Condensations of Isatin with Acetone by the Knoevenagel
Method1By F. Braude with H. G. LindwallIn a recent article it was shown2 that isatin and acetophenone will condense, in the presence of certain bases, to yield 3-hydroxy-3-phenacyloxindole. This reaction suggested the use of other methyl ketones like acetone. Isatin and acetone condense when present with small amounts of diethylamine to yield 3-acetonyl-3-hydroxyoxindole (I).The condensation involves the /3-carbonyl of the isatin molecule rather than the nitrogen, for N-methylisatin will also react with acetone to yield a product with chemical properties similar to those of (I).Compound (I) decomposes upon the application of heat, or upon being New York, N. Y.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.