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Volumn 3, Issue 12, 2001, Pages 1849-1851

Synthesis of β-lactams from diazoketones and imines: The use of microwave irradiation

Author keywords

[No Author keywords available]

Indexed keywords

AZO COMPOUND; BETA LACTAM; IMINE; KETONE;

EID: 0035859335     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015891+     Document Type: Article
Times cited : (77)

References (42)
  • 4
    • 0041327459 scopus 로고    scopus 로고
    • Diederichsen, U., Lindhorst, T. K., Westermann, B., Wessjohann, L., Eds.; Wiley-VCH: Weinheim
    • (d) Podlech, J.; Linder, M. R. In Bioorganic Chemistry - Highlights and New Aspects: Diederichsen, U., Lindhorst, T. K., Westermann, B., Wessjohann, L., Eds.; Wiley-VCH: Weinheim, 1999; p 43.
    • (1999) Bioorganic Chemistry - Highlights and New Aspects , pp. 43
    • Podlech, J.1    Linder, M.R.2
  • 9
    • 0004030275 scopus 로고
    • Page, M. I., Ed.; Blackie Academic & Professional: London
    • The Chemistry of β-Lactams; Page, M. I., Ed.; Blackie Academic & Professional: London, 1992.
    • (1992) The Chemistry of β-Lactams
  • 22
    • 0007100175 scopus 로고    scopus 로고
    • von Eldik, R., Hubbard, C. D., Eds.; John Wiley & Sons/Spektrum Akademischer Verlag: New York
    • (i) Mingos, D. M. P.; Whittaker, A. G. In Chemistry Under Extreme or Non-Classical Conditions; von Eldik, R., Hubbard, C. D., Eds.; John Wiley & Sons/Spektrum Akademischer Verlag: New York, 1997; p 479.
    • (1997) Chemistry Under Extreme or Non-classical Conditions , pp. 479
    • Mingos, D.M.P.1    Whittaker, A.G.2
  • 33
    • 0041827983 scopus 로고    scopus 로고
    • note
    • We assume that this side product is formed by hydrolysis of the iminium enolate depicted in Scheme 3, although it is not clear at what stage in the reaction this hydrolysis occurs.
  • 34
    • 85082932515 scopus 로고
    • Diazoketones were prepared as described in refs 1 b and 2c. Imines derived from aromatic aldehydes were prepared according to Texier-Boullet, F. Synthesis 1985, 679. Imines derived from acrolein or crotonaldehyde were prepared analogously, but were distilled prior to use.
    • (1985) Synthesis , pp. 679
    • Texier-Boullet, F.1
  • 35
    • 0042328921 scopus 로고    scopus 로고
    • note
    • The MW experiments were performed in an MLS-ETHOS 1600 apparatus (MLS GmbH) using a flask equipped with a reflux condenser (mounted outside the apparatus) or in a Teflon autoclave (100 mL). A control and monitoring software (ETHOS PC98) was used, and the temperature was monitored via a temperature sensor.
  • 36
    • 0042328920 scopus 로고    scopus 로고
    • Patai, S., Ed.; John Wiley & Sons: Chichester
    • Commercially available crotonaldehyde as used for imine formation contained ∼4% Z-isomer, which was not separated before use. An E → Z isomerization at elevated temperatures has been reported: Slayden, S. W. In The Chemistry of Double-Bonded Functional Groups. Supplement A3. Part 1; Patai, S., Ed.; John Wiley & Sons: Chichester, 1997; p 537.
    • (1997) The Chemistry of Double-Bonded Functional Groups. Supplement A3. Part 1 , pp. 537
    • Slayden, S.W.1
  • 39
    • 0042328919 scopus 로고    scopus 로고
    • note
    • The rates of the thermal and the MW-assisted formation of β-lactam 3 have been compared. After 5 min 80% conversion for the thermal reaction and 85% for the MW reaction, respectively were detected, i.e., identical rates within the limits of experimental error. The photochemical reaction is not comparable in this context, since it is, as a result of increasing extinction, dependent on the concentration of the starting materials.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.