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Beilstein J. Org. Chem. 2021, 17, 2321–2328, doi:10.3762/bjoc.17.150
Graphical Abstract
Figure 1: Representation of bioactive molecules and applications.
Scheme 1: Synthetic methodologies for 3-monohalooxindoles.
Scheme 2: Substrate scope of the acidolysis of isatin-derived phosphates 2 with hydrochloric acid. Standard r...
Scheme 3: Substrate scope of the acidolysis of isatin-derived phosphates 2 with hydrobromic acid. Standard re...
Scheme 4: Reduction of the substrates 2 to the corresponding oxindoles 5.
Scheme 5: Plausible reaction mechanism.
Beilstein J. Org. Chem. 2019, 15, 2623–2630, doi:10.3762/bjoc.15.255
Scheme 1: Two modes of reactions of alkynes by silver catalysis.
Scheme 2: Reactions of ynamides or ynol ethers with isoxazoles by transition metal catalysis.
Figure 1: Selected bioactive molecules containing the 5-amino-1H-pyrrole-3-carboxamide motif.
Scheme 3: Reactions of ynamide 4a with different isoxazoles 5, 7 and 8a.
Figure 2: Scope with regard to ynamide 4. All reactions were carried out with ynamide 4 (0.2 mmol), isoxazole ...
Figure 3: Scope with regard to the 5-aminoisoxazole 8 (see Figure 2). aReaction conditions: 2.0 equiv of 8e, 100 °C.
Figure 4: Molecular structure in the solid state of compound 10ad.
Scheme 4: A gram-scale experiment.
Scheme 5: Mechanistic hypotheses for Ag-catalyzed reaction of ynamide 4a with aminoisoxazole 8a.
Scheme 6: Possible reaction routes of intermediate C.