10.3987/COM-88-4594
The research investigates the synthesis and reactivity of a series of N-substituted 4-amino-2(5H)-furanones derived from β-tetronic acid. The purpose of the study is to explore the Eschenmoser-Mannich reaction of these furanones, which has not been extensively examined previously, and to understand their potential for α-homologation and use as building blocks for heterocyclic compounds. The researchers synthesized various N-substituted 4-amino-2(5H)-furanones by reacting β-tetronic acid with different aliphatic and aromatic amines. These compounds were then subjected to the Eschenmoser-Mannich reaction, yielding corresponding Mannich bases quantitatively. The study concludes that the 4-amino-2(5H)-furanones exhibit improved reactivity at position 3, as evidenced by their electrophilic substitution reactions and the formation of Mannich bases. The researchers also explored the quaternization of these Mannich bases with methyl iodide, observing the formation of normal and intermolecular quaternary salts, particularly in the case of the 4-anilinofuranone system. The chemicals used in the process include β-tetronic acid, various amines (such as dimethylamine, methylamine, benzylamine, and aniline), Eschenmoser's salt, methyl iodide, and other reagents like potassium carbonate and sodium borohydride for different steps of the synthesis and reactions.