Synthesis of 8-hydroxyquinolines by the cyclization of m-hydroxyphenethyl ketone O-2,4-dinitrophenyloximes

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 445-446

  Uchiyama, Katsuya ^a   Hayashi, Yujiro ^a   Narasaka, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000291457     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6146     Document Type: Article

References (13)

1. Michael, J. P., Nat. Prod. Rep., 1995, 465, and the references cited therein.
2. Silva, E. D.; Miao, S.; Andersen, R. J.; Schultz, L. W.; Clardy, J., Tetrahedron Lett., 1992, 33, 2917.
3. Takemura, Y.; Uchida, H.; Ju-ichi, M.; Omura, M.; Ito, C.; Nakagawa, K.; Ono, T.; Furukawa, H., Heterocycles, 1992, 34, 2123.
4. Kusama, H.; Yamashita, Y.; Narasaka, K., Chem. Lett., 1995, 5.
5. Kusama, H.; Uchiyama, K.; Yamashita, Y.; Narasaka, K., Chem. Lett., 1995, 715.
6. a) There are several examples in which nucleophiles substitute formally with the hydroxy group on the nitrogen atom of oximes, see; Erdik, E; AY, Mehmet., Chem. Rev., 1989, 89, 1947.
7. b) Griot, T.; Wagner-Jauregg, T., Helv. Chim. Acta, 1958, 41, 867;
8. Griot, T.; Wagner-Jauregg, T., Helv. Chim. Acta, 1959, 42, 121.
9. c) Schinzer, D.; Bo, Y., Angew. Chem., Int. Ed. Engl., 1991, 30, 687.
10. Miller, M. J.; Loudon, G. M., J. Org. Chem., 1975, 40, 126.
11. 2, NaH, KH, and LiH, NaH gave the best results.
12. In the case of the methylsulfonyl oxime of 4-(3-hydroxyphenyl)-butan-2-one, the 6- and 8-hydroxy quinolines were obtained in 20% and 7% yield, respectively.
13. When an equimolar amount of DDQ was used, the yield of the quinoline 2a decreased to 49%.