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Volumn 2, Issue 9, 2000, Pages 1201-1204

Formation of new 5,11b-bridged isoindolo[2,1-b]isoquinolinones alkaloids through a tandem Pummerer/ π-cationic cyclization

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EID: 0000489804     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005545c     Document Type: Article
Times cited : (26)

References (41)
  • 1
    • 0001254480 scopus 로고
    • Thyagarajan, B. S., Eds., Wiley-Interscience: New York
    • (1)(a) Russell, G. A.; Mikol, G. J. In Mechanisms of Molecular Migrations; Thyagarajan, B. S., Eds., Wiley-Interscience: New York, 1968; Vol. 1, p 157.
    • (1968) Mechanisms of Molecular Migrations , vol.1 , pp. 157
    • Russell, G.A.1    Mikol, G.J.2
  • 29
    • 84998498497 scopus 로고
    • Imides 1a (90%) and Ic (94%) were obtained in another pathway, in yields of 90 and 80%, respectively, as reported in the following reference: Uchino, M.; Suzuki. K.; Sekiya, M. Chem. Pharm. Bull. 1979, 27, 1199.
    • (1979) Chem. Pharm. Bull. , vol.27 , pp. 1199
    • Uchino, M.1    Suzuki, K.2    Sekiya, M.3
  • 31
    • 85087225794 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of sulfoxides 3 and 4 have shown that sulfoxides 3a/4a and 3b/4b consist of 6.3:3.7 ratio while for 3c/4c, it was of 5.9:4.1.
  • 32
    • 0042075568 scopus 로고    scopus 로고
    • note
    • 2O), 6.76-8.24 (m, 16H, arom H).
  • 34
    • 0043077309 scopus 로고    scopus 로고
    • For further details on the Pummerer mechanism, see ref 1
    • For further details on the Pummerer mechanism, see ref 1.
  • 35
    • 0042576577 scopus 로고    scopus 로고
    • TFA was liberated in the medium from TFAA during Pummerer rearrangement
    • TFA was liberated in the medium from TFAA during Pummerer rearrangement.
  • 37
    • 77957077000 scopus 로고
    • Rossi, A., Eds., Academic Press: New York, Chapter 4
    • (b) Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Rossi, A., Eds., Academic Press: New York, 1988; Vol. 32, Chapter 4, p 271.
    • (1988) The Alkaloids , vol.32 , pp. 271
    • Hiemstra, H.1    Speckamp, W.N.2
  • 38
    • 0001673091 scopus 로고
    • Trost, B. M., Fleming, I., Eds., Pergamon Press: Oxford
    • Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds., Pergamon Press: Oxford, 1991; Vol. 2, p 1047.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1047
    • Hiemstra, H.1    Speckamp, W.N.2
  • 39
    • 0043077312 scopus 로고    scopus 로고
    • note
    • 2S (359.45) (mixture): C, 73.51; H, 4.76; N, 3.89. Found: C, 73.39; H, 4.66; N, 3.69.
  • 40
    • 0041574334 scopus 로고    scopus 로고
    • note
    • 16NOS (390.48): C, 79.77; H, 4.38; N, 3.58. Found: C, 79.83; H, 4.33; N, 3.51.
  • 41
    • 0043077308 scopus 로고    scopus 로고
    • We have used the same procedure, as reported in ref 22, with TFA instead TFAA and pyridine. The resulting solid was recrystallized from ethanol to give 6a as yellow needles in 58% yield
    • We have used the same procedure, as reported in ref 22, with TFA instead TFAA and pyridine. The resulting solid was recrystallized from ethanol to give 6a as yellow needles in 58% yield.


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