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Volumn , Issue 11, 2007, Pages 1775-1779

Gold-catalyzed synthesis of 2-substituted, 2,3-disubstituted and 1,2,3-trisubstituted indoles in [bmim]BF4

Author keywords

Aza Michael addition; Gold catalysis; Hydroamination; Indoles; Ionic liquids

Indexed keywords

3 BUTEN 2 ONE; ALKENE; ANILINE DERIVATIVE; CARBENE; GOLD COMPLEX; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; IONIC LIQUID; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34447543038     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-982572     Document Type: Article
Times cited : (84)

References (56)
  • 5
    • 34447549151 scopus 로고    scopus 로고
    • Thomas, E. J, Ed, Thieme: Stuttgart
    • (b) Joule, J. A. In Science of Synthesis, Vol. 10; Thomas, E. J., Ed.; Thieme: Stuttgart, 2000, 252-261.
    • (2000) Science of Synthesis , vol.10 , pp. 252-261
    • Joule, J.A.1
  • 25
    • 30344459537 scopus 로고    scopus 로고
    • Ionic liquids IIIB: Fundamentals, Process, Challenges, and Opportunities
    • Rogers, R. D, Seddon, K. R, Eds, ACS: Washington DC
    • (a) Ionic liquids IIIB: Fundamentals, Process, Challenges, and Opportunities In ACS Symposium Series; Rogers, R. D.; Seddon, K. R., Eds.; ACS: Washington DC, 2005.
    • (2005) ACS Symposium Series
  • 40
    • 33749110100 scopus 로고    scopus 로고
    • 6 were carried out according to the procedure reported in the literature: Holbrey, J. D.; Seddon, K. R. J. Chem. Soc., Dalton Trans. 1999, 2133.
    • 6 were carried out according to the procedure reported in the literature: Holbrey, J. D.; Seddon, K. R. J. Chem. Soc., Dalton Trans. 1999, 2133.
  • 41
    • 34447511561 scopus 로고    scopus 로고
    • AuCl4 was prepared as follows: To a magnetically stirred solution of [bmim]Cl (0.0458 g, 0.263 mmol) in CH2Cl2 (5 mL) was added NaAuCl4·H2O (0.100 g, 0.263 mmol) and the reaction was allowed to stand at r.t. for 4 h. Then, the mixture was extracted with CH2Cl2 (100 mL) and H2O (2 x 50 mL, The organic layer was dried (Na2SO4) and evaporated to give [bmim]AuCl4 as a yellow powder 0.120 g
    • 4 as a yellow powder (0.120 g).
  • 42
    • 34447536800 scopus 로고    scopus 로고
    • Representative Procedure: To 2-(dec-1-ynyl)aniline (1f; 0.059 g, 0.26 mmol) in [bmim]BF4 (1 mL) was added NaAuCl 4·2H2O (0.001 g, 1 mol, The mixture was stirred at 50°C for 24 h. The mixture was diluted with Et2O (100 mL) and washed with brine. The Et2O layer was dried (Na2SO 4) and concentrated in vacuo and the residue was purified by flash chromatography on silica gel giving 2f (54 mg, 92% yield, mp 50-51°C. IR (KBr, 3413, 2923, 1457, 1408, 774 cm-1. 1H NMR (CDCl3, δ, 7.86 (br s, 1 H, 7.57 (d, J, 7.6 Hz, 1 H, 7.32 (d, J, 7.7 Hz, 1 H, 7.25 (dt, J1, 7.7 Hz, J2, 1.3 Hz, 1 H, 7.11 (dt, J1, 7.6 Hz, J2, 1.0 Hz, 1 H, 6.27 (s, 1 H, 2.78 (t, J, 7.6 Hz, 2 H, 1.75 (quin, J, 7.5 Hz, 2 H, 1.23-1.48 (m, 10 H, 0.93 t, J
    • +], 144 (41), 131 (81), 130 (100).
  • 55
    • 34447560021 scopus 로고    scopus 로고
    • 2O layer was separated. The ionic liquid layer containing the gold catalyst was pumped for several minutes and reused.
    • 2O layer was separated. The ionic liquid layer containing the gold catalyst was pumped for several minutes and reused.


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