Indole synthesis by Pd-catalyzed annulation of ketones with o-iodoaniline: 1,2,3,4-tetrahydrocarbazole: [ 1H-carbazole, 2,3,4,9-tetrahydro- ]

Organic Syntheses

Volumn 78, Issue , 2002, Pages 36-

  Chen, Cheng yi ^b   Larsen, Robert D ^a   Charnley, Adam ^b   Wolff, Steven ^b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34948828777     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.078.0036     Document Type: Article

References (14)

1. Saxton, J. E. "The Chemistry of Heterocyclic Compounds"; John Wiley and Sons: New York, 1994; Vol. 25, Part IV.
2. For reviews on the Fischer indole reaction, see: Robinson, B. "The Fischer Indole Synthesis"; John Wiley and Sons: New York, 1982;
3. Hughes, D. L. Org. Prep. Proced. Int. 1993, 25, 607;
4. Gribble, G. W. Contemp. Org. Synth. 1994, 1, 145 and references cited therein.
5. (a) Beugelmans, R.; Roussi, G. J. Chem. Soc., Chem. Commun. 1979, 950;
6. (b) Bard, R. R.; Bunnett, J. J. J. Org. Chem. 1980, 45, 1546;
7. (c) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127;
8. (d) Suzuki, H.; Thiruvikraman, S. V.; Osuka, A. Synthesis 1984, 616 and references cited therein;
9. (e) dAngelo, J.; Desmaele, D.; Tetrahedron Lett. 1990, 31, 879.
10. Chen, C.-y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676 and references cited therein.
11. Maruoka, K.; Oishi, M.; Yamamoto, H. J. Org. Chem. 1993, 58, 7638.
12. Chen, C.-y; Lieberman, D. R.; Larsen, R. D.; Reamer, R. A.; Verhoeven, T. R.; Reider, P. J.; Cottrell, I. F.; Houghton, P. G. Tetrahedron Lett. 1994, 35, 6981.
13. A Fischer indole reaction in pyridine has been reported: Welch, W. M. Synthesis 1977, 645.
14. Cook, A. G. "Enamines: Synthesis, Structure, and Reactions", 2nd ed.; Marcel Dekker, Inc.: New York, 1988.