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Tetrahedron
Volumn 50, Issue 2, 1994, Pages 437-452
2-Substituted-3-acylindoles through the Palladium-Catalysed Carbonylative Cyclization of 2-Alkynyltrifluoroacetanilides with Aryl Halides and Vinyl Triflates
Author keywords

[No Author keywords available]
Indexed keywords

INDOLE DERIVATIVE; PALLADIUM COMPLEX; PRAVADOLINE;
EID: 0028118842     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)80766-3     Document Type: Article
Times cited : (138)
References (44)
  • 23
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    • Arcadi, A.; Cacchi, S.; Marinelli, F.; Pace, P.S. Synlett, in press.
  • 26
    • 84913907035 scopus 로고    scopus 로고
    • D'Ambra, T.E.; Bacon, E.R.; Bell, M.R.; Carabateas, P.M.; Eissenstat, M.A.; Kumar, V.; Mallamo, J.P.; Ward, S.J. Eur. Pat. Appl. EP 444,451.
  • 32
    • 84913913556 scopus 로고    scopus 로고
    • For example, 19c, on reaction with 6-methoxy-3,4-dihydro-1 -naphthyl triflate 20d, afforded the amide bd24 in 20% yield and the non-carbonylated 2,3-disubstituted-indole 22o in 24% yield along with other unidentified products. Formation of the amide 24 does not seem to involve the initial hydrolysis of 19e followed by the nucleophilic attack of the resultant 2-phenylethynylaniline on the σ-acylpalladium complex as it night be supposed. At least, experimental data suggest that this sequence does not represent the main reaction pathway. Indeed, 19e was found to undergo the hydrolytic cleavage of the amide bond only to a very limited extent. Treating it under usual conditions, in the absence of 20d led to its recovery in 85% yield and 2-phenylethynylaniline was detected only in trace amounts. Most probably, the formation of the amide 24 can be accounted for by the intermolecular nucleophilic attack of the nitrogen anion on the approaching σ-acylp [[Truncated]]
  • 33
    • 84913900538 scopus 로고    scopus 로고
    • In the absence of carbon monoxide, 2-n-butyl-3-benzyl indole was isolated in 13% yield at room temperature and in 47% yield at 80 °C. The N-benzyl derivative of the starting 2-alkynyltrifluoroacetanilide was isolated in 76 and 50% yield, respectively.
  • 36
    • 0000295417 scopus 로고
    • The palladium-catalyzed hydroarylation and hydrovinylation of carbon-carbon multiple bonds: New perspectives in organic synthesis
    • (1990) Pure and Applied Chemistry , vol.62 , pp. 713-722
    • Cacchi1
  • 39
    • 84913892169 scopus 로고    scopus 로고
    • 3) ° 149.3, 121.8, 118.6 (q, J = 320 Hz), 118.5, 43.0, 32.1, 28.6, 27.3, 25.4, 24.2.
  • 40
    • 0001088215 scopus 로고
    • PALLADIUM-CATALYZED REDUCTION OF VINYL TRIFLUOROMETHANESULFONATES TO ALKENES: CHOLESTA-3,5-DIENE
    • (1990) Organic Syntheses , vol.68 , pp. 138-147
    • Cacchi1    Morera2    Ortar3
  • 41
    • 84994929046 scopus 로고
    • Single-Step Improved Synthesis of Primary and Other Vinyl Trifluoromethanesulfonates
    • (1980) Synthesis , pp. 283-284
    • Stang1    Treptow2
  • 42

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.