4‐Thiazolidinones and 2,4‐thiazolidinediones from α‐mercaptopropionic acid and carbodiimides

Abstract

2,3‐Substituted 5‐methyl‐4‐thiazolidinones (1) and 3‐substituted 5‐methyl‐2,4‐thiazolidine‐diones (II) were prepared by reacting some carbodiimides with α‐mercaptopropionic acid, with the purpose of obtaining potentially chemotherapeutic agents. It is noteworthy that 3‐cyclohexyl‐5‐methyl‐2,4‐thiazolidinedione (IId) was obtained in three different crystalline structures. Some secondary compounds were also obtained: the N,N‐disubstituted ureas (III) and thioureas (IV) in all cases, the dianilides (V) and the tri‐substituted guanidines (VI) from the arylcarbodiimides, and the dithiolactide (VII) from the isopropyl‐ and cyclohexylcarbodiimides.

Chemistry and biological activity of thiazolidinones

“…The imino-amino tautomerism of 2-imino-4-thiazolidinones and its derivatives was studied by infrared nc6h5 ArHC A and 4-thiazolidinones have been reported by other workers (ref 105,110,119,123,134,[149][150][151]164,176,179,184,225,258,259,[264][265][266][267].…”

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

“…Another portion of the product was recovered from the filtrate to give 3c (4.30 g) (total: 14.6 g, 45.6%), mp 140–142°C, lit . 142°C , 140°C . This synthesis method is suitable for the synthesis of compounds 3c , 3e , 3f , 3g , 3h , and 3j (Scheme ).…”

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

“…122 was added to disubstituted methanediimine 121 a – d to form corresponding 5‐methyl‐2,3‐disubstituted‐2‐imino4‐thiazolidineone 123 a – d which is further converted to 5‐methyl‐3‐substituted‐2,4‐thiazolidinedione 124 a – d (Scheme 36). [115] …”