1093258-27-5Relevant academic research and scientific papers
Efficient, one-pot transformation of indoles into functionalized oxindole and spirooxindole systems under Swern conditions
López-Alvarado, Pilar,Steinhoff, Judith,Miranda, Sonia,Avenda?o, Carmen,Carlos Menéndez
experimental part, p. 1660 - 1672 (2009/05/09)
The reaction of indole derivatives bearing a 3- or 4-hydroxyalkyl chain with dimethylsulfoxide and oxalyl chloride under Swern conditions led to a one-pot, three-component process involving three different synthetic transformations, namely oxidation of indole to oxindole, introduction of a chlorine substituent at the oxindole C-3 position and substitution of the hydroxyl group in the side chain by chlorine, in good to excellent overall yields. The same conditions, applied to a 2-methylindole, afforded a 2-formylindole derivative oxidized at its side chain. The reaction starting from one indole with a 2-hydroxyalkyl chain furnished 3-(2-hydroxyalkyl)oxindoles. Finally, application of the Swern conditions to derivatives of indole-3-propionic or -butyric acid afforded 3-spirooxindole lactones.
