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Volumn 45, Issue 4, 2013, Pages 545-555

Facile synthesis of [1,2,3]-triazole-fused isoindolines, tetrahydroisoquinolines, benzoazepines and benzoazocines by palladium-copper catalysed heterocyclisation

Author keywords

1,2,3 triazoles; azide alkyne cycloaddition; bis heteroannulations; intramolecular reactions; nitrogen heterocycles

Indexed keywords

1 ,2 ,3-TRIAZOLES; AZIDE-ALKYNE CYCLOADDITION; BIS-HETEROANNULATIONS; INTRAMOLECULAR REACTIONS; NITROGEN HETEROCYCLES;

EID: 84873570152     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1316839     Document Type: Article
Times cited : (34)

References (63)
  • 19
    • 34247237682 scopus 로고    scopus 로고
    • Angew. Chem. 2007 119 1036
    • Lutz, J.-F. Angew. Chem. Int. Ed. 2007, 46, 1018; Angew. Chem. 2007, 119, 1036.
    • (2007) Lutz, J.-F. Angew. Chem. Int. Ed. , vol.46 , pp. 1018
  • 63
    • 9644285669 scopus 로고
    • Based on control experiments and known features of palladium chemistry, a plausible reaction mechanism can be envisaged. Mechanistically, the active catalytic species Pd(0) is generated in situ by dimerization, to a small extent, of acetylenic compound 8. Next, coupling of 8 with iodide 7 takes place through the Sonogashira pathway, see: Sonogashira, K.; Tohda, Y.; Haghihara, N. Tetrahedron Lett. 1975, 50, 4467; leading to the formation of intermediate σ-alkynyl azide derivative, which is then converted into products 1-4 through intramolecular [3+2] cycloaddition between azide and alkyne moieties. An alternative mechanism involving copper-assisted regioselective [3+2] cycloaddition between acetylene and azide groups of substrates 8 and 7, leading to the formation of intermediate 1,4-substituted 1,2,3-triazoles 9 (X = I), which may undergo intramolecular coupling with aryl iodide through C-H bond activation to form the products 1-4, was ruled out on the basis of control experiments.
    • (1975) Tetrahedron Lett. , vol.50 , pp. 4467
    • Sonogashira, K.1    Tohda, Y.2    Haghihara, N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.