Antiinflammatory oxindolecarboxanilides

Abstract

Two procedures for preparing 3-oxindolecarboxanilides are described. 2',4'-Difluorocarboxanilides of this series have potent antiinflammatory activity in the carrageenan-induced rat foot edema test. Physiochemical properties are reported and discussed in terms of relationship to antiinflammatory activity (rats) and plasma half-life (dogs).

A Fluorous, Pummerer Cyclative‐Capture Strategy for the Synthesis of N‐Heterocycles

“…5-Fluoro-1-methyl-1,3-dihydroindol-2-one: [32] General procedure C was followed. Thus, treatment of 5-fluoro-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-methyl-1,3-dihydroindol-2-one (8) (170 mg, 0.26 mmol, 1 equiv) in THF (3 mL) with SmI 2 (6.5 mL of a 0.1 m solution in THF, 0.65 mmol, 2.5 equiv) and purification by fluorous chromatography gave the title compound (31 mg, 0.19 mmol, 71 %) as an orange oil.…”

Kinetics and Mechanism of Oxidative Conversion of 5-Hydroxyindole to 2-Oxo-5-hydroxyindole by Chloramine-B in Basic Solutions

“…In the present kinetic study, 5-hydroxyindole is oxidized to 2-oxo-5-hydroxyindole, which is biologically and pharmaceutically important. It is also a precursor in the synthesis of natural products [10].…”

Highly Enantioselective Michael Addition of 2‐Oxindole‐ 3‐carboxylate Esters to Nitroolefins Promoted by Cinchona Alkaloid‐Thiourea‐Brønsted Acid Cocatalysts

“…[10] However, to the best of our knowledge, ethyl 2-oxoindoline-3-carboxylate (easily derived from oxindole) [11] has been less used as a nucleophile in the organocatalysis field. [10] However, to the best of our knowledge, ethyl 2-oxoindoline-3-carboxylate (easily derived from oxindole) [11] has been less used as a nucleophile in the organocatalysis field.…”

“…Unfortunately, the level of stereocontrol decreased obviously (entries [11][12][13][14]. Unfortunately, the level of stereocontrol decreased obviously (entries [11][12][13][14].…”