메뉴 건너뛰기




Volumn 10, Issue 12, 2008, Pages 2609-2612

A mild, one-pot synthesis of 4-quinolones via sequential Pd-catalyzed amidation and base-promoted cyclization

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; QUINOLONE DERIVATIVE;

EID: 48849087952     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800837z     Document Type: Article
Times cited : (95)

References (33)
  • 5
    • 59949085356 scopus 로고    scopus 로고
    • There is considerable interest in quinolones as antibacterial agents: (a) Andriole, V. T. The Quinolones; Academic Press: London, 1988.
    • There is considerable interest in quinolones as antibacterial agents: (a) Andriole, V. T. The Quinolones; Academic Press: London, 1988.
  • 6
    • 59949090930 scopus 로고    scopus 로고
    • 4-Quinolones have two tautomeric forms: either the hydroxy tautomer as 4-hydroxyquinoline or the carbonyl tautomer as 4-quinolones, although these compounds exist favorably in the keto form. For more information, see: (a) Pfister-Guillouzo, G.; Guimon, C.; Frank, J.; Ellison, J.; Katritzky, A. R. Justus Liebigs Ann. Chem. 1981, 366.
    • 4-Quinolones have two tautomeric forms: either the hydroxy tautomer as 4-hydroxyquinoline or the carbonyl tautomer as 4-quinolones, although these compounds exist favorably in the keto form. For more information, see: (a) Pfister-Guillouzo, G.; Guimon, C.; Frank, J.; Ellison, J.; Katritzky, A. R. Justus Liebigs Ann. Chem. 1981, 366.
  • 12
  • 26
    • 35348846488 scopus 로고    scopus 로고
    • During the process of this study, Buchwald et al. reported a mild, two-step synthesis of 4-quinolone via Cu-catalyzed amidation followed by the base-promoted cyclization. The substrate scope was limited to the preparation of 2-aryl-4-quinolones: (a) Jones, A. P.; Anderson, K. W.; Buchwald, S. L. J. Org. Chem. 2007, 72, 7968.
    • During the process of this study, Buchwald et al. reported a mild, two-step synthesis of 4-quinolone via Cu-catalyzed amidation followed by the base-promoted cyclization. The substrate scope was limited to the preparation of 2-aryl-4-quinolones: (a) Jones, A. P.; Anderson, K. W.; Buchwald, S. L. J. Org. Chem. 2007, 72, 7968.
  • 29
    • 0035200787 scopus 로고    scopus 로고
    • Xantphos has been reported to be an excellent ligand for amidation: (a) ; Kamer, P. C.; Van Leeuwen, P. W. N.; Reek, J. N. H. Acc. Chem. Res. 2001, 34, 895.
    • Xantphos has been reported to be an excellent ligand for amidation: (a) ; Kamer, P. C.; Van Leeuwen, P. W. N.; Reek, J. N. H. Acc. Chem. Res. 2001, 34, 895.
  • 32
    • 59949101965 scopus 로고    scopus 로고
    • Addition of formamide to the reaction mixture in toluene led to formation of a gel which resulted in difficult stirring
    • Addition of formamide to the reaction mixture in toluene led to formation of a gel which resulted in difficult stirring.
  • 33
    • 59949091177 scopus 로고    scopus 로고
    • However, the use of acetamide which has more than one α-protons led to lower yield of 4-quinolone due to formation of 2-quinolone. Also see ref 10
    • However, the use of acetamide which has more than one α-protons led to lower yield of 4-quinolone due to formation of 2-quinolone. Also see ref 10.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.