An Unusual Oxidation of a Benzylic Methylene Group by Thionyl Chloride: A Synthesis of 1,3-Dihydro-2-[2-(dimethylamino)ethyl]-1,3-dioxopyrrolo[3,4-c]acridine Derivatives

Preparation and X-ray Structural Study of 1-Arylbenziodoxolones

“…It was previously established that the reactions of 1-phenylbenziodoxolone 2a with nucleophiles (e.g., amines) proceed exclusively in the benziodoxolone ring with substitution of PhI and formation of the respective o -substituted benzoic acids . This reactivity pattern is in agreement with general regioselectivity of the reactions of nonsymmetrical iodonium salts with nucleophiles, in which substitution occurs predominantly in the more electron-deficient aromatic ring .…”

“…1-Phenyl-1,2-benziodoxole-3­(1 H )-one 2a , commonly known under the names of 1-phenylbenziodoxolone or diphenyliodonium-2-carboxylate, is the most important representative of arylbenziodoxoles. 1-Phenylbenziodoxolone 2a is a classical reagent that is commonly used for the generation of benzyne under heating or UV irradiation. , It has also found synthetic application for the preparation of o -substituted benzoic acids, which serve as important intermediate products in the synthesis of various biologically active compounds . Phenylbenziodoxolone 2a is commercially available or can be prepared by the oxidation of 2-iodobenzoic acid 1 with potassium persulfate followed by addition of benzene according to the procedure published in Organic Syntheses (Scheme ) .…”

Highly Chemoselective One‐Step Synthesis of Novel N‐Substituted‐Pyrrolo[3,4‐b]quinoline‐1,3‐diones via Palladium‐Catalyzed Aminocarbonylation/Carbonylative Cyclisation Sequence

“…Howbeit, tremendous synthetic procedures have been reported for N ‐substituted‐pyrroloquinolinediones. In this regard, sequential reactions based on Dieckman condensation, [18] oxidative annulation followed by dehydrogenation and N ‐demethylation, [19] oxidation in pyrroloacridone series, [20] and multicomponent aza‐photocyclization reaction [21] are the notable examples. Peculiarly, pyrrolo[3,4‐b]quinoline‐1,3‐diones ( VIII ), a very relevant subfamily of pyrrolodione‐annulated quinolines, are prepared through common methods reported as multistep synthesis, and usually involving quinoline‐based substrates ( IX–XII ) (Scheme 1).…”

Selective C═O Reduction in Phthalimide with Nickel(0) Compounds

“…However, the specific use of phthalimide for the preparation of isoindolinone is given in just a handful of reports; the first was a catalytic synthesis using activated nickel at 200 °C and high pressure of H 2 (200–250 atm), to give isoindolinone in 80% yield . The second procedure used phthalimide in glacial acetic acid with Zn dust under reflux, the third method involved the reaction of phthalimide under similarly harsh conditions with HOAc, HCl, and Sn to give the product in 47% yield, and the most recent report by Dixneuf and co-workers used a series of Ru-based catalysts which are efficient precursors for the monoreduction of cyclic imides in water under relatively mild H 2 pressure (60 bar) at 90 °C; of note, with this method octahydroisoindolinone is obtained in 80% yield. A recent report shows a different reactivity for imides involved in a nickel-catalyzed cross coupling of phthalimides in the presence of diorganozinc reagents via a decarbonylative process to produce ortho-substituted benzamides in high yields (>70%) …”