidation with DDQ in aqueous dioxane in the case of 1, 10-trimethylenephenanthrene [Lee, H.; Harvey, R. G. J. Org. Chem. 1983, 48, 749].
14. a) Gould, S. J.; Tamayo, N.; Melville, C. R.; Cone, M. C. J. Am. Chem. Soc. 1994, 116, 2207;
15. b) Cone, M. C.; Melville, C. R.; Gore, S. J.; Gould, S. J. J. Org. Chem. 1993, 58, 1058.