Reaction of organolithiums with fluoro-N,N-diallylanilines: A benzyne-mediated anionic cascade leading to 3,4-disubstituted indolines

Tetrahedron Letters

Volumn 38, Issue 8, 1997, Pages 1329-1332

  Bailey, William F ^a   Carson, Matthew W ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0031584941     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00032-4     Document Type: Article

References (15)

1. 1. (a) Bailey, W. F.; Jiang, X.-L. J. Org. Chem. 1996, 61, 2596.
2. (b) Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1996, 61, 2594.
3. 2. (a) Gschwend, H. W.; Rodriguez, H. R. Org. React, 1979, 1.
4. (b) Snieckus, V. Chem. Rev. 1990, 90, 879.
5. (c) Wittig, G.; Pieper, G.; Fuhrmann, G. Chem. Ber. 1940, 73, 1193.
6. (d) Gilman, H.; Soddy, T. S. J. Org. Chem. 1957, 22, 1715.
7. 3. Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967.
8. 13C NMR spectra are fully in accord with the assigned structures.
9. 5. Lemaire-Audoire, S.; Savignac, M.; Genêt, J. P.; Bernard, J.-M. Tetrahedron Lett. 1995, 36, 1267.
10. 2O, there was no deuterium above the natural abundance level on any aromatic carbon of 5. (formula presented)
11. 7. (a) Bauer, W.; Schleyer, P. v. R. J. Am. Chem. Soc. 1989, 111, 7191.
12. (b) Katsoulos, G.; Takagishi, S.; Schlosser, M. Synlett 1991, 731.
13. 8. In this connection, it is should be noted that addition of PhLi to 3-(dimethylamino)-1,2-dehydrobenzene is reported to give 3-(dimethylamino)biphenyl as the major product: Möbius, L. Doctoral Dissertation, Universität München, 1961, as reported in ref. 3, p. 107. For other regioselective additions of organolithiums to 3-substituted benzynes, see: (a) Adejare, A.; Miller, D. D. Tetrahedron Lett. 1984, 25, 5597.
14. (b) Pansegrau, P. D.; Rieker, W. F.; Meyers, A. I. J. Am. Chem. Soc. 1988, 110, 7178.
15. (c) Mulhern, T. A.; Davis, M.; Krikke, J. J.; Thomas, J. A. J. Org. Chem. 1993, 58, 5537.