Regioselective synthesis of 8-hydroxytetrahydroquinolines by the cyclization of m-hydroxyphenethyl ketone O-2,4-dinitrophenyloximes

Chemistry Letters

Volumn , Issue 5, 1998, Pages 437-438

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

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032389290     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.437     Document Type: Article

References (16)

1. Review, A. R. Katritzky, S. Rachwal, and B. Rackwal, Tetrahedron, 52, 15031 (1996).
2. M. Cherest and X. Lusinchi, Tetrahedron Lett., 30, 715 (1989).
3. F. Minisci and R. Galli, Tetrahedron Lett., 1966, 2531. Review of aminyl radical, S. Z. Zard, Synlett, 1996, 1148.
4. F. Minisci and R. Galli, Tetrahedron Lett., 1966, 2531. Review of aminyl radical, S. Z. Zard, Synlett, 1996, 1148.
5. a) K Uchiyama, Y. Hayashi, and K. Narasaka, Synlett, 1997, 445.
6. b) H. Kusama, Y. Yamashita, and K. Narasaka, Chem Lett., 1995, 5.
7. c) H. Kusama, K. Uchiyama, Y. Yamashita, and K. Narasaka, Chem Lett., 1995, 715.
8. d) H. Kusama, Y. Yamashita, K. Uchiyama, and K. Narasaka, Bull. Chem. Soc. Jpn., 70, 965 (1997).
9. e) S. Mori, K. Uchiyama, Y. Hayashi, K. Narasaka, and E. Nakamura, Chem. Lett., 1998, 111.
10. 2,4-Dinitrophenyloxime 1a was prepared by the reported procedure. M. J. Miller and G. M. Loudon, J. Org. Chem., 40, 126 (1975). The E-isomer, separated by HPLC from the Z-isomer, was employed in the experiments.
11. Sodium borohydride, zinc borohydride, sodium triacetoxyborohydride, and lithium tri-tert-butoxyaluminum hydride were examined as reducing reagents. In each reaction, the tetrahydroquinoline 4a was obtained in less than 30% yield.
12. 4 protons of the major isomer after conversion of 4d to the corresponding r-butyldimethylsilyl ether4d′. formula presented
13. The oximes 5 and 7 were prepared from the corresponding cis-and trans-(m-hydroxyphenyl)cyclohexyl methyl ketones which were prepared as follows. formula presented
14. 10a 6.5%) after conversion of 6 to the corresponding t-butyldimetnylsilyl ether.
15. 6a (JH6-H6a=9.6 Hz) suggested the stereochemistry as shown in 8.
16. 4 3.2%) after conversion of 11 to the corresponding t-butyldimethylsilyl ether.