A convenient method for the synthesis of 2-amino substituted aza-heterocycles from N,N′-disubstituted thioureas using TsCl/NaOH |
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Authors: | Uwe Heinelt Daniela Schultheis Siegfried Jäger Marion Lindenmaier Annett Pollex Henning Sg Beckmann |
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Institution: | Aventis, Chemistry, Building G 878, Industrialpark Höechst, 65926 Frankfurt, Germany |
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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. |
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Keywords: | TsCl/NaOH Heterocycle synthesis Thiourea Ring closure Cyclodesulfurisation |
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