ChemInform Abstract: MANNICH‐REAKTION VON THIAZOLIDINONEN‐(4) UND CYCLISCHEN AMINEN

Abstract

Die Umsetzung von 2‐Imino‐3‐aryl‐4‐oxo‐thiazolidinen (I) mit Formaldehyd (II) und den cyclischen Aminen (III) führt zu den Mannich‐Basen (IV) bzw. (VI).

Chemistry and biological activity of thiazolidinones

“…Svetkin et al 209 further reported the Mannich reaction of 2-imino-3-aryl-4-thiazolidinones with secondary amines and formaldehyde, giving products of type 199 and 200. l,2-Bis(2-phenyl-4-oxothiazolidin-3-yl)ethane obtained by the reaction of dibenzal ethylenediamine with thioglycolic acid in dry benzene is oxidized to dioxides 201 by heating in AcOH and 33% hydrogen peroxide. 117 However, 4-thiazolidinones on treatment with 30% H202 in a mixture of cold acetic acid and acetic anhydride give the 4-thiazolidinone S-monooxide deriva-tives210 (202).…”

Progress in the chemistry of 4‐ thiazolidinones

“…The imino nitrogen appears also to be a very efficient nucleophilic center [37]. Despite the fact that 2-iminothiazolidin-4-one (3) has four nucleophilic reaction centers, viz., the two nitrogens (imino and amido), oxygen and C 5 atoms, its aminomethylation usually takes place only at the ring nitrogen atom [38,39] or, if it is substituted, at the exocylic nitrogen atom [40,41].…”