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Beilstein J. Org. Chem. 2018, 14, 2618–2626, doi:10.3762/bjoc.14.240
Graphical Abstract
Scheme 1: C–H/C–Li cross-coupling reactions of 2H-imidazole 1-oxides 1a–d and carboranyl lithium 2. The react...
Figure 1: The 1H NMR spectra of 1-(5-(4-bromophenyl)-2-ethyl-2-methyl-2H-imidazol-4-yl)-1,2-dicarba-closo-dod...
Figure 2: Fragment of the 2D 1H–13C{1H} HSQC (a) and HMBC (b) spectra of imidazolyl carborane 5d in CDCl3 at ...
Figure 3: Molecular structure of 5d. Selected bond distances (Å) and angles (deg) for molecule 1: C(3)–C(14),...
Beilstein J. Org. Chem. 2017, 13, 2535–2548, doi:10.3762/bjoc.13.250
Figure 1: (A) Adamantylated azoles and derivatives of 1,2,4-triazolo[5,1-c][1,2,4]triazine with antiviral act...
Scheme 1: Synthesis and adamantylation of 15N-labelled 13-15N2 and JHN and JCN data confirming the structures...
Scheme 2: Synthesis and adamantylation of 15N-labelled 20-15N2 and JHN and JCN data confirming the structures...
Scheme 3: Synthesis and adamantylation of 15N-labelled 23-15N2 and JHN and JCN data confirming the structure ...
Scheme 4: Isomerization of 15a in the presence of tetrazolo[1,5-b][1,2,4]triazin-7-one 13-15N2 and isotopic e...
Figure 2: 1D 15N NMR spectra of 30–70 mM 13-15N2, 15a,b-15N2, 20-15N2, 21a,b-15N2, 23-15N2 and 24-15N2 in DMS...
Figure 3: Signals of the C1' and C6 atoms in the proton-decoupled 1D 13C NMR spectra of 30–42 mM 15a,b-15N2, ...
Figure 4: Detection and quantification of the 1H-15N spin–spin interactions in compound 15a-15N2 (DMSO-d6, 45...
Figure 5: ORTEP diagrams of the X-ray structures of compounds 15a-15N2 (a) and 15b-15N2 (b). For clarity, the...
Scheme 5: Mechanism of the isomerization of compounds 15a and 15b.
Beilstein J. Org. Chem. 2016, 12, 2390–2401, doi:10.3762/bjoc.12.233
Figure 1: Biologically active isoxazoles conjugated to other azole rings.
Scheme 1: Reactions of azolyl enamines with nitrile oxides.
Figure 2: Structures of starting enamines 1 and hydroxamoyl chlorides 2.
Scheme 2: Synthesis of 4-azolylisoxazoles 4a–p from enamines 1a–e and hydroxamoyl chlorides 2a–h. Reaction co...
Figure 3: Imidazolylisoxazole 4a according to XRD data in the thermal ellipsoids of the 50% probability level....
Figure 4: Isoxazolylisoxazole 4p according to XRD data with thermal ellipsoids of 50% probability level.
Scheme 3: Plausible mechanisms for reaction of hydroxamoyl chlorides 2 with imidazolyl enamines 1a,b.
Figure 5: Geometries of enamine 1a appropriate to the calculated minima on the PES, and their relative free e...
Scheme 4: Calculated pathways for the formation of experimentally observed 3a, regioisomer 7 and isoxazoline 8...
Figure 6: Structures of the localized transition states. Lengths of the forming bonds are given in Å.
Figure 7: Summary of the calculated pathways of the cycloaddition reaction between enamine 1a and benzonitril...
Figure 8: Isosurface plots of the HOMO of enamine 1a_1 (bottom) and the LUMO of nitrile oxide 6 (top) in the ...