Syntheses of alkyl (E)-(1-aryl-2-pyrrolidinylidene)acetates

Add time:09/03/2019    Source:sciencedirect.com

Two methods for the synthesis of the title compounds [3] are presented. The first, and less satisfactory, method uses the sulphide contraction, which involves salt formation between alkyl bromoacetates and N-arylpyrrolidine-2-thiones [2] followed by sulphur extrusion. By-products include N-arylpyrrolidin-2-ones [1] and 3-alkoxycarbonylmethylpyrrolidine-2-thiones [5]. A better route is by way of condensation between ethyl 6-chloro-3-oxohexanoate [6] and substituted anilines, followed by intramolecular cyclisation. An unusual Reformatsky reaction with methyl bromoacetate and 1-phenylpyrrolidine-2-thione [2a] is also reported.

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