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Volumn 11, Issue 19, 2009, Pages 4262-4265

Iron trichloride-promoted cyclization of o-alkynylaryl lsocyanates: synthesis of 3-(chloromethylene)oxindoles

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE; FERRIC CHLORIDE; FERRIC ION; INDOLE DERIVATIVE; ISOCYANIC ACID DERIVATIVE;

EID: 70350137303     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9014877     Document Type: Article
Times cited : (58)

References (67)
  • 29
    • 70350183242 scopus 로고    scopus 로고
    • (Boehringer Ingelheim. Int.) WO2007122219 Al, Nov 1
    • (b) Treu, M.; Mantoulidis, A.; Tontsch-Grunt, U. (Boehringer Ingelheim. Int.) WO2007122219 Al, Nov 1, 2007.
    • (2007)
    • Treu, M.1    Mantoulidis, A.2    Tontsch-Grunt, U.3
  • 30
    • 70350175600 scopus 로고    scopus 로고
    • (Boehringer Ingelheim Int.) US20050203104 Al, Sep 15
    • (c) Heckel, A.; Roth, G. J.; Joerg, K.; Hoerer, S.; Uphues, I. (Boehringer Ingelheim Int.) US20050203104 Al, Sep 15, 2005.
    • (2005)
    • Heckel, A.1    Roth, G.J.2    Joerg, K.3    Hoerer, S.4    Uphues, I.5
  • 33
  • 52
  • 59
    • 70350197508 scopus 로고    scopus 로고
    • note
    • 1H NMR. The chemical shift of the aromatic proton H4 serves as a reliable diagnostic for the configurational assignment; see the Supporting Information.
  • 60
    • 70350201998 scopus 로고    scopus 로고
    • See the Supporting Information
    • See the Supporting Information.
  • 61
    • 70350201999 scopus 로고    scopus 로고
    • note
    • A few examples of such reactions have been previously reported, with 3-(chlorometh.ylene)oxindoles bearing an acyl group on the nitrogen, by heating with an amine. Enol ethers derived from 3-acyloxindoles have been more extensively used as substrates.
  • 63
    • 70350186553 scopus 로고    scopus 로고
    • note
    • Treatment of la under similar conditions [piperidine (2 equiv), EtOH, microwave, 150 °C, 0.3 h] only led to the corresponding ethyl carbamate (55%) and urea (45%) resulting from addition of ethanol and piperidine, respectively, to the isocyanate.
  • 64
    • 70350210583 scopus 로고    scopus 로고
    • note
    • The chemical shift of the oxindole proton H4 (5.32-6.30 ppm) supported the Z configuration of those compounds, and the configuration of 14 was unambiguously confirmed by NMR (NOE).
  • 67
    • 70350183237 scopus 로고    scopus 로고
    • note
    • max = 511 nm).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.