74066-83-4Relevant academic research and scientific papers
Photocatalytic Synthesis of Polycyclic Indolones
Saget, Tanguy,K?nig, Burkhard
, p. 7004 - 7007 (2020/05/18)
In this work, a photocatalytic strategy for a rapid and modular access to polycyclic indolones starting from readily available indoles is reported. This strategy relies on the use of redox-active esters in combination with an iridium-based photocatalyst under visible-light irradiation. The generation of alkyl radicals through decarboxylative single electron reductions enables intramolecular homolytic aromatic substitutions with a pending indole moiety to afford pyrrolo- and pyridoindolone derivatives under mild conditions. Furthermore, it was demonstrated that these radicals could also be engaged into cascades consisting of an intermolecular Giese-type addition followed by an intramolecular homolytic aromatic substitution to rapidly assemble valuable azepinoindolones.
Oxidative radical cyclization of (ω-iodoalkyl)indoles and pyrroles. Synthesis of (-)-monomorine and three diastereomers
Artis,Cho,Jaime-Figueroa,Muchowski
, p. 2456 - 2466 (2007/10/02)
Addition of excess hydrogen peroxide (10 equiv) to a sonicated solution of FeSO4:7H2O (1 equiv) in DMSO containing the N-(ω-iodoalkyl)indoles 4, 5, 11, and 13 effected oxidative radical cyclization to 6, 7, 14, and 15, respectively. The (ω-iodoalkyl)pyrroles 21, 22, 27, 38, and 49 underwent analogous cyclization reactions to 23, 24, 28, 39, and 50, respectively. The regiochemistry of these radical cyclization reactions was correctly predicted by FMO calculations in all cases but one. For compound 38, FMO calculations indicated that radical attack should take place at both C-3 and C-5. Only the product of cyclization at C-5, i.e., 39, was observed. The enantiomerically pure bicyclic ketone 42, prepared by the above technique from the iodide 53, was converted into 55 which, on catalytic reduction (H2/Rh-Al2O3), gave a mixture of (-)-monomorine (40) and three of its diastereomers 56-58.
