메뉴 건너뛰기




Volumn , Issue 20, 2005, Pages 3071-3074

Synthesis of 3,5,7-substituted indoles via heck cyclisation

Author keywords

Anilines; Heck reaction; Hydroxybenzimidazole; Indoles; Palladium

Indexed keywords

ANILINE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM;

EID: 29744454349     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-921917     Document Type: Article
Times cited : (11)

References (36)
  • 2
    • 29744434171 scopus 로고    scopus 로고
    • note
    • A search for the indole core in WDI database retrieved more than 3700 hits. See also ref. 5.
  • 7
    • 84990086006 scopus 로고
    • Review on the use of transition metals in the synthesis and functionalisation of indoles: Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113.
    • (1988) Angew. Chem., Int. Ed. Engl. , vol.27 , pp. 1113
    • Hegedus, L.S.1
  • 8
    • 0029823888 scopus 로고    scopus 로고
    • and references cited therein
    • (a) This article gives a very comprehensive overview of the challenges faced in the synthesis of 7-substituted indoles: Ezquerra, J.; Pedregal, C.; Lamas, C. J. Org. Chem. 1996, 61, 5804; and references cited therein.
    • (1996) J. Org. Chem. , vol.61 , pp. 5804
    • Ezquerra, J.1    Pedregal, C.2    Lamas, C.3
  • 11
    • 0028118842 scopus 로고
    • It is possible to functionalise the 3-position in situ, but it implies concomitant substitution at the 2-position: (a) Arcadi, A.; Cacchi, S.; Carcinelli, V.; Marinelli, F. Tetrahedron 1994, 50, 437.
    • (1994) Tetrahedron , vol.50 , pp. 437
    • Arcadi, A.1    Cacchi, S.2    Carcinelli, V.3    Marinelli, F.4
  • 22
    • 29744469048 scopus 로고    scopus 로고
    • note
    • Aniline 2 is also commercially available from Maybridge.
  • 26
    • 0000629440 scopus 로고    scopus 로고
    • Liebeskind, L. S., Ed.; JAI Press: Greenwich CT
    • (d) Jeffery, T. In Advances in Metal-Organic Chemistry, Vol. 5; Liebeskind, L. S., Ed.; JAI Press: Greenwich CT, 1996, 153-260.
    • (1996) Advances in Metal-Organic Chemistry , vol.5 , pp. 153-260
    • Jeffery, T.1
  • 29
    • 29744436275 scopus 로고    scopus 로고
    • See also ref. 13
    • (b) See also ref. 13.
  • 30
    • 29744436895 scopus 로고    scopus 로고
    • note
    • The NOE experiment proved that the stereochemistry of the exocyclic double bond is as shown in Scheme 3.
  • 32
    • 29744449376 scopus 로고    scopus 로고
    • See also ref. 9b
    • (b) See also ref. 9b.
  • 35
    • 29744443797 scopus 로고    scopus 로고
    • note
    • Removal of the TFA proved more difficult than in the case of amide 11 and was not complete after 2 d using similar conditions (deprotection of 11 takes 15 min at r.t). We therefore did not attempt the Heck cyclisation on the unprotected aniline.
  • 36
    • 29744457309 scopus 로고    scopus 로고
    • note
    • 3: 310.14377; found: 310.14372.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.