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Cyclisierungsreaktionen β, γ-ungesättigter Kohlensäurederivate. IV [1]. Synthese von N-substituierten Thiazolidin-2-onen und 2-Alkoxy-2-thiazolinen aus β,γ-ungesättigten Thiocarbamidsäureestern

✍ Scribed by Prof. Dr. M. Mühlstädt; Dr. R. Widera


Publisher
John Wiley and Sons
Year
1981
Tongue
English
Weight
460 KB
Volume
323
Category
Article
ISSN
1615-4150

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✦ Synopsis


Cyclization Reactions of β,γ‐Unsaturated Derivatives of Carbonic Acid. IV. Synthesis of N‐Substituted Thiazolidine‐2‐ones and 2‐Alkoxy‐2‐thiazolines from β,γ‐Unsaturated Thiocarbamic Acid Esters

The reaction between N‐substituted β,γ‐unsaturated thiourethans and dry hydrogen chloride or bromine occurs in methylene chloride at room temperature. The thiourethans 1 a–4 a react with hydrogen chloride to give mixtures of corresponding 2‐alkoxy‐2‐thiazolines 6–9 and the thiazolidine‐2‐one 11 a. A useful synthetic route to N‐substituted thiazolidine‐2‐ones 11 is demonstrated by the reaction of N,N‐disubstituted β,γ‐unsaturated thiourethans with hydrogen chloride and bromine. The i.r. and H‐n.m.r.‐data of the compounds are described.


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