Regioselective Fischer Indole Synthesis Mediated by Organoaluminum Amides

Journal of Organic Chemistry

Volumn 58, Issue 27, 1993, Pages 7638-7639

  Maruoka, Keiji ^a   Oishi, Masataka ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0027717937     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00079a005     Document Type: Article

References (20)

1. Fischer, E.; Jourdan, F. Ber. 1883, 16, 2241.
2. Fischer, E.; Hess, O. Ber. 1884, 17, 559.
3. Reviews of Fischer indole synthesis: (a) Robinson, B. Chem. Rev. 1963, 63, 373;
4. 1969, 69, 227.
5. Remers, W. A.; Brown, R. K. In Indole; Houlihan, W. J., Ed.; Wiley-Interscience: New York, 1972; 232–317.
6. Ishii, H. Acc. Chem. Res. 1981, 14, 275.
7. Reviews of indole synthesis: (a) Katritzky, A. R.; Rees, C. W. Comprehensive Heterocyclic Chemistry; Pergamon: Oxford, 1984; Vol. 4.
8. Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113.
9. Manske, R. H. F. The Alkaloids; Wiley: New York, 1950-1979; Vols. 1-17.
10. Hesse, M. Indolalkaloide in Tabellen; Springer: Berlin, 1964.
11. Glasby, J. S. Encyclopedia of the Alkaloids; Plenum Press: New York, 1975.
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13. 1924, 125, 827.
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16. Hughes, D. L.; Zhao, D. J. Org. Chem. 1993, 58, 228.
17. Organoaluminum amides can be easily prepared from the corresponding lithium amides and a dialkylaluminum halide. See: Mole, T.; Jeffrey, E. A. Organoaluminum Compounds; Elsevier: Amsterdam, 1972.
18. Yasuda, A.; Tanaka, S.; Oshima, K.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1974, 96, 6513.
19. 13C NMR analysis. See: Prochazka, M. P.; Carlson, R. Acta Chem. Scand. 1989, 43, 651.
20. Snyder, H. R.; Smith, C. W. J. Am. Chem. Soc. 1943, 65, 2452.