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A convenient method for the synthesis of 2-amino substituted aza-heterocycles from N,N′-disubstituted thioureas using TsCl/NaOH
Authors:Uwe Heinelt  Daniela Schultheis  Siegfried Jäger  Marion Lindenmaier  Annett Pollex  Henning Sg Beckmann
Institution:Aventis, Chemistry, Building G 878, Industrialpark Höechst, 65926 Frankfurt, Germany
Abstract:p-Toluenesulfonyl chloride (TsCl)/NaOH has been introduced as reagent combination for the synthesis of 2-amino-oxa- or 2-amino-thiazolidines from N-(2-hydroxyethyl)-thioureas, but its general application in heterocycle synthesis has not been investigated. In this paper the convenient and efficient synthesis of a variety of 2-amino-substituted 1-aza 3-(aza, oxo or thio) heterocycles of different substitution and ring sizes is described. The application of polymer-supported TsCl facilitates work-up and renders the reaction conditions very suitable for parallel or robot synthesis.
Keywords:TsCl/NaOH  Heterocycle synthesis  Thiourea  Ring closure  Cyclodesulfurisation
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