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Volumn , Issue 3, 2004, Pages 535-545

Diastereo- and Enantioselective Synthesis of Novel β -Lactam-Containing 1,4-Benzodiazepines through a Ketene-Imine Cycloaddition Reaction

Author keywords

Benzodiazepines; Cycloaddition; Ketenes; Ketimines; Lactams

Indexed keywords

BENZODIAZEPINE DERIVATIVE; BETA LACTAM; DIAZEPAM DERIVATIVE; IMINE; KETENE DERIVATIVE; NEW DRUG;

EID: 1242263431     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300447     Document Type: Article
Times cited : (26)

References (50)
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    • Just a few examples of Staudinger reactions involving ketimines have been previously described, apart from the reaction described in ref. [13]. [15a] J. W. Skiles, D. McNeil, Tetrahedron Lett. 1990, 31, 7277.
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    • note
    • The other methylene proton at δ = 3.83 (d, J = 13.6 Hz) only correlates with the carbonyl carbon atoms.
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    • note
    • At the magnetic field used (7 T) the chemical shift difference between the amide carbon atoms was too small (Δδ = 0.024 ppm, 1.8 Hz) to allow for their unequivocal assignment.
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    • note
    • The correlation of this carbon with the proton of the chlorobenzene ring appearing at δ = 7.16 ppm (d, J = 13.6 Hz) allows its assignment.
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    • A similar stereochemical result has been reported in the Staudinger reaction of cyclic aldimines: B. Alcaide, A. Rodríguez-Vicente, Tetrahedron. Lett. 1999, 40, 2005-2006.
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    • note
    • 1H NMR spectrum of compound 2 h measured at room temperature showed broad signals for the aromatic protons, which resolved into well-defined multiplets when the spectrum was acquired at 233 K. At this temperature all signals of the phenyl substituent become inequivalent. This observations are consistent with restricted rotation of the phenyl group, most probably due to steric interactions.
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    • For recent reviews of the formation of asymmetric quaternary carbon centers see: [25a] K. Fuji, Chem. Rev. 1993, 93, 2037.
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    • note
    • [25c] Palomo and co-workers (see ref. [15c]) have reported the application of [2+2] cycloaddition reactions to the construction of quaternary stereocenters.
  • 43
    • 1242271883 scopus 로고    scopus 로고
    • note
    • 13C, DEPT, and 2D HMQC, HMBC and NOESY NMR spectra.
  • 44
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    • note
    • The diastereotopic methylene protons of the benzyloxy groups showed three correlations in the HMBC spectrum: with the quaternary carbons corresponding to the carbamate and the ipso carbon, and with the ortho carbons of the phenyl ring. The protons linked to these carbons were assigned from their correlations observed in the HMQC spectrum: for the pair of protons at δ = 4.19 ppm and 4.81 ppm (J = 12.2 Hz), the ortho protons of the phenyl ring appear at δ = 7.23 ppm, while for those at δ = 4.67 and 4.84 ppm (J = 12.6 Hz) the corresponding ortho protons were identified as a multiplet at δ = 7.03 ppm.
  • 45
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    • note
    • The N-nitroso derivative 4 was prepared as described in ref.[4b].
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    • G. I. Georg (Ed.), VCH Publishers, Inc., New York
    • See, for example, The Organic Chemistry of β-Lactams, G. I. Georg (Ed.), VCH Publishers, Inc., New York, 1993, p. 303-306.
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    • BRUKER SHELXTL-PC: G. M. Sheldrick, University of Göttingen, Germany, 1997
    • BRUKER SHELXTL-PC: G. M. Sheldrick, University of Göttingen, Germany, 1997.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.