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Volumn , Issue 8, 2009, Pages 1245-1250

Polysubstituted quinolines from 2-alkynylanilines and α,β-ynones through a sequential conjugate addition-cyclization process

Author keywords

, ynones; 2 alkynylanilines; Cyclization; Enaminones; Quinolines

Indexed keywords

ANILINE DERIVATIVE; QUINOLONE DERIVATIVE;

EID: 67649380761     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1216734     Document Type: Article
Times cited : (20)

References (34)
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    • For some recent reviews, see:
    • For some recent reviews, see: (a) Sikorski, J. A. J. Med. Chem. 2006, 49, 1.
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  • 12
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    • note
    • Conjugate additions of 2-(alkynyl)anilines to 1,3-diphenylpropynones (MeOH, 120°C) were carried out using a Carousel Tube Reaction (Radley Discovery).
  • 13
    • 67649368423 scopus 로고    scopus 로고
    • note
    • Enaminones 3 can also be prepared by treating the conjugate addition products derived from 2-iodonilines and 1,3-diarylpropynones with terminal alkynes. Using this procedure, 3a, 3q, and 3r were isolated in 77%, 74%, and 70% overall yields, respectively. This protocol, however, appeared less suited for the development of a sequential process that would omit the isolation of the enaminone intermediates (Scheme 4). (Chemical Equation Presented)
  • 14
    • 0001628407 scopus 로고
    • For some selected references on the transition-metal-catalyzed cyclization of 2-(alkynyl)anilines and -anilides, see: (Pd and Au)
    • For some selected references on the transition-metal-catalyzed cyclization of 2-(alkynyl)anilines and -anilides, see: (a) (Pd and Au) Iritani, K.; Matsubara, S.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1799.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 1799
    • Iritani, K.1    Matsubara, S.2    Utimoto, K.3
  • 15
    • 0242712817 scopus 로고    scopus 로고
    • While the manuscript was in preparation, an indium-catalyzed cyclization of β-enamino esters [prepared from β-keto esters and 2-(alkynyl)anilines] to N-vinylic indoles was described
    • (b) (Cu) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843.
    • (2003) Org. Lett. , vol.5 , pp. 3843
    • Cacchi, S.1    Fabrizi, G.2    Parisi, L.M.3
  • 16
    • 64549091509 scopus 로고    scopus 로고
    • While the manuscript was in preparation, an indium-catalyzed cyclization of β-enamino esters [prepared from β-keto esters and 2-(alkynyl)anilines] to N-vinylic indoles was described:
    • While the manuscript was in preparation, an indium-catalyzed cyclization of β-enamino esters [prepared from β-keto esters and 2-(alkynyl)anilines] to N-vinylic indoles was described: (c) Murai, K.; Hayashi, S.; Takaichi, N.; Kita, Y.; Fujioka, H. J. Org. Chem. 2009, 74, 1418.
    • (2009) J. Org. Chem. , vol.74 , pp. 1418
    • Murai, K.1    Hayashi, S.2    Takaichi, N.3    Kita, Y.4    Fujioka, H.5
  • 22
    • 67649368422 scopus 로고    scopus 로고
    • note
    • 21NO:C, 87.19; H, 5.30. Found: C, 87.25; H, 5.36.
  • 23
    • 67649323759 scopus 로고    scopus 로고
    • note
    • 2: C, 77.66; H, 4.78. Found: C, 77.52; H, 4.70.
  • 25
    • 14844347928 scopus 로고    scopus 로고
    • For other selected references, see:
    • For other selected references, see: (b) Mitscher, L. A. Chem. Rev. 2005, 105, 559.
    • (2005) Chem. Rev. , vol.105 , pp. 559
    • Mitscher, L.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.