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Volumn 5, Issue 24, 2003, Pages 4653-4656

Convenient Access to Polysubstituted 1-Indanones by Sc(OTf) 3-Catalyzed Intramolecular Friedel-Crafts Acylation of Benzyl Meldrum's Acid Derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ACID; INDANONE DERIVATIVE; SCANDIUM;

EID: 0348041996     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035817m     Document Type: Article
Times cited : (81)

References (33)
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    • Heaney, H.1
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    • For rare earth triflate catalysts in the intramolecular Friedel-Crafts reaction of aromatics with carboxylic acids, see: (a) Cui, D.-M.; Kawamura, M.; Shimada, S.; Hayashi, T.; Tanaka, M. Tetrahedron Lett. 2003, 44, 4007-4010. For an example of protic acid-catalyzed Friedel-Crafts acylation, see: (b) Yamato, T.; Hideshima, C.; Prakash, G. K. S.; Olah, G. A. J. Org. Chem. 1991, 56, 3955-3957.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 4007-4010
    • Cui, D.-M.1    Kawamura, M.2    Shimada, S.3    Hayashi, T.4    Tanaka, M.5
  • 8
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    • For rare earth triflate catalysts in the intramolecular Friedel-Crafts reaction of aromatics with carboxylic acids, see: (a) Cui, D.-M.; Kawamura, M.; Shimada, S.; Hayashi, T.; Tanaka, M. Tetrahedron Lett. 2003, 44, 4007-4010. For an example of protic acid-catalyzed Friedel-Crafts acylation, see: (b) Yamato, T.; Hideshima, C.; Prakash, G. K. S.; Olah, G. A. J. Org. Chem. 1991, 56, 3955-3957.
    • (1991) J. Org. Chem. , vol.56 , pp. 3955-3957
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  • 12
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    • The pyrolysis of 2,2-dimethyl-5-phenoxy-1,3-dioxane-4,6-dione at 450°C provides a small amount of benzofuran-2(3H)-one via a proposed phenoxyketene intermediate; see: Crow, W. D.; McNab, H. Aust. J. Chem. 1979, 32, 111-121.
    • (1979) Aust. J. Chem. , vol.32 , pp. 111-121
    • Crow, W.D.1    McNab, H.2
  • 13
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    • For other reductive alkylation procedures, see: (a) Huang, X.; Xie, L. Synth. Commun. 1986, 16, 1701-1707. (b) Hrubowchak, D. M.; Smith, F. X. Tetrahedron Lett. 1983, 24, 4951-4954.
    • (1986) Synth. Commun. , vol.16 , pp. 1701-1707
    • Huang, X.1    Xie, L.2
  • 14
    • 0000629862 scopus 로고
    • For other reductive alkylation procedures, see: (a) Huang, X.; Xie, L. Synth. Commun. 1986, 16, 1701-1707. (b) Hrubowchak, D. M.; Smith, F. X. Tetrahedron Lett. 1983, 24, 4951-4954.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 4951-4954
    • Hrubowchak, D.M.1    Smith, F.X.2
  • 24
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    • note
    • 1H NMR analysis of the crude reaction mixture showed no decomposition of 1-indanone or formation of aldol products.
  • 30
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    • For intermolecular Friedel-Crafts arylation of ketenes, see: (b) Williams, J. W.; Osborn, J. M. J. Am. Chem. Soc. 1939, 61, 3438-3439. (c) Hurd, C. J. Am. Chem. Soc. 1925, 47, 2777-2780.
    • (1939) J. Am. Chem. Soc. , vol.61 , pp. 3438-3439
    • Williams, J.W.1    Osborn, J.M.2
  • 31
    • 0343203255 scopus 로고
    • For intermolecular Friedel-Crafts arylation of ketenes, see: (b) Williams, J. W.; Osborn, J. M. J. Am. Chem. Soc. 1939, 61, 3438-3439. (c) Hurd, C. J. Am. Chem. Soc. 1925, 47, 2777-2780.
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    • note
    • 3, the starting material was quantitatively recovered.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.