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Volumn 61, Issue 11, 2005, Pages 2767-2778

Free radical synthesis of benzofused tricyclic β-lactams by intramolecular cyclization of 2-azetidinone-tethered haloarenes

Author keywords

Cycloaddition; Lactams; Nitrogen heterocycles; Polycycles; Radical reactions

Indexed keywords

2 AZETIDINONE DERIVATIVE; BENZYL DERIVATIVE; BETA LACTAM DERIVATIVE; PHENYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TRIBACTAM;

EID: 14344260028     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.082     Document Type: Article
Times cited : (17)

References (68)
  • 31
    • 0029988586 scopus 로고    scopus 로고
    • (b) After the initiation of our efforts, a report appeared describing the aryl radical cyclization of N-allyl-4-(o-bromophenyl)-2-azetidinones leading to 1,2-benzocarbacephams. See: B.K. Banik, G.V. Subbaraju, M.S. Manhas, and A.K. Bose Tetrahedron Lett. 37 1996 1363
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1363
    • Banik, B.K.1    Subbaraju, G.V.2    Manhas, M.S.3    Bose, A.K.4
  • 35
  • 37
    • 85030812665 scopus 로고    scopus 로고
    • note
    • 2/α-phenylethylamine complex as catalyst, using benzene as solvent and a Dean-Stark apparatus to remove the water formed during the reaction. Alternatively, N-alkylimines required in our work were smoothly prepared by the condensation of the appropriate aldehyde with the corresponding amine in dichloromethane at room temperature in the presence of anhydrous magnesium sulphate. A nearly quantitative yield of the Schiff base was obtained in all cases under these reaction conditions.
  • 38
    • 0034595608 scopus 로고    scopus 로고
    • The assignment of relative stereochemistry was determined by the observed coupling constant for methine protons H3 and H4, which is a very well established criterium in β-lactam chemistry. See, for example: (a) B. Alcaide, M.F. Aly, C. Rodríguez, and A. Rodríguez-Vicente J. Org. Chem. 65 2000 3453
    • (2000) J. Org. Chem. , vol.65 , pp. 3453
    • Alcaide, B.1    Aly, M.F.2    Rodríguez, C.3    Rodríguez-Vicente, A.4
  • 53
    • 0035831074 scopus 로고    scopus 로고
    • -1). However, we and others were able to prepare seven-membered rings by radical cyclization of β-lactam-tethered haloalkenes or alkynes. See: (a) B. Alcaide, P. Almendros, and C. Aragoncillo J. Org. Chem. 66 2001 1612
    • (2001) J. Org. Chem. , vol.66 , pp. 1612
    • Alcaide, B.1    Almendros, P.2    Aragoncillo, C.3
  • 59
    • 0036186587 scopus 로고    scopus 로고
    • For a review on the selective bond cleavage of the β-lactam nucleus, see: B. Alcaide, and P. Almendros Synlett 2002 381
    • (2002) Synlett , pp. 381
    • Alcaide, B.1    Almendros, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.