An Environment-friendly Synthesis of 2,3-Disubstituted-2-iminothiazoline-4-ones

A series of 2,3-substituted-2-iminothiazoline-4-ones derivatives have been synthesized via an improved method including an auto-catalyzed reaction. This method avoided using any extra catalyst except for the reaction material. This method has been successful in both the aromatic substituted 2-iminothiazolines and the alkyl substituted 2-iminothiazolines. The special product with a hydroxyl group on the 2-iminogroup of 1,3-thiazoline-4-ones has also been obtained unexpectedly. The possible mechanism has been proposed for the special process of dealkylation and hydroxylation. This method offered a special way to afford the 2-hydroxyimino-substituted thiazoline-4-one derivatives in an efficient and eco-friendly way. The mechanism of the transformation under acid condition has also been proposed.