Highly Regioselective Anodic Monofluorination of Oxindole and 3-Oxo-1,2,3,4-tetrahydroisoquinoline Derivatives

Synlett

Volumn 1997, Issue 6, 1997, Pages 655-656

  Hou, Yankun ^a   Higashiya, Seiichiro ^a   Fuchigami, Toshio ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003087848     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3272     Document Type: Article

References (13)

1. Electrochemical Partical Fluorination of Organic Compounds.Part 21. Part 20. Fujita, T.; Fuchigami, T. Tetrahedron Lett. 1996, 37, 4752.
2. Biomedicinal Aspects of Fluorine Chemictry, Filler, R.; Kobayashi, Y. Eds.; Kodansha & Elsevier Biomedical, Tokyo, 1982.
3. For Example, see: Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J.T.Ed; ACS Books: Washington D.C., 1991.
4. Erian, A.W.; Konno, A.; Fuchigami, T. J. Org. Chem. 1995, 60, 7654: References are cited therein.
5. Gambaretto, G.P.; Napoli, M.; Conte, L. J. Fluorine Chem. 1982, 19, 427. Ballinger, J. R.; Teare, F. W. Electrochim. Acta., 1985, 30. 1075. Makino, K.; Yoshioka, H. J. Fluorine Chem. 1988, 39, 435. Meurs, J. H.H.; Eilenberg, W. Tetrahedron, 1991, 47, 705. Sono, M.; Morita, N.; Shizuri, Y.; Tori, M. Tetrahedron Lett. 1994, 35, 9237.
6. Gambaretto, G.P.; Napoli, M.; Conte, L. J. Fluorine Chem. 1982, 19, 427. Ballinger, J. R.; Teare, F. W. Electrochim. Acta., 1985, 30. 1075. Makino, K.; Yoshioka, H. J. Fluorine Chem. 1988, 39, 435. Meurs, J. H.H.; Eilenberg, W. Tetrahedron, 1991, 47, 705. Sono, M.; Morita, N.; Shizuri, Y.; Tori, M. Tetrahedron Lett. 1994, 35, 9237.
7. Gambaretto, G.P.; Napoli, M.; Conte, L. J. Fluorine Chem. 1982, 19, 427. Ballinger, J. R.; Teare, F. W. Electrochim. Acta., 1985, 30. 1075. Makino, K.; Yoshioka, H. J. Fluorine Chem. 1988, 39, 435. Meurs, J. H.H.; Eilenberg, W. Tetrahedron, 1991, 47, 705. Sono, M.; Morita, N.; Shizuri, Y.; Tori, M. Tetrahedron Lett. 1994, 35, 9237.
8. Gambaretto, G.P.; Napoli, M.; Conte, L. J. Fluorine Chem. 1982, 19, 427. Ballinger, J. R.; Teare, F. W. Electrochim. Acta., 1985, 30. 1075. Makino, K.; Yoshioka, H. J. Fluorine Chem. 1988, 39, 435. Meurs, J. H.H.; Eilenberg, W. Tetrahedron, 1991, 47, 705. Sono, M.; Morita, N.; Shizuri, Y.; Tori, M. Tetrahedron Lett. 1994, 35, 9237.
9. Gambaretto, G.P.; Napoli, M.; Conte, L. J. Fluorine Chem. 1982, 19, 427. Ballinger, J. R.; Teare, F. W. Electrochim. Acta., 1985, 30. 1075. Makino, K.; Yoshioka, H. J. Fluorine Chem. 1988, 39, 435. Meurs, J. H.H.; Eilenberg, W. Tetrahedron, 1991, 47, 705. Sono, M.; Morita, N.; Shizuri, Y.; Tori, M. Tetrahedron Lett. 1994, 35, 9237.
10. Momota, K.; Morita, M.; Matsuda, Y. Electrochim. Acta. 1993, 38, 1231.
11. 18NSOF m/z 363.1093, found m/z 363.1091.
12. 4NF•4HF/ MeCN, polyfluorination took place at the benzene ring predominantly, but the heterocyclic moiety was not fluorinated at all: Kato, K.; Momota, K. The 18th Symposium on Electroorganic Chemistry, Nagoya, Jpn, 1995, Abstr. 101.
13. Umemeto, T.; Tomizawa, G. Bull. Chem. Soc. Jpn. 1986, 59, 3625.