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Beilstein J. Org. Chem. 2023, 19, 1841–1848, doi:10.3762/bjoc.19.136
Graphical Abstract
Figure 1: Glutarimide-based immunomodulatory drugs (IMiDs) and CRBN ligands.
Scheme 1: Main literature approaches towards α-hetaryl glutarimides 1 (routes A and B) and new “diazo” method...
Scheme 2: Preparation of diazo reagent 5.
Scheme 3: Scope of NH insertion reaction of N-Boc-α-diazo glutarimide and various N-heterocycles. aIsolated y...
Figure 2: Examples of α-carbonyl NH-heterocycles for which N–H insertion products could not be obtained.
Scheme 4: Examples of N-deprotection of α-modified glutarimides 1.
Scheme 5: Preparation of NH2-containing derivative 10 via reduction of 6n.
Beilstein J. Org. Chem. 2019, 15, 1061–1064, doi:10.3762/bjoc.15.103
Figure 1: Examples of imidazole (1 and 2) and oxazole (3) syntheses from propargylamides previously reported ...
Figure 2: Substrate scope for the three-component synthesis of 5.
Figure 3: Plausible mechanism for the formation of 5.