Two Sequential Multicomponent Reactions: Synthesis of Thiazolidin-4-yl-1,3,4-oxadiazoles under Mild Conditions

Abstract

This work describes the synthesis of compounds including both thiazolidine and 1,3,4-oxadiazole heterocyclic systems. The preparation is realized following a new synthesis route consisting of two multicomponent reactions. First 3-thiazolines are formed by an Asinger four-component reaction. Conversion of these cyclic imines into α-amino-1,3,4-oxadiazoles is subsequently achieved by a three-component reaction involving (isocyanoimino)triphenyl­phosphorane and a carboxylic acid. The synthesis route is characterized by mild reaction conditions and it tolerates many functional groups. As shown by the conversion into urea derivatives the prepared α-amino-1,3,4-oxadiazoles are marked by their potential in subsequent reactions.

Key words

heterocycles - imines - multicomponent reaction - ring closure - polycycles

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