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Volumn 47, Issue 1, 2011, Pages 218-220

Gold(i)-catalyzed formation of dihydroquinolines and indoles from N-aminophenyl propargyl malonates

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROQUINOLINE DERIVATIVE; GOLD; INDOLE DERIVATIVE; MALONIC ACID DERIVATIVE; NITROMETHANE;

EID: 78649821716     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0cc00033g     Document Type: Article
Times cited : (46)

References (32)
  • 28
    • 77949395209 scopus 로고    scopus 로고
    • 2 appears to be the catalytic system of choice as it stabilizes the catalyst and leads to a rapid and generally selective formation of 15 for the series of substrates studied The 9:10 ratio slowly evolves upon prolonged reaction time. For this alkene isomerisation, see:
    • I. D. Jurberg Y. Odabachian F. Gagosz J. Am. Chem. Soc. 2010 132 3543
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 3543
    • Jurberg, I.D.1    Odabachian, Y.2    Gagosz, F.3
  • 29
    • 33645828418 scopus 로고    scopus 로고
    • Dihydroquinoline 10 was unstable in the presence of silica. A simple basic work-up followed, if necessary, by a rapid filtration through a pad of silica was used to obtain the product in pure form The malonate moiety plays multiple roles in this transformation: it induces a Thorpe-Ingold effect resulting in a more favorable cyclization while limiting the coordination of the gold catalyst with the nitrogen atom probably through steric and electronic effects The electrocyclic ring-opening of 1,2-dihydroquinolines is a rare process, see:
    • A. S. K. Hashmi M. C. Blanco E. Kurpejovic W. Frey J. W. Bats Adv. Synth. Catal. 2006 348 709
    • (2006) Adv. Synth. Catal. , vol.348 , pp. 709
    • Hashmi, A.S.K.1    Blanco, M.C.2    Kurpejovic, E.3    Frey, W.4    Bats, J.W.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.