Cu-Catalyzed Arylation/Acyl Migration Cascade Reaction of Enaminones: Access to N-Fused Polycyclic and 2,3-Disubstituted Indoles

Abstract

An efficient synthesis of N-fused polycyclic and 2,3-disubstituted indoles by copper-catalyzed direct annulation/acyl migration reaction of enaminones is reported. This strategy features cheap and low loading of the catalyst/ligand, readily available starting materials, and good functional group compatibilities. Notably, allyl-containing substrates are also tolerated, which allows the downstream derivatization toward indole alkaloids.

Transacylation in Ferrocenoyl-Purines. NMR and Computational Study of the Isomerization Mechanism

“…The N7 / N9 -transferrocenoylation in purines may be classified as an intramolecular acyl migration, which is of special importance in organic and medicinal chemistry. An acyl shift occurs frequently in carbohydrates, lipids, or peptides − and serves as a reaction channel in prodrug design and various synthetic strategies. − So far, however, only a few studies have coupled experimental and computational methods to clarify the underlying mechanism. In this work, a cluster of earlier relevant examples, including imidazole rings and benzotriazoles, , has been expanded to purines.…”

Recent Advances and Perspectives in the Synthesis and Applications of Tetrahydrocarbazol‐4‐ones†

“…In addition to the Cu-catalyzed/promoted arylation reactions, Pd-catalyzed intramolecular enaminone coupling was also documented and suggested to operate through two types of mechanisms according to the manner of the cyclization, namely, Heck reaction and α-arylation. [32,33] A detailed mechanistic investigation of such type of reactions was carried out by Nolan group both Scheme 16 CuI-promoted cyclization of N-2-haloaryl-substituted enaminones and synthesis of (+)-aspidospermidine…”

Photo-Fries-type rearrangement of cyclic enamides. An efficient route to structurally diverse five-membered enaminones

“…Five-membered enaminones are widely used as attractive building blocks for the synthesis of structurally diverse heterocycles. 11–24 For example, Liu et al reported the synthesis of N -fused polycyclic and 2,3-disubstituted indoles by the copper-catalyzed direct annulation/acyl migration reaction of cyclic enaminones. 11 In turn, Troin and coworkers showed an efficient route to indole alkaloid synthons via the photochemical cyclization of aryl enaminones.…”