메뉴 건너뛰기




Volumn 45, Issue 42, 2006, Pages 7079-7082

Domino Cu-catalyzed C-N coupling/hydroamidation: A highly efficient synthesis of nitrogen heterocycles

Author keywords

Amidation; Copper; Domino reactions; Heterocycles; Hydroamidation

Indexed keywords

COPPER; OLEFINS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 33750623389     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602917     Document Type: Article
Times cited : (382)

References (60)
  • 4
    • 2942557280 scopus 로고    scopus 로고
    • For general reviews on the metal-catalyzed synthesis of heterocycles, see: a) I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127;
    • (2004) Chem. Rev. , vol.104 , pp. 2127
    • Nakamura, I.1    Yamamoto, Y.2
  • 12
    • 0141854366 scopus 로고    scopus 로고
    • For leading references on copper-catalyzed C-N bond-forming reactions, see: a) D. Ma, Q. Cai, H. Zhang, Org. Lett. 2003, 5, 2453;
    • (2003) Org. Lett. , vol.5 , pp. 2453
    • Ma, D.1    Cai, Q.2    Zhang, H.3
  • 26
    • 33644951667 scopus 로고    scopus 로고
    • For recent reviews and selected syntheses of pyrroles, see: a) L. Lu, G. Chen, S. Ma, Org. Lett. 2006, 8, 835;
    • (2006) Org. Lett. , vol.8 , pp. 835
    • Lu, L.1    Chen, G.2    Ma, S.3
  • 36
    • 4544235255 scopus 로고    scopus 로고
    • for the biological significance of pyrroles, see: i) A. Fürstner, Angew. Chem. 2003, 115, 3706;
    • (2003) Angew. Chem. , vol.115 , pp. 3706
    • Fürstner, A.1
  • 39
    • 33746868887 scopus 로고    scopus 로고
    • For recent syntheses of pyrazoles, see: a) T. Persson, J. Nielsen, Org. Lett. 2006, 8, 3219;
    • (2006) Org. Lett. , vol.8 , pp. 3219
    • Persson, T.1    Nielsen, J.2
  • 44
    • 85041944712 scopus 로고    scopus 로고
    • Pyrazoles as Drugs: Facts and Fantasies
    • (Eds.: O. A. Attanasi, D. Spinelli), Italian Society of Chemistry, Rome
    • for the biological significance of pyrazoles, see: f) "Pyrazoles as Drugs: Facts and Fantasies": J. Elguero, P. Goya, N. Jagerovic, A. M. S. Silva in Targets in Heterocyclic Systems - Chemistry and Properties, Vol. 6 (Eds.: O. A. Attanasi, D. Spinelli), Italian Society of Chemistry, Rome, 2002, p. 52.
    • (2002) Targets in Heterocyclic Systems - Chemistry and Properties, Vol. 6 , pp. 52
    • Elguero, J.1    Goya, P.2    Jagerovic, N.3    Silva, A.M.S.4
  • 53
    • 33750622247 scopus 로고    scopus 로고
    • note
    • Starting haloenynes were readily prepared, generally in one to three steps from commercially available starting materials. For details, see the supporting information.
  • 57
    • 33750633430 scopus 로고    scopus 로고
    • note
    • a) Pyrrole cascade: 90% conversion after 4 h, 34% pyrrole and 41% C-N coupling product;
  • 58
    • 33750614235 scopus 로고    scopus 로고
    • note
    • b) pyrazole cascade: 80% conversion after 4 h, 25 % cyclized product and 55 % C-N coupling product.
  • 60
    • 33750632955 scopus 로고    scopus 로고
    • note
    • Additionally, a control experiment was performed in which 1-(1-propynyl)cyclohexene was subjected to the reaction conditions; no traces of intermolecular hydroamidation products were detected after 24 h, thus indicating that intermolecular hydroamidation is unlikely using our protocol.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.