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Volumn 50, Issue 17, 2009, Pages 1920-1923

Ring opening of aziridines with ortho-bromophenyl metal reagents: synthesis of 2-substituted indolines

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; HALOGEN; INDOLE DERIVATIVE; LITHIUM; PHENETHYLAMINE DERIVATIVE;

EID: 61749099483     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.047     Document Type: Article
Times cited : (16)

References (46)
  • 4
    • 0003655764 scopus 로고    scopus 로고
    • Cordell G.A. (Ed), Academic Press, San Diego
    • In: Cordell G.A. (Ed). The Alkaloids: Chemistry and Biology Vol. 50 (1998), Academic Press, San Diego
    • (1998) The Alkaloids: Chemistry and Biology , vol.50
  • 9
    • 51649124289 scopus 로고    scopus 로고
    • and references cited therein
    • Minatti A., and Buchwald S.L. Org. Lett. 10 (2008) 2721-2724 and references cited therein
    • (2008) Org. Lett. , vol.10 , pp. 2721-2724
    • Minatti, A.1    Buchwald, S.L.2
  • 19
    • 0033800394 scopus 로고    scopus 로고
    • For reviews, see:
    • For reviews, see:. McCoull W., and Davis F.A. Synthesis 10 (2000) 1347-1365
    • (2000) Synthesis , vol.10 , pp. 1347-1365
    • McCoull, W.1    Davis, F.A.2
  • 20
    • 1542375289 scopus 로고    scopus 로고
    • Hu X.E. Tetrahedron 60 (2004) 2701-2743
    • (2004) Tetrahedron , vol.60 , pp. 2701-2743
    • Hu, X.E.1
  • 44
    • 33744928097 scopus 로고    scopus 로고
    • For an example of a reaction between a 2,6-dibromophenyllithium species and an epoxide using toluene as solvent, see:
    • For an example of a reaction between a 2,6-dibromophenyllithium species and an epoxide using toluene as solvent, see:. Okano K., Tokuyama H., and Fukuyama T. J. Am. Chem. Soc. 128 (2006) 7136-7137
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 7136-7137
    • Okano, K.1    Tokuyama, H.2    Fukuyama, T.3
  • 45
    • 33644638474 scopus 로고    scopus 로고
    • Aryl iodides were generated via deprotonation of the corresponding 1,3-dihalobenzenes with LDA and quenching of the aryllithium intermediate with iodine. For the syntheses of 1-bromo-3-chloro-2-iodobenzene and 1-bromo-3-fluoro-2-iodobenzene, the aryllithium intermediate was treated with zinc chloride prior to the iodine quench, according to the procedure of:
    • Aryl iodides were generated via deprotonation of the corresponding 1,3-dihalobenzenes with LDA and quenching of the aryllithium intermediate with iodine. For the syntheses of 1-bromo-3-chloro-2-iodobenzene and 1-bromo-3-fluoro-2-iodobenzene, the aryllithium intermediate was treated with zinc chloride prior to the iodine quench, according to the procedure of:. Menzel K., Fisher E.L., DiMichele L., Frantz D.E., Nelson T.D., and Kress M.H. J. Org. Chem. 71 (2006) 2188-2191
    • (2006) J. Org. Chem. , vol.71 , pp. 2188-2191
    • Menzel, K.1    Fisher, E.L.2    DiMichele, L.3    Frantz, D.E.4    Nelson, T.D.5    Kress, M.H.6
  • 46
    • 61749086951 scopus 로고    scopus 로고
    • note
    • 6, 23 °C) δ ppm 7.58 (d, J = 7.9 Hz, 2H), 7.15-7.28 (m, 6H), 7.04 (t, J = 8.1 Hz, 1H), 6.67 (d, J = 9.5 Hz, 1H), 4.06-4.16 (m, 1H), 3.15 (dd, J = 13.4, 9.5 Hz, 1H), 3.03 (dd, J = 13.4, 4.6 Hz, 1H), 2.91 (dd, J = 13.7, 9.5 Hz, 1H), 2.72 (dd, J = 13.6, 5.3 Hz, 1H), 1.17 (s, 9H).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.