Efficient synthesis of 5-(2-hydroxyethyl)-2-phenylimino- 1,3-thiazolidin-4-ones and 5-(2-hydroxyethyl)-2-phenylamino-4,5-dihydro-1,3-thiazol-4-ones

✍ Scribed by Jiří Váňa; Jiří Hanusek; Aleš Růžička; Miloš Sedlák

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2009
• Tongue: English
• Weight: 159 KB
• Volume: 46
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.118

✦ Synopsis

Abstract

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A new method for the synthesis of substituted 5‐(2‐hydroxyethyl)‐2‐phenylimino‐1,3‐thiazolidin‐4‐ones and 5‐(2‐hydroxyethyl)‐2‐phenylamino‐4,5‐dihydro‐1,3‐thiazol‐4‐ones is described, starting from phenylthioureas and 3‐bromotetrahydrofuran‐2‐one. The reaction proceeds under mild conditions, is very simple to perform, and is applicable to a relatively wide range of substituents in benzene nucleus. Some 1,3‐thiazolidin‐4‐ones show dynamic NMR behavior in solution because of prototropy tautomerism and E‐/Z‐stereoisomerism. J. Heterocyclic Chem., (2009).