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Volumn 69, Issue 8, 2004, Pages 2913-2916

A Direct Access to 3-(2-Oxoalkyl)indoles via Aluminum Chloride Induced C-C Bond Formation

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; ALUMINUM COMPOUNDS; DERIVATIVES; SYNTHESIS (CHEMICAL);

EID: 1842638251     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049923t     Document Type: Article
Times cited : (23)

References (50)
  • 1
    • 1842654270 scopus 로고    scopus 로고
    • Sundberg, R. J., Ed.; Academic: London
    • Indoles; Sundberg, R. J., Ed.; Academic: London, 1996.
    • (1996) Indoles
  • 9
    • 84943388739 scopus 로고
    • Pyrroles and their Benzo Derivatives: Synthesis and Applications
    • Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford
    • (b) Sundberg, R. J. Pyrroles and their Benzo Derivatives: Synthesis and Applications. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 4, pp 313-376.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 313-376
    • Sundberg, R.J.1
  • 21
    • 26144459985 scopus 로고
    • US 2947759, Aug 2, 1960
    • (d) Robinson, R. A. US 2947759, Aug 2, 1960; Chem. Abstr. 1961, 55, 3615c.
    • (1961) Chem. Abstr. , vol.55
    • Robinson, R.A.1
  • 25
    • 1842805384 scopus 로고
    • For synthesis from 1-11a66a-tetrahydro-6-azacyclopropa[a]inden-1-yl-ethanone, see: (h) Biellmann, J. F.; Goeldner, M. P. Tetrahedron 1971, 27, 1789-1798.
    • (1971) Tetrahedron , vol.27 , pp. 1789-1798
    • Biellmann, J.F.1    Goeldner, M.P.2
  • 26
    • 0042233997 scopus 로고    scopus 로고
    • For a recent report on enantioselective Friedel-Crafts alkylation of indoles catalyzed by scandium(III) triflate-pyridyl(bis)-oxazoline complexes, see: (i) Evans, D. A.; Scheidt, K. A.; Fandrick, K. R.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780-10781.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 10780-10781
    • Evans, D.A.1    Scheidt, K.A.2    Fandrick, K.R.3    Lam, H.W.4    Wu, J.5
  • 41
    • 0038286791 scopus 로고
    • The dimeric product 5 was formed due to the reaction of 5-acetyl-3-methylindole (generated in the reaction mixture by acetylation of 3-methylindole) with the unreacted 3-methylindole in the presence of acid. For a detailed discussion on the mechanism of acid-catalyzed dimerization of 3-methylindole, see: (c) Hinman, R. L.; Shull, E. R. J. Org. Chem. 1961, 26, 2339-2342.
    • (1961) J. Org. Chem. , vol.26 , pp. 2339-2342
    • Hinman, R.L.1    Shull, E.R.2
  • 42
    • 85086489102 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra, which was found to be missing in the case of 3a.
  • 43
    • 1842805383 scopus 로고    scopus 로고
    • note
    • 11NO: C, 76.28; H, 6.40; N, 8.09. Found: C, 76.37; H, 6.25; N, 8.23.
  • 48
    • 1842654262 scopus 로고
    • Chem. Abstr. 1992, 118, 256928.
    • (1992) Chem. Abstr. , vol.118 , pp. 256928
  • 50
    • 0042791484 scopus 로고
    • Complexation of indole with a variety of Lewis acids has been reported previously; see: Schmitz-Dumount, O.; Motzkus, E. Chem. Ber. 1929, 62, 2, 466-468. See also ref 12b.
    • (1929) Chem. Ber. , vol.62 , Issue.2 , pp. 466-468
    • Schmitz-Dumount, O.1    Motzkus, E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.