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Volumn 67, Issue 20, 2002, Pages 7048-7056

Synthesis of β- and γ-carbolines by the palladium/copper-catalyzed coupling and cyclization of terminal acetylenes

Author keywords

[No Author keywords available]

Indexed keywords

THERMAL PROCESSES;

EID: 0037019960     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0258857     Document Type: Article
Times cited : (120)

References (71)
  • 2
    • 0001075641 scopus 로고    scopus 로고
    • Palladium-catalyzed annulation
    • Tsuji, J., Ed.; Elsevier Press: Lausanne, Switzerland
    • (b) Larock, R. C. Palladium-Catalyzed Annulation. In Perspectives in Organopalladium Chemistry for the XXI Century; Tsuji, J., Ed.; Elsevier Press: Lausanne, Switzerland, 1999; pp 111-124.
    • (1999) Perspectives in Organopalladium Chemistry for the XXI Century , pp. 111-124
    • Larock, R.C.1
  • 45
    • 0001247951 scopus 로고
    • Brossi, A., Ed.; Academic Press: San Diego CA
    • (f) Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, CA, 1989; Vol. 36, pp 135-170.
    • (1989) The Alkaloids , vol.36 , pp. 135-170
    • Ohmoto, T.1    Koike, K.2
  • 48
    • 26444617730 scopus 로고
    • Brossi, A., Ed.; Academic Press: San Diego CA, Chapter 7
    • (i) Gribble, G. W. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, CA, 1990; Vol. 39, Chapter 7.
    • (1990) The Alkaloids , vol.39
    • Gribble, G.W.1
  • 56
    • 0002769275 scopus 로고    scopus 로고
    • Diederich, F., Stang, P.J., Eds.; Perspectives in Organopalladium Chemistry for the XXI Century; Wiley-VCH: Weinheim, Germany, Chapter 5
    • Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Perspectives in Organopalladium Chemistry for the XXI Century; Wiley-VCH: Weinheim, Germany, 1998: Chapter 5, pp 203-229.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 203-229
    • Sonogashira, K.1
  • 59
    • 0010596286 scopus 로고    scopus 로고
    • Ethyl propiolate and ethoxyacetylene are prone to polymerization. For examples, see: (a) Gal, Y.-S.; Lee, W.-C.; Choi, S.-K. Korea Polym. J. 1997, 5, 10. (b) Tabata, M.; Inaba, Y.; Yokota, K.; Nozaki, Y. J. Macromol. Sci., Pure Appl. Chem. 1994, 31, 465. (c) Jacobs, T. L.; Juster, N. J. Chem. Eng. Data 1969, 14, 125.
    • (1997) Korea Polym. J. , vol.5 , pp. 10
    • Gal, Y.-S.1    Lee, W.-C.2    Choi, S.-K.3
  • 60
    • 0028259290 scopus 로고
    • Ethyl propiolate and ethoxyacetylene are prone to polymerization. For examples, see: (a) Gal, Y.-S.; Lee, W.-C.; Choi, S.-K. Korea Polym. J. 1997, 5, 10. (b) Tabata, M.; Inaba, Y.; Yokota, K.; Nozaki, Y. J. Macromol. Sci., Pure Appl. Chem. 1994, 31, 465. (c) Jacobs, T. L.; Juster, N. J. Chem. Eng. Data 1969, 14, 125.
    • (1994) J. Macromol. Sci., Pure Appl. Chem. , vol.31 , pp. 465
    • Tabata, M.1    Inaba, Y.2    Yokota, K.3    Nozaki, Y.4
  • 61
    • 2142648741 scopus 로고
    • Ethyl propiolate and ethoxyacetylene are prone to polymerization. For examples, see: (a) Gal, Y.-S.; Lee, W.-C.; Choi, S.-K. Korea Polym. J. 1997, 5, 10. (b) Tabata, M.; Inaba, Y.; Yokota, K.; Nozaki, Y. J. Macromol. Sci., Pure Appl. Chem. 1994, 31, 465. (c) Jacobs, T. L.; Juster, N. J. Chem. Eng. Data 1969, 14, 125.
    • (1969) J. Chem. Eng. Data. , vol.14 , pp. 125
    • Jacobs, T.L.1    Juster, N.2
  • 62
    • 37049175530 scopus 로고
    • The base-promoted deacetonation of α,β-acetylenic carbinols has been well-studied. For representative examples, see: (a) Veliev, M. G.; Shatirova, M. I.; Chalabiev, C. A.; Mamedov, I. M.; Mustafaev, A. M. Russ. J. Org. Chem. 1995, 31, 52. (b) Havens, S. J.; Hergenrother, P. M. J. Org. Chem. 1985, 50, 1763. (c) Fowler, J. S. J. Org. Chem. 1977, 42, 2637. The base-promoted fragmentation of a 1-hydroxycy-clohexyl-substituted acetylene is also known. See: (d) Henbest, H. B.; Jones, E. R. H.; Walls, I. M. S. J. Chem. Soc. 1949, 2696.
    • (1995) Russ. J. Org. Chem. , vol.31 , pp. 52
    • Veliev, M.G.1    Shatirova, M.I.2    Chalabiev, C.A.3    Mamedov, I.M.4    Mustafaev, A.M.5
  • 63
    • 0000692771 scopus 로고
    • The base-promoted deacetonation of α,β-acetylenic carbinols has been well-studied. For representative examples, see: (a) Veliev, M. G.; Shatirova, M. I.; Chalabiev, C. A.; Mamedov, I. M.; Mustafaev, A. M. Russ. J. Org. Chem. 1995, 31, 52. (b) Havens, S. J.; Hergenrother, P. M. J. Org. Chem. 1985, 50, 1763. (c) Fowler, J. S. J. Org. Chem. 1977, 42, 2637. The base-promoted fragmentation of a 1-hydroxycy-clohexyl-substituted acetylene is also known. See: (d) Henbest, H. B.; Jones, E. R. H.; Walls, I. M. S. J. Chem. Soc. 1949, 2696.
    • (1985) J. Org. Chem. , vol.50 , pp. 1763
    • Havens, S.J.1    Hergenrother, P.M.2
  • 64
    • 0017781176 scopus 로고
    • The base-promoted deacetonation of α,β-acetylenic carbinols has been well-studied. For representative examples, see: (a) Veliev, M. G.; Shatirova, M. I.; Chalabiev, C. A.; Mamedov, I. M.; Mustafaev, A. M. Russ. J. Org. Chem. 1995, 31, 52. (b) Havens, S. J.; Hergenrother, P. M. J. Org. Chem. 1985, 50, 1763. (c) Fowler, J. S. J. Org. Chem. 1977, 42, 2637. The base-promoted fragmentation of a 1-hydroxycy-clohexyl-substituted acetylene is also known. See: (d) Henbest, H. B.; Jones, E. R. H.; Walls, I. M. S. J. Chem. Soc. 1949, 2696.
    • (1977) J. Org. Chem. , vol.42 , pp. 2637
    • Fowler, J.S.1
  • 65
    • 37049175530 scopus 로고
    • The base-promoted deacetonation of α,β-acetylenic carbinols has been well-studied. For representative examples, see: (a) Veliev, M. G.; Shatirova, M. I.; Chalabiev, C. A.; Mamedov, I. M.; Mustafaev, A. M. Russ. J. Org. Chem. 1995, 31, 52. (b) Havens, S. J.; Hergenrother, P. M. J. Org. Chem. 1985, 50, 1763. (c) Fowler, J. S. J. Org. Chem. 1977, 42, 2637. The base-promoted fragmentation of a 1-hydroxycy-clohexyl-substituted acetylene is also known. See: (d) Henbest, H. B.; Jones, E. R. H.; Walls, I. M. S. J. Chem. Soc. 1949, 2696.
    • (1949) J. Chem. Soc. , pp. 2696
    • Henbest, H.B.1    Jones, E.R.H.2    Walls, I.M.S.3
  • 68
    • 2142820889 scopus 로고    scopus 로고
    • note
    • 3 also afforded the corresponding desilylated β-carboline in a low yield (37%). See ref 5a for details.
  • 70
    • 0031585045 scopus 로고    scopus 로고
    • Gilchrist, T. L.; Kemmitt, P. D.; Germain, A. L. Tetrahedron 1997, 53, 4447. We used ethyl acetate instead of diethyl ether as the extraction solvent, and were able to isolate 2-bromo-1H-indole-3-carboxaldehyde in a 55% yield.
    • (1997) Tetrahedron , vol.53 , pp. 4447
    • Gilchrist, T.L.1    Kemmitt, P.D.2    Germain, A.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.