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Beilstein J. Org. Chem. 2013, 9, 2156–2167, doi:10.3762/bjoc.9.253
Graphical Abstract
Figure 1: The six 1,5-benzodiazepinones discussed in this paper together with clobazam.
Scheme 1: Synthesis of compounds 1 and 2.
Figure 2: The X-ray structures of 3a (TUPSAZ), 5a (EFARUA). In TUPSAZ there is a disordered water molecule.
Figure 3: ORTEP plot (30% probability) of 1, showing the X-ray labeling of the asymmetric unit.
Figure 4: View of the zigzag chain formed in 1, showing the H-bond and F–F interactions.
Figure 5: ORTEP plot (20% probability) of 2, showing the X-ray labeling of the asymmetric unit.
Figure 6: Packing of 2 showing the F–F contacts along the chain (orange) and the π–π interactions that form t...
Figure 7: The different tautomers in the 1H and 1-methyl series.
Figure 8: 2-Methoxy-4-methyl-3H-1,5-benzodiazepine (7).
Figure 9: 1H–19F coupling constant values either through-bond or through-space.
Figure 10: The optimized geometry of the TS of 2a inversion.
Figure 11: Equations used to transform absolute shieldings into chemical shifts [38,39].