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Volumn 73, Issue 7, 2008, Pages 2920-2923

Synthesis of fused 4,5-disubstituted indole ring systems by intramolecular friedel-crafts acylation of 4-substituted indoles

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; CYCLIZATION; FRIEDEL-CRAFTS REACTION; SYNTHESIS (CHEMICAL);

EID: 41649097012     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702591p     Document Type: Article
Times cited : (38)

References (26)
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    • Isolation of ambiguine H: Smitka, T. A.; Bonjouklian, R.; Doolin, L.; Jones, N. D.; Deeter, J. B. J. Org. Chem. 1992, 57, 857-861.
    • Isolation of ambiguine H: Smitka, T. A.; Bonjouklian, R.; Doolin, L.; Jones, N. D.; Deeter, J. B. J. Org. Chem. 1992, 57, 857-861.
  • 3
    • 0000542715 scopus 로고    scopus 로고
    • Isolation of lolicine A: Munday-Finch, S. C.; Wilkins, A. L.; Miles, C. O. J. Agric. Food Chem. 1998, 46, 590-598.
    • Isolation of lolicine A: Munday-Finch, S. C.; Wilkins, A. L.; Miles, C. O. J. Agric. Food Chem. 1998, 46, 590-598.
  • 4
    • 0242562365 scopus 로고    scopus 로고
    • Examples of FC alkylation of 4-substituted indoles: (a) Natsume, M.; Muratake, H. Tetrahedron Lett. 1989, 30, 1815-1818.
    • Examples of FC alkylation of 4-substituted indoles: (a) Natsume, M.; Muratake, H. Tetrahedron Lett. 1989, 30, 1815-1818.
  • 6
    • 0742321843 scopus 로고    scopus 로고
    • A related anionic cyclization of a 4-substituted indole to the 3-position was reported in a total synthesis of lysergic acid: Hendrickson, J. B.; Wang, J. Org. Lett. 2004, 6, 3-5.
    • A related anionic cyclization of a 4-substituted indole to the 3-position was reported in a total synthesis of lysergic acid: Hendrickson, J. B.; Wang, J. Org. Lett. 2004, 6, 3-5.
  • 8
    • 7844223548 scopus 로고    scopus 로고
    • Spadoni, G.; Balsamini, C.; Diamantini, G.; Di, Giacomo, B.; Tarzia, G.; Mor, M.; Plazzi, P. V.; Rivara, S.; Lucini, V.; Nonno, R.; Pannacci, M.; Fraschini, F.; Stankov, B. M. J. Med. Chem. 1997, 40, 1990-2002.
    • Spadoni, G.; Balsamini, C.; Diamantini, G.; Di, Giacomo, B.; Tarzia, G.; Mor, M.; Plazzi, P. V.; Rivara, S.; Lucini, V.; Nonno, R.; Pannacci, M.; Fraschini, F.; Stankov, B. M. J. Med. Chem. 1997, 40, 1990-2002.
  • 9
    • 0142120761 scopus 로고    scopus 로고
    • For an example of cyclization from the 3- to the 4-position of indole, see
    • For an example of cyclization from the 3- to the 4-position of indole, see: Komoda, T.; Nakatsuka, S. Heterocycl. Commun. 2003, 9, 119-122.
    • (2003) Heterocycl. Commun , vol.9 , pp. 119-122
    • Komoda, T.1    Nakatsuka, S.2
  • 10
    • 41649120425 scopus 로고    scopus 로고
    • Int. Patent WO2004101767
    • Boger, D. L. Int. Patent WO2004101767, 2004.
    • (2004)
    • Boger, D.L.1
  • 21
    • 41649114865 scopus 로고    scopus 로고
    • The position of acylation was determined unambiguously based on the disappearance of the signal for the C-3 proton and 1H-1H COSY correlations
    • 1H COSY correlations.
  • 22
    • 41649106745 scopus 로고    scopus 로고
    • For example, N-Ns indole 9 is rapidly (3 h) and quantitively deprotected by aqueous LiOH in DMF or 1,4-dioxane at rt.
    • For example, N-Ns indole 9 is rapidly (3 h) and quantitively deprotected by aqueous LiOH in DMF or 1,4-dioxane at rt.
  • 26
    • 33745711836 scopus 로고    scopus 로고
    • The only other reported route to these tetralones was disclosed by Kerr, who prepared an acyclic 4,5-disubstituted indole and built the tetralone by a clever domino process involving the non-aromatic portions of the molecule. See: England, D. B.; Magolan, J.; Kerr, M. A. Org. Lett. 2006, 8, 2209-2212.
    • The only other reported route to these tetralones was disclosed by Kerr, who prepared an acyclic 4,5-disubstituted indole and built the tetralone by a clever domino process involving the non-aromatic portions of the molecule. See: England, D. B.; Magolan, J.; Kerr, M. A. Org. Lett. 2006, 8, 2209-2212.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.