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A weakly coordinating tert-amide-directed straightforward method was developed for the synthesis of azacoumestans using the corresponding azaheterocycle derivatives and diazonaphthoquinones under cheap Ru(II)-catalyzed conditions. The reaction proceeds via migratory insertion… Click to show full abstract
A weakly coordinating tert-amide-directed straightforward method was developed for the synthesis of azacoumestans using the corresponding azaheterocycle derivatives and diazonaphthoquinones under cheap Ru(II)-catalyzed conditions. The reaction proceeds via migratory insertion of quinoid carbene and subsequent Brønstead acid-mediated cyclization. The optimized C2-selective method offered a wide scope of important azaheterocycles. Bioactive natural products like isolamellarins A and B were synthesized via the developed protocol. Preliminary mechanistic studies highlighted the probable mechanistic pathway.
Journal Title: Organic letters
Year Published: 2022
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