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Beilstein J. Org. Chem. 2017, 13, 2569–2576, doi:10.3762/bjoc.13.253
Graphical Abstract
Scheme 1: General scheme for intramolecular heterocylization of intermediate X-ylides.
Figure 1: Thioamides 1a–e, diazoesters 2a–d and Rh(II)-catalysts used in the project.
Figure 2: The structures of compounds 4a and 3b according to the data of X-ray analysis (Olex2 plot with 50% ...
Scheme 2: Rh(II)-Catalyzed reactions of α-diazocyanoacetic ester 2d with α-cyanothioacetamides 1a–e.
Figure 3: The structure of thiophene 5c according to the data of X-ray analysis (Olex2 plot with 50% probabil...
Scheme 3: Interaction of thioacetamide 1e with dirhodium pivalate to produce complex 6e.
Figure 4: The structure of the complex 6e according to the data of X-ray analysis (Olex2 plot with 50% probab...
Scheme 4: The assumed mechanism for the formation of thiophenes 3, 5.
Scheme 5: The plausible mechanism for the formation of thiophenes 4.
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 ...