ChemInform Abstract: THE CHEMISTRY OF ISATIN

Abstract

Publisher Summary This chapter reviews developments in the field of isatin from 1944 to late 1974. The most frequently used synthesis of isatins is the Sandmeyer procedure, which involves the formation of an isonitrosoacetanilide from an aniline, chloral hydrate, and hydroxylamine. The isonitrosoacetanilide is converted into the isatin on treatment with sulfuric acid, or less frequently polyphosphoric. The Sandmeyer method has been used with di- and trisubstituted aniline to prepare di- and tri-substituted isatins. Isatin sodium or potassium salts react with dimethyl and dieth sulfate, a variety of alkyl halides, acyl halides, and anhydrides to give N-alkyl and N-acylisatins. N-substitutcd isatins have also been prepared by reactions of some of the compounds that were described earlier. A number of reactions that do not reasonably fit in other categories are included in this chapter. A number of complexes of isatin and metal salts have been reported. Extensive studies have been reported on infrared vibrational frequency correlations of isatin and a variety of substituted isatin. A number of studies of the ultraviolet absorption spectra of isatins have appeared. The most frequently reported oxidation reaction of isatins is the oxidation with alkaline hydrogen peroxide to give anthranilic acids. This procedure has been both as a proof of structure of isatins and as a method of synthesis of anthranilic acids. A wide variety of substituted isatins has reacted with hydroxylamine to give isatin-3-oximes. The cyclizations of certain 2-substituted isatin derivatives were studied so as to compare them with the above cyclizations. The chapter closes with a discussion on polymers.