Photoinduced cyclization of mono- and dianions of N-acyl-o-chloranilines. A general oxindole synthesis

Palladium-Catalyzed Inter- and Intramolecular α-Arylation of Amides. Application of Intramolecular Amide Arylation to the Synthesis of Oxindoles

“…[26][27][28][29][30][31] Metal-catalyzed routes to oxindoles include cyclocarbonylations of 2-aminostyrenes catalyzed by palladium, 32 rhodium catalyzed carbonylations of 2-alkynylanilines, 33 rhodium-and Nafion-H-catalyzed cyclizations of R-diazoamides, 34,35 and intramolecular Heck couplings of 2-haloacryloylanilides. 36,37 Photochemical, 38,39 Ullmantype, 40 and radical 41 promoted cyclizations of saturated 2-haloanilide derivatives have also been reported.…”

“…Friedel−Crafts cyclizations of α-haloacetanilides and variations on the Fischer indole synthesis are the classical methods of oxindole synthesis . Cyclizations of 2-haloacryloylanilide derivatives by a variety of radical initiators have been reported more recently. − Metal-catalyzed routes to oxindoles include cyclocarbonylations of 2-aminostyrenes catalyzed by palladium, rhodium catalyzed carbonylations of 2-alkynylanilines, rhodium- and Nafion-H-catalyzed cyclizations of α-diazoamides, , and intramolecular Heck couplings of 2-haloacryloylanilides. , Photochemical, , Ullman-type, and radical promoted cyclizations of saturated 2-haloanilide derivatives have also been reported.…”

Aza-oxindole synthesis via base promoted Truce–Smiles rearrangement

“…The aza-oxindole structural motif is prevalent in compounds exhibiting interesting biological properties such as oral antiinflammatory activity, and potent TrkA kinase and JAK 3 kinase inhibition. 1 Several synthetic approaches to this moiety have been developed, such as oxidation of aza-indoles, 2 radical cyclisation reactions, 3 Pauson-Khand type [2+2+1] cycloadditions, 4 Pd-catalyzed intramolecular a-pyridynation of amides, 5 photocyclisations, 6 and cyclisation of aminopyridineacetic acids. 7 Recently, we have reported a straightforward and robust protocol for the preparation of aza-oxindoles via CuCl 2 -mediated intramolecular C sp 2 -H/C sp 3 -H coupling.…”

Rh(II)‐Catalyzed Chemoselective Synthesis of 3‐Substituted Oxindoles by C(sp2)−H and C(sp2)−N Functionalization of β‐Enaminoesters

“…[1] Owing to their importance and usefulness, an umber of methods for the constructiono f3 -aryl and 3-alkyloxindoles have been developed. [2] Amongt hese, the general methods for 3-aryloxindoles include palladium-catalyzed intramolecular a-arylation of amides, [3] intramolecular a-arylation of oxindoles with aryl halides, [4] photoinduced cyclization of ahaloacetanilides, [5] and the reactiono fa ryl magnesium chloride to N-substituted isatin followed by Lewis acid-promoted reductive deoxygenation. [6] For the synthesis of 3-alkyloxindoles, the Ru/Bu 4 NI catalyzed intramolecular olefin hydrocarbamoylation of N-(2-vinylphenyl)formamides, [7] Rh-catalyzed domino addition/enolatearylation, [8] and Ru-catalyzed alkylation of oxindole with alcohols [9] have been developed (Scheme1).…”