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Volumn 63, Issue 15, 2007, Pages 3205-3216

The use of N-sulfenylimines in the β-lactam synthon method: Staudinger reaction, oxidation of the cycloadducts and ring opening of β-lactams

Author keywords

Amino acid derivatives; N Sulfenylimines; N Thiolated lactams; Staudinger reaction

Indexed keywords

AMINO ACID DERIVATIVE; BETA AMINO ACID; BETA LACTAM DERIVATIVE; CHLORIDE; KETENE DERIVATIVE; LEWIS BASE; NITROGEN; SULFENYL BETA LACTAM; SULFONYL BETA LACTAM; SULFUR; UNCLASSIFIED DRUG;

EID: 33847664294     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.01.051     Document Type: Article
Times cited : (21)

References (55)
  • 1
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    • (1982) Chemistry and Biology of β-Lactams Antibiotics , vol.1-3
  • 3
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    • (1993) Recent Advances in the Chemistry of Anti-Infective Agents
  • 5
    • 0004030275 scopus 로고
    • Page M.I. (Ed), Chapman and Hall, London
    • In: Page M.I. (Ed). The Chemistry of β-Lactams (1992), Chapman and Hall, London
    • (1992) The Chemistry of β-Lactams
  • 6
    • 3042621839 scopus 로고    scopus 로고
    • For cholesterol absorption inhibitors, see:
    • For cholesterol absorption inhibitors, see:. Burnett D.A. Curr. Med. Chem. 11 (2004) 1873-1887
    • (2004) Curr. Med. Chem. , vol.11 , pp. 1873-1887
    • Burnett, D.A.1
  • 23
    • 33847611551 scopus 로고    scopus 로고
    • note
    • For recent mechanistic considerations about the Staudinger reaction, see Ref. 9c and references therein.
  • 24
    • 33847640163 scopus 로고    scopus 로고
    • note
    • 14
  • 33
    • 33847627070 scopus 로고    scopus 로고
    • Coantic, S. Réactivité des N-Sulfonyl-, N-Sulfinyl- et N-Sulfényl-imines dans la Réaction de Staudinger: Formation de β-Lactames N-Sulfurés et leur Utilisation pour la Synthèse de β-Amino-Acides α-Oxygénés, Thèse, Université Paul Cézanne, Marseille, 2004.
  • 37
    • 9744240952 scopus 로고    scopus 로고
    • Hydrazones as N-dialkylamino-imines are also good nucleophilic partners in Staudinger-like reactions with functionalized ketenes, see:
    • Hydrazones as N-dialkylamino-imines are also good nucleophilic partners in Staudinger-like reactions with functionalized ketenes, see:. Martin-Zamora E., Ferrete A., Llera J.M., Munoz J.M., Pappalardo R.R., Fernandez R., and Lassaletta J.M. Chem.-Eur. J. 10 (2004) 6111-6129
    • (2004) Chem.-Eur. J. , vol.10 , pp. 6111-6129
    • Martin-Zamora, E.1    Ferrete, A.2    Llera, J.M.3    Munoz, J.M.4    Pappalardo, R.R.5    Fernandez, R.6    Lassaletta, J.M.7
  • 41
    • 33847649594 scopus 로고    scopus 로고
    • note
    • 24 is formed when only 1 equiv of silver nitrate is used or when only 1 equiv of electron releasing substituted benzaldehyde is added. For reactions using an excess of aldehyde, the N-sulfenylimine is separated from bisimine by flash chromatography on silica gel.
  • 53
    • 33847609629 scopus 로고    scopus 로고
    • note
    • To our knowledge, there is no precedent in the literature for such a lack of reactivity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.