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Volumn 28, Issue 1, 1996, Pages 1-64

Synthesis of β-carbolines. A review

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Indexed keywords


EID: 0013626011     PISSN: 00304948     EISSN: 19455453     Source Type: Journal    
DOI: 10.1080/00304949609355907     Document Type: Review
Times cited : (105)

References (153)
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    • Husson, H.-P.1
  • 2
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    • Plenum Press: New York, and references therein
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    • (1989) Encyclopedia of the Alkaloids , vol.1 , pp. 659-661
    • Glasby, J.S.1
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    • Canthin-6-one Alkaloids
    • A. Brossi, Ed., Academic Press: San Diego
    • T. Ohmoto and K. Koike, “Canthin-6-one Alkaloids,” in The Alkaloids, Vol. 36, A. Brossi, Ed., Academic Press: San Diego, 1989; pp. 135-170.
    • (1989) The Alkaloids , vol.36 , pp. 135-170
    • Ohmoto, T.1    Koike, K.2
  • 44
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    • references contained therein
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    • (1987) Tetrahedron Lett. , vol.28
    • Bailey, P.D.1
  • 70
    • 43949163632 scopus 로고
    • Other analogs of vincamine were similarly modified. The synthesis, in fact, utilized a Bischler-Napieralski reaction rather than a Pictet-Spengler reaction to form the p-carboline ring, but the initial starting materials for these two reactions are the same
    • G. Lewin, C. Schaeffer, A. Pierre, N. Guilbaud, G. Atassi and J. Poisson, Heterocycles, 36, 2707 (1993). Other analogs of vincamine were similarly modified. The synthesis, in fact, utilized a Bischler-Napieralski reaction rather than a Pictet-Spengler reaction to form the p-carboline ring, but the initial starting materials for these two reactions are the same.
    • (1993) Heterocycles , vol.36 , pp. 2707
    • Lewin, G.1    Schaeffer, C.2    Pierre, A.3    Guilbaud, N.4    Atassi, G.5    Poisson, J.6
  • 75
    • 85010487455 scopus 로고
    • Indoles, Part 2, W. J. Houlihan, Ed., of, The Chemistry of Heterocyclic Compounds, A. Weissberger and E. C. Taylor, Eds.), New York
    • F. Troxler in Indoles, Part 2, W. J. Houlihan, Ed., (Vol. 25 of The Chemistry of Heterocyclic Compounds, A. Weissberger and E. C. Taylor, Eds.), John Wiley and Sons: New York, 1972; pp. 221-251.
    • (1972) John Wiley and Sons , vol.25 , pp. 221-251
    • Troxler, F.1
  • 80
    • 1842470985 scopus 로고
    • The, more readily removed trichloroethylcarbamate could be prepared using trichloroethyl chlo- roformate, though the yield of the corresponding tetrahydro-ß-carboline was reduced to 56%
    • E. Yamanaka, N. Shibata and S. Sakai, Heterocycles, 22, 371 (1984). The more readily removed trichloroethylcarbamate could be prepared using trichloroethyl chlo- roformate, though the yield of the corresponding tetrahydro-ß-carboline was reduced to 56%.
    • (1984) Heterocycles , vol.22 , pp. 371
    • Yamanaka, E.1    Shibata, N.2    Sakai, S.3
  • 108
    • 0023945217 scopus 로고
    • Prepared in two steps in 81% overall yield from 1-phenylsulfonylindole
    • G. W. Gribble, T. C. Barden and D. A. Johnson Tetrahedron, 44, 3195 (1988). Prepared in two steps in 81% overall yield from 1-phenylsulfonylindole
    • (1988) Tetrahedron , vol.44 , pp. 3195
    • Gribble, G.W.1    Barden, T.C.2    Johnson, D.A.3
  • 117
    • 0026690440 scopus 로고
    • P. M. F*resneda and M. Cánovas
    • P. Molina, P. M. F*resneda and M. Cánovas, Tetrahedron Lett, 33, 2891 (1992).
    • (1992) Tetrahedron Lett , vol.33 , pp. 2891
    • Molina, P.1
  • 127
    • 0025248275 scopus 로고
    • The authors suggest a mechanism for this transformation in which the aldehyde group of 279 is first converted to the corresponding dithioacetate, which then undergoes nucleophilic attack by the oxime nitrogen, displacing one of the thioacetate groups. Aromatization by loss of water and deacetylation of the thioacetate group then produces 280
    • P. H. H. Hermkens, J. H. van Maarseveen, P. L. H. M. Cobben, H. C. J. Ottenheijm, C. G. Kruse and H. W. Scheeren, Tetrahedron, 46, 833 (1990). The authors suggest a mechanism for this transformation in which the aldehyde group of 279 is first converted to the corresponding dithioacetate, which then undergoes nucleophilic attack by the oxime nitrogen, displacing one of the thioacetate groups. Aromatization by loss of water and deacetylation of the thioacetate group then produces 280.
    • (1990) Tetrahedron , vol.46 , pp. 833
    • Hermkens, P.H.H.1    Van Maarseveen, J.H.2    Cobben, P.L.H.M.3    Ottenheijm, H.C.J.4    Kruse, C.G.5    Scheeren, H.W.6
  • 134
    • 0027479342 scopus 로고
    • 5-Tributylstannyl-2-ftirancarboxaldehyde was used to introduce a furfural moiety, and phenyl- boronic acid was used to introduce a phenyl group
    • P. Rocca, F. Marsais, A. Godard and G. Quéguiner, Tetrahedron, 49, 3325 (1993). 5-Tributylstannyl-2-ftirancarboxaldehyde was used to introduce a furfural moiety, and phenyl- boronic acid was used to introduce a phenyl group.
    • (1993) Tetrahedron , vol.49 , pp. 3325
    • Rocca, P.1    Marsais, F.2    Godard, A.3    Quéguiner, G.4
  • 143
    • 0026757894 scopus 로고
    • Triazine 332b was contaminated with a small amount of the opposite regioisomer
    • S. C. Benson, J.-H. Li and J. K. Snyder, J. Org. Chem., 57, 5285 (1992). Triazine 332b was contaminated with a small amount of the opposite regioisomer.
    • (1992) J. Org. Chem. , vol.57 , pp. 5285
    • Benson, S.C.1    Li, J.-H.2    Snyder, J.K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.