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Volumn 11, Issue 4, 2009, Pages 1007-1010

Indolynes as electrophilic indole surrogates: Fundamental reactivity and synthetic applications

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

EID: 62749141270     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802958a     Document Type: Article
Times cited : (84)

References (45)
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    • Pyrroles and Their Benzoderivatives: Synthesis and Applications
    • Katritzky, A. R, Rees, C. W, Eds, Pergamon Press: Oxford, UK
    • (b) Sundberg, R. J. Pyrroles and Their Benzoderivatives: Synthesis and Applications. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, UK, 1984; Vol. 4, pp 313-376.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 313-376
    • Sundberg, R.J.1
  • 4
    • 64349095640 scopus 로고    scopus 로고
    • Joule, J. A. Indole and its Derivatives. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Thomas, E. J., Ed.; George Thieme Verlag: Stuttgart, Germany, 2000; Category 2, 10, Chapter 10.13.
    • (d) Joule, J. A. Indole and its Derivatives. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Thomas, E. J., Ed.; George Thieme Verlag: Stuttgart, Germany, 2000; Category 2, Vol. 10, Chapter 10.13.
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    • 0003911273 scopus 로고    scopus 로고
    • MDL Information Systems Inc, San Leandro, CA
    • (3) MDL Drug Data Report; MDL Information Systems Inc.: San Leandro, CA.
    • MDL Drug Data Report
  • 7
    • 0027461856 scopus 로고
    • For the activation of indoles with stoichiometric chromium, see: a
    • (4) For the activation of indoles with stoichiometric chromium, see: (a) Semmelhack, M. F.; Rhee, H. Tetrahedron Lett. 1993, 34, 1399-1402.
    • (1993) Tetrahedron Lett , vol.34 , pp. 1399-1402
    • Semmelhack, M.F.1    Rhee, H.2
  • 8
    • 0027279339 scopus 로고
    • For the Pd-catalyzed enolate arylations of indoles, see
    • (b) Semmelhack, M. F.; Knochel, P.; Singleton, T. Tetrahedron Lett. 1993, 34, 5051-5054. For the Pd-catalyzed enolate arylations of indoles, see:
    • (1993) Tetrahedron Lett , vol.34 , pp. 5051-5054
    • Semmelhack, M.F.1    Knochel, P.2    Singleton, T.3
  • 11
    • 0006982548 scopus 로고
    • For reviews regarding heteroaromatic arynes, see: a
    • (5) For reviews regarding heteroaromatic arynes, see: (a) Reinecke, M. G. Tetrahedron 1982, 38, 427-498.
    • (1982) Tetrahedron , vol.38 , pp. 427-498
    • Reinecke, M.G.1
  • 13
    • 0037415520 scopus 로고    scopus 로고
    • For recent reviews regarding aryne chemistry and synthetic applications, see: a
    • (6) For recent reviews regarding aryne chemistry and synthetic applications, see: (a) Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701-730.
    • (2003) Tetrahedron , vol.59 , pp. 701-730
    • Pellissier, H.1    Santelli, M.2
  • 23
    • 64349085214 scopus 로고    scopus 로고
    • Attempts to synthesize 2, 3-indolynes have been met without success; see: (a) Muller, H. Dissertation, University of Heidelberg, 1964.
    • (9) Attempts to synthesize 2, 3-indolynes have been met without success; see: (a) Muller, H. Dissertation, University of Heidelberg, 1964.
  • 26
    • 64349107503 scopus 로고    scopus 로고
    • See also ref 5a
    • See also ref 5a.
  • 27
    • 0037241494 scopus 로고    scopus 로고
    • For the nucleophilicity of N-methylindole, see: Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77.
    • (10) For the nucleophilicity of N-methylindole, see: Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77.
  • 28
    • 64349094245 scopus 로고    scopus 로고
    • During preparation of this manuscript, Buszek and co-workers reported the synthesis of C3-substituted indolyl silyltriflates using a Fischer indolization strategy; see ref 8b.
    • (11) During preparation of this manuscript, Buszek and co-workers reported the synthesis of C3-substituted indolyl silyltriflates using a Fischer indolization strategy; see ref 8b.
  • 30
    • 64349084069 scopus 로고    scopus 로고
    • Challenges are primarily associated with the acidity of the C2 hydrogen and the electron-rich nature of the indole ring (e.g., undesired reactivity at C3 and propensity to undergo protodesilylation at C4).
    • (13) Challenges are primarily associated with the acidity of the C2 hydrogen and the electron-rich nature of the indole ring (e.g., undesired reactivity at C3 and propensity to undergo protodesilylation at C4).
  • 33
    • 64349115340 scopus 로고    scopus 로고
    • 5-Hydroxyindoles can also be readily prepared by the classic Nenitzescu indole synthesis; for a review, see: Allen, G. R. Org. React. 1973, 20, 337-454.
    • (15) 5-Hydroxyindoles can also be readily prepared by the classic Nenitzescu indole synthesis; for a review, see: Allen, G. R. Org. React. 1973, 20, 337-454.
  • 36
    • 0028903040 scopus 로고    scopus 로고
    • For the selective C4 lithiation of a related N-silylated substrate, see: Griffen, E. J.; Roe, D. G.; Snieckus, V. J. Org. Chem. 1995, 60, 1484-1485.
    • (17) For the selective C4 lithiation of a related N-silylated substrate, see: Griffen, E. J.; Roe, D. G.; Snieckus, V. J. Org. Chem. 1995, 60, 1484-1485.
  • 37
  • 38
    • 64349098954 scopus 로고    scopus 로고
    • Cleavage of the carbamate of 16 was routinely accompanied by loss of the C4 silyl substituent under a variety of reaction conditions.
    • (19) Cleavage of the carbamate of 16 was routinely accompanied by loss of the C4 silyl substituent under a variety of reaction conditions.
  • 45
    • 64349122561 scopus 로고    scopus 로고
    • See the Supporting Informationfor details
    • (25) See the Supporting Informationfor details.


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