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Volumn 11, Issue 13, 2009, Pages 2796-2799

Zinc-catalyzed reactions of ethenetricarboxylates with 2- (trimethylsilylethynyl)anilines leading to bridged quinoline derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; FUSED HETEROCYCLIC RINGS; INDOLE DERIVATIVE; QUINOLINE DERIVATIVE; TRICARBOXYLIC ACID; ZINC;

EID: 67649499986     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900960q     Document Type: Article
Times cited : (29)

References (36)
  • 1
    • 84944031181 scopus 로고    scopus 로고
    • For quinolines, see: a, Katritzky, A. R, Rees, C. W, Scriven, E. F. V, Eds, Pergamon: Oxford
    • For quinolines, see: (a) Balasubramanian, M.; Keay, J. G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 5, p 245.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.5 , pp. 245
    • Balasubramanian, M.1    Keay, J.G.2
  • 3
    • 0001275286 scopus 로고    scopus 로고
    • For indoles, see: a, Katritzky, A. R, Rees, C. W, Scriven, E. F. V, Eds, Pergamon: Oxford
    • For indoles, see: (a) Gribble, G. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 5, p 207.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.5 , pp. 207
    • Gribble, G.W.1
  • 5
    • 0003593740 scopus 로고
    • The Chemistry of Heterocyclic Compounds
    • Saxton, J. E, Ed, Wiley: New York
    • (c) The Chemistry of Heterocyclic Compounds, Part 4; Vol. 25, Indoles: The Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; Wiley: New York, 1983.
    • (1983) Indoles: The Monoterpenoid Indole Alkaloids , vol.25 , Issue.PART 4
  • 7
    • 52949090063 scopus 로고    scopus 로고
    • For recent examples of synthesis of quinolines, see: a
    • For recent examples of synthesis of quinolines, see: (a) Madapa, S.; Tusi, Z.; Batra, S. Curr. Org. Chem. 2008, 12, 1116.
    • (2008) Curr. Org. Chem , vol.12 , pp. 1116
    • Madapa, S.1    Tusi, Z.2    Batra, S.3
  • 20
    • 53849121998 scopus 로고    scopus 로고
    • For recent examples of synthesis of indoles, see: a
    • For recent examples of synthesis of indoles, see: (a) Cui, S.-L.; Wang, J.; Wang, Y.-G. J. Am. Chem. Soc. 2008, 130, 13526.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 13526
    • Cui, S.-L.1    Wang, J.2    Wang, Y.-G.3
  • 28
    • 67649569805 scopus 로고    scopus 로고
    • 2 gave 4′-aminoacetophenone in 47% isolated yield. On the other hand, the reaction of (trimethylsilylethynyl)benzene did not change under the reaction conditions. The detailed mechanism of loss of TMS is under investigation.
    • 2 gave 4′-aminoacetophenone in 47% isolated yield. On the other hand, the reaction of (trimethylsilylethynyl)benzene did not change under the reaction conditions. The detailed mechanism of loss of TMS is under investigation.
  • 29
    • 67649546700 scopus 로고    scopus 로고
    • 2′-Aminoacetophenone 5 and the amine adduct C are possibly formed in situ from Zn-catalyzed water addition to the triple bond of 2-ethynylanilines. The effect of water in situ will be investigated in due course.
    • 2′-Aminoacetophenone 5 and the amine adduct C are possibly formed in situ from Zn-catalyzed water addition to the triple bond of 2-ethynylanilines. The effect of water in situ will be investigated in due course.
  • 30
    • 0001201983 scopus 로고    scopus 로고
    • Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 258.1.
    • Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 258.1.
  • 36
    • 67649570802 scopus 로고    scopus 로고
    • Typical experimental procedure (Table 1, Entry 4, To a solution of lb (107 mg, 0.39 mmol) in 1,2-dichloroethane (0.72 mL) was added 2-(trimethylsilylethynyl)aniline (2b, 74 mg, 0.39 mmol) and Zn(OTf) 2 (29 mg, 0.08 mmol, The mixture was heated at 80 °C and stirred for 3 h. The reaction mixture was cooled to 0 °C and quenched with water. The mixture was diluted with dichloromethane and then saturated aqueous NaHCO3 was added. The organic phase was extracted with dichloromethane, dried (Na2SO4, and evaporated in vacuo. The residue was purified by column chromatography over silica gel with hexane-ether as eluent to give 4a (76 mg, 58, 4a: Rf, 0.1 (hexane-ether, 1, 1, Colorless crystals; mp 124-125 °C; 1H NMR (400 MHz, CDCl3) δ (ppm) 1.02 (t, J, 7.1 Hz, 3H, 1.33 (t, J, 7.1 Hz, 3H, 1.98 (s, 3H, 3.77-4.05 (m, 1H, 4.07-4.15 (m, 1H, 4.35 q, J, 7.1 Hz, 2H
    • 6: C, 61.25; H, 5.75; N, 4.20. Found: C, 61.00; H, 5.6.1; N, 4.22.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.