Diethoxymethyl protected indoles: Synthesis and regioselective transformations

Synthesis

Volumn , Issue 10, 1996, Pages 1196-1198

  Gmeiner, Peter ^a   Kraxner, Johannes ^a   Bollinger, Bernd ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029808582     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4356     Document Type: Article

References (18)

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2. Curtis, N.J.; Brown, R.S. J. Org. Chem. 1980, 45, 4038. Ohta, S.; Yuasa, T.; Narita, Y.; Kawasaki, I.; Minamii, E.; Yamashita, M. Heterocycles, 1991, 32, 1923.
3. Gmeiner, P.; Bollinger, B. Synthesis 1995, 168.
4. Gmeiner, P.; Bollinger, B. Tetrahedron Lett. 1991, 32, 5927. Gmeiner, P.; Bollinger, B.; Mierau, J.; Höfner, G. Arch. Pharm. (Weinheim) 1995, 328, 609.
5. Gmeiner, P.; Bollinger, B. Tetrahedron Lett. 1991, 32, 5927. Gmeiner, P.; Bollinger, B.; Mierau, J.; Höfner, G. Arch. Pharm. (Weinheim) 1995, 328, 609.
6. For previous examples on the N-protection of indoles, see: Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991; p 385.
7. Three entities for indole-1-carbaldehyde diethyl acetal derivatives are noted in the literature. As a tryptamine derived intermediate for the synthesis of rutaecarpine, see: Bergman, J.; Bergman, S. J. Org. Chem. 1985, 50, 1246. As a carbazole derivative, see: Witzel, H.; Pindur, U. J. Heterocyclic Chem. 1988, 25, 907. As derivatives of 5-methoxy-2,3-diphenylindole, see: El-Diwani, H. I.; Shmeiss, N. A. M. M.; Saleigh, N. M. Pol. J. Chem. 1995, 69, 470.
8. Three entities for indole-1-carbaldehyde diethyl acetal derivatives are noted in the literature. As a tryptamine derived intermediate for the synthesis of rutaecarpine, see: Bergman, J.; Bergman, S. J. Org. Chem. 1985, 50, 1246. As a carbazole derivative, see: Witzel, H.; Pindur, U. J. Heterocyclic Chem. 1988, 25, 907. As derivatives of 5-methoxy-2,3-diphenylindole, see: El-Diwani, H. I.; Shmeiss, N. A. M. M.; Saleigh, N. M. Pol. J. Chem. 1995, 69, 470.
9. Three entities for indole-1-carbaldehyde diethyl acetal derivatives are noted in the literature. As a tryptamine derived intermediate for the synthesis of rutaecarpine, see: Bergman, J.; Bergman, S. J. Org. Chem. 1985, 50, 1246. As a carbazole derivative, see: Witzel, H.; Pindur, U. J. Heterocyclic Chem. 1988, 25, 907. As derivatives of 5-methoxy-2,3-diphenylindole, see: El-Diwani, H. I.; Shmeiss, N. A. M. M.; Saleigh, N. M. Pol. J. Chem. 1995, 69, 470.
10. Pindur, U. In The Chemisty of Acid Derivatives, Vol. 2, Supplement B; Patai, S., Ed.; Wiley: New York, 1992. Akgün, E.; Pindur, U.; Müller, J. J. Heterocycl. Chem. 1983, 20, 1303.
11. Pindur, U. In The Chemisty of Acid Derivatives, Vol. 2, Supplement B; Patai, S., Ed.; Wiley: New York, 1992. Akgün, E.; Pindur, U.; Müller, J. J. Heterocycl. Chem. 1983, 20, 1303.
12. For previous 2-metalations and reactions of N-protected indoles, see: Sundberg, R. J.; Russell, H. F. J. Org. Chem. 1973, 38, 3324. Gharpure, M.; Stoller, A.; Bellamy, F.; Firnau, G.; Snieckus, V. Synthesis 1991, 1079, and references cited therein.
13. For previous 2-metalations and reactions of N-protected indoles, see: Sundberg, R. J.; Russell, H. F. J. Org. Chem. 1973, 38, 3324. Gharpure, M.; Stoller, A.; Bellamy, F.; Firnau, G.; Snieckus, V. Synthesis 1991, 1079, and references cited therein.
14. For recent examples on palladium-catalyzed coupling reactions of N-protected indol-2-yltributylstannanes, see: Labadie, S. S.; Teng, E. J. Org. Chem. 1994, 59, 4250. Hudkins, R. L.; Diebold, J. L.; Marsh, F. D. J. Org. Chem. 1995, 60, 6218, and references cited therein.
15. For recent examples on palladium-catalyzed coupling reactions of N-protected indol-2-yltributylstannanes, see: Labadie, S. S.; Teng, E. J. Org. Chem. 1994, 59, 4250. Hudkins, R. L.; Diebold, J. L.; Marsh, F. D. J. Org. Chem. 1995, 60, 6218, and references cited therein.
16. Nechvatal, G.; Widdowson, D. A.; Williams, D. J. J. Chem. Soc. Chem. Commun. 1981, 1260. Beswick, P. J.; Greenwood, C. S.; Mowlem, T. J.; Nechvatal, G.; Widdowson, D. A. Tetrahedron 1988, 44, 7325.
17. Nechvatal, G.; Widdowson, D. A.; Williams, D. J. J. Chem. Soc. Chem. Commun. 1981, 1260. Beswick, P. J.; Greenwood, C. S.; Mowlem, T. J.; Nechvatal, G.; Widdowson, D. A. Tetrahedron 1988, 44, 7325.
18. Jaouen, G.; Debard, R. Tetrahedron Lett. 1971, 1015.