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Volumn 65, Issue 19, 2000, Pages 6213-6216

Cascades to substituted indoles

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; FREE RADICAL; HYDROGEN; INDOLE DERIVATIVE; ISONITRILE DERIVATIVE;

EID: 0034703408     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000831n     Document Type: Article
Times cited : (81)

References (60)
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    • For recent reviews of indole containing natural products, see: (a) Lounasmaa, M.; Tolvanen, A. Nat. Prod. Rep. 2000, 17, 175.
    • (2000) Nat. Prod. Rep. , vol.17 , pp. 175
    • Lounasmaa, M.1    Tolvanen, A.2
  • 8
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    • Houlihan, W. J., Ed.; Heterocyclic Compounds; Wiley-Interscience: New York
    • (c) Remers, W. A.; Brown, R. K. In Indoles; Houlihan, W. J., Ed.; Heterocyclic Compounds; Wiley-Interscience: New York, 1972; Part One, pp 200-203.
    • (1972) Indoles , Issue.PART ONE , pp. 200-203
    • Remers, W.A.1    Brown, R.K.2
  • 11
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    • For examples of the generation of indolenines in the presence of sensitive functionality, see ref 4
    • For examples of the generation of indolenines in the presence of sensitive functionality, see ref 4.
  • 14
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    • Curran and co-workers have developed and applied isonitrile-alkyne radical cyclizations in synthesis. See: (a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1991, 113, 2127.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 2127
    • Curran, D.P.1    Liu, H.2
  • 20
    • 0343342687 scopus 로고    scopus 로고
    • References 9, 10, 12, 13, and 27
    • (c) References 9, 10, 12, 13, and 27.
  • 22
    • 0000041025 scopus 로고    scopus 로고
    • Aryl isonitrile-alkene cyclizations have been used to generate complex indoles. See ref 12 and: (a) Kobayashi, Y.; Fukuyama, T. J. Heterocycl. Chem. 1998, 35, 1043.
    • (1998) J. Heterocycl. Chem. , vol.35 , pp. 1043
    • Kobayashi, Y.1    Fukuyama, T.2
  • 24
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    • A possible complication with the mechanism depicted in Scheme 1 is the intermolecular addition of the radical to the alkyne rather than the isonitrile. See: Leardini, R.; Nanni, D.; Zanardi, G. J. Org. Chem. 2000, 65, 2763.
    • (2000) J. Org. Chem. , vol.65 , pp. 2763
    • Leardini, R.1    Nanni, D.2    Zanardi, G.3
  • 25
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    • Ito and co-workers have demonstrated that the anionic cyclization of arylisonitriles having pendant alkynes provides quinolines. See: Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977.
    • (1999) Org. Lett. , vol.1 , pp. 1977
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  • 28
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    • -1)
    • -1).
  • 30
    • 0342907593 scopus 로고    scopus 로고
    • The protodestannylated products were more robust and thus easier to purify than the 2-stannylindoles
    • The protodestannylated products were more robust and thus easier to purify than the 2-stannylindoles.
  • 36
    • 0342473240 scopus 로고    scopus 로고
    • 10d was isolated as the 2-tributylstannylquinoline adduct. Acidic workup failed to give protodestannylated product
    • 10d was isolated as the 2-tributylstannylquinoline adduct. Acidic workup failed to give protodestannylated product.
  • 37
    • 0342907592 scopus 로고    scopus 로고
    • We have attempted to couple the intermediate indolenine with diethylamine, aniline, benzylamine, and methanol
    • We have attempted to couple the intermediate indolenine with diethylamine, aniline, benzylamine, and methanol.
  • 38
  • 40
    • 0001226141 scopus 로고
    • (a) Saegusa first demonstrated the reactivity of isonitriles with thiol radicals. See: Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118.
    • (1970) J. Org. Chem. , vol.35 , pp. 2118
    • Saegusa, T.1    Kobayashi, S.2    Ito, Y.3
  • 41
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    • More recently, Bachi and Nanni have independently coupled thiol radicals with isonitriles. See: (b) Bachi, M. D.; Balanov, A.; Bar-Ner, N. J. Org. Chem. 1994, 59, 7752.
    • (1994) J. Org. Chem. , vol.59 , pp. 7752
    • Bachi, M.D.1    Balanov, A.2    Bar-Ner, N.3
  • 43
    • 0342473239 scopus 로고    scopus 로고
    • It is not clear to us at the present time whether thiol addition to 4a (R = thioether, R′ = TMS) is occurring heterolytically or homolytically. Both would lead to bis-thiol indoles
    • It is not clear to us at the present time whether thiol addition to 4a (R = thioether, R′ = TMS) is occurring heterolytically or homolytically. Both would lead to bis-thiol indoles.
  • 44
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    • For examples of the deprotonation of thiomethylsilanes see: (a) Ager, D. J.; Cookson, R. C. Tetrahedron Lett. 1980, 21, 1677.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 1677
    • Ager, D.J.1    Cookson, R.C.2
  • 46
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    • For a review on the reductive metalation of phenyl thioethers see: Cohen, T.; Bhupathy, M. Acc. Chem. Res. 1989, 22, 152.
    • (1989) Acc. Chem. Res. , vol.22 , pp. 152
    • Cohen, T.1    Bhupathy, M.2
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    • Corey, E.J.1    Chen, Z.2
  • 53
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    • We believe that bis-thioindole 32 comes from an irreversible coupling reaction between ethanethiol and phosphonium salt 35 (Scheme 2)
    • We believe that bis-thioindole 32 comes from an irreversible coupling reaction between ethanethiol and phosphonium salt 35 (Scheme 2).
  • 59
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    • Other natural products containing spiro-fused indoles include the aspidospermine alkaloids. For example, see: Saxton, J. E. Nat. Prod. Rep. 1987, 4, 591.
    • (1987) Nat. Prod. Rep. , vol.4 , pp. 591
    • Saxton, J.E.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.