ChemInform Abstract: Synthesis of 3‐Mercapto‐2(5H)‐furanones via Reaction of Dilithio‐2,4‐ thiazolidinedione with α‐Halo Ketones.

Abstract

Synthesis of 3-Mercapto-2(5H)-furanones via Reaction of Dilithio-2,4-thiazolidinedione with α-Halo Ketones.-Dilithio-2,4thiazolidinedione generated by treatment of 2,4-thiazolidinedione (I) with n-butyllithium undergoes reaction with the . alpha.-halo ketones (II) to yield the allylic alcohols (III) and (IV). These products are further transformed into alkylated allylic alcohols such as (IIIf) or 5-hydroxy-2-mercaptofuranones such as (VIII). ( Mechanism). -(ZASK, A.; NOWICKI, J. W.; JIRKOVSKY, I.; VAN ENGEN, D.; Tetrahedron Lett. 34 (1993) 17, 2719-2722; Dep. Med.