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Beilstein J. Org. Chem. 2024, 20, 17–24, doi:10.3762/bjoc.20.3
Graphical Abstract
Scheme 1: Synthesis of heteroaryl amidines.
Figure 1: Structures of starting compounds.
Scheme 2: Scope of 3,3-diaminoacrylonitriles 1 and heterocyclic azides 2. Reaction conditions: 1 (0.5 mmol), 2...
Scheme 3: Proposed mechanism for the formation of triazoles 3.
Beilstein J. Org. Chem. 2023, 19, 1191–1197, doi:10.3762/bjoc.19.87
Figure 1: Examples of bioactive pyrazoles for the protection of cultivated plants and drugs containing a thio...
Scheme 1: Syntheses of 4,5-diamino- and 4-thiocarbamoyl-5-aminopyrazoles.
Figure 2: Structures of starting materials.
Scheme 2: Synthesis of 3,5-diaminopyrazoles 4а–с and thiocarbamoyl-NH-pyrazoles 5a–e. Reaction conditions: 1a–...
Scheme 3: Synthesis of 1-aryl-5-amino-4-thiocarbamoylpyrazoles 6a–f. Reaction conditions: 2a–d (1 mmol), 3b,c...
Scheme 4: Synthesis of 1-sulfonylpyrazoles 7a–j and 1-benzoylpyrazole 7k. Conditions for 7a–j: 2b,d,e (1 mmol...
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 ...