An efficient, one-pot approach has been established for synthesizing a wide range of 3-amino-[1,2,4]-triazolo pyridines and related heterocycles from the electrochemically induced desulfurative cyclization of 2-hydrazinopyridines with isothiocyanates. The protocol allows for the formation of C−N bonds under simple conditions without transition metals or external oxidants. The practicability of this strategy is demonstrated by its broad substrate scope, good functional group compatibility, and gramscale synthesis. The late-stage modification of 3-amino-[1,2,4]triazolo pyridines enables us to obtain several molecules with potent anticancer activity.
An
efficient anodic C(sp3)–H acyloxylation protocol
has been established via intermolecular cross-dehydrogenative C(sp3)–O coupling. The protocol provides various C2-acyloxy
indolin-3-ones without the addition of metal catalysts and external
oxidants because indolin-3-ones can be directly oxidized at the anode.
The effective application of several medical drugs and the realization
of the gram-scale experiment have proven the practicality of this
protocol.
An electrochemical protocol for the construction of substituted isoindolinones via reduction/amidation of 2-carboxybenzaldehydes and amines has been realized. Under metal-free and external-reductant-free electrolytic conditions, the reaction achieves the cascade formation of intermolecular C−N bonds and provides a series of isoindolinones in moderate to good yields. The deuteriumlabeling experiment proves that the hydrogen in the methylene of the product is mainly provided by H 2 O in the system. I soindolinones are an important class of nitrogen-containing structural scaffolds, which appear in a myriad of natural products, biologically active molecules, 1 and clinical drugs, 2 such as TNF-α production inhibitors CC3052 and DWP205190, nonsteroidal anti-inflammatory drug indoprofen, anticancer drug lenalidomide, etc. (Figure 1). For their
An efficient cathodic carbonyl alkylation of aryl ketones
or aldehydes
with unactivated alkyl halides has been realized through the electrochemical
activation of iron. The protocol is believed to include a radical–radical
coupling or nucleophilic addition process, and the formation of ketyl
radicals and alkyl radicals has been demonstrated. The protocol provides
various tertiary or secondary alcohols by the formation of intermolecular
C–C bonds under safe and mild conditions, is scalable, consumes
little energy, and exhibits a broad substrate scope.
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