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Volumn 696, Issue 1, 2011, Pages 37-41

Formation of cinnoline derivatives by a gold(I)-catalyzed hydroarylation of N-propargyl-N′-arylhydrazines

Author keywords

Cinnoline derivatives; Gold complexes; Homogeneous catalysis; Hydroarylation

Indexed keywords

ARYLHYDRAZINES; CINNOLINE; CINNOLINE DERIVATIVES; EFFICIENT SYNTHESIS; FUNCTIONALIZED; GOLD COMPLEXES; HOMOGENEOUS CATALYSIS; HYDROARYLATION; METHYL ESTERS; NITROMETHANE; PROPARGYL; REFLUXING;

EID: 78649839538     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.06.017     Document Type: Article
Times cited : (40)

References (37)
  • 3
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    • Fr Patent 1393596
    • A.G. Siegfried, Fr Patent 1393596 (1965).
    • (1965)
    • Siegfried, A.G.1
  • 4
    • 78649831597 scopus 로고    scopus 로고
    • For selected examples, see
    • For selected examples, see:
  • 10
    • 78649815665 scopus 로고    scopus 로고
    • For examples of gold(I)-catalyzed formation of quinoline derivatives following a hydroarylation process, see
    • For examples of gold(I)-catalyzed formation of quinoline derivatives following a hydroarylation process, see:
  • 16
    • 77951773016 scopus 로고    scopus 로고
    • For a recent review on hydroarylation reactions catalyzed by electrophilic metal complexes, see: P. de Mendoza, and A.M. Echavarren Pure Appl. Chem. 82 2010 801 820 For selected reviews on gold catalysis, see:
    • (2010) Pure Appl. Chem. , vol.82 , pp. 801-820
    • De Mendoza, P.1    Echavarren, A.M.2
  • 23
    • 51249100498 scopus 로고    scopus 로고
    • A. Arcadi Chem. Rev. 108 2008 3266 3325
    • (2008) Chem. Rev. , vol.108 , pp. 3266-3325
    • Arcadi, A.1
  • 26
    • 78649848560 scopus 로고    scopus 로고
    • A carbamate or a tosylamide group was not compatible with this transformation, see Ref. [5]
    • A carbamate or a tosylamide group was not compatible with this transformation, see Ref. [5].
  • 27
    • 78649887831 scopus 로고    scopus 로고
    • A very low yield of the desired quinoline derivative was obtained when the malonate group was omitted, see Ref. [5]
    • A very low yield of the desired quinoline derivative was obtained when the malonate group was omitted, see Ref. [5].
  • 28
    • 78649814145 scopus 로고    scopus 로고
    • A more favourable coordination of the nitrogen atom with the gold complex in hydrazine derivative 14 might be responsible for the higher loading of gold catalyst required (by comparison with the formation of quinoline derivatives 5, see Ref. [5])
    • A more favourable coordination of the nitrogen atom with the gold complex in hydrazine derivative 14 might be responsible for the higher loading of gold catalyst required (by comparison with the formation of quinoline derivatives 5, see Ref. [5]).
  • 29
    • 78649823127 scopus 로고    scopus 로고
    • This contrasts with our previously reported synthesis of quinoline derivatives 5 for which a partial gold-catalyzed isomerization of the exo-methylene function was generally observed, see Ref. [5]
    • This contrasts with our previously reported synthesis of quinoline derivatives 5 for which a partial gold-catalyzed isomerization of the exo-methylene function was generally observed, see Ref. [5].
  • 30
    • 78649813647 scopus 로고    scopus 로고
    • The formation of numerous unidentified by-products lacking the tert-butyl moiety was observed. For selected examples of intermolecular hydroaminations of alkynes, see
    • The formation of numerous unidentified by-products lacking the tert-butyl moiety was observed. For selected examples of intermolecular hydroaminations of alkynes, see:
  • 37
    • 78649826488 scopus 로고    scopus 로고
    • Preliminary attempts to perform the hydroarylation on substrates possessing a substituent (vinyl, phenyl, allyl) at the alkyne terminus were unsuccessful
    • Preliminary attempts to perform the hydroarylation on substrates possessing a substituent (vinyl, phenyl, allyl) at the alkyne terminus were unsuccessful.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.