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One-step diketopiperazine synthesis using phase transfer catalysis

2009-04-15, O'Reilly, Elaine, Lestini, Elena, Balducci, Daniele, Paradisi, Francesca

A simple and efficient one-step procedure is described for the synthesis of a number of symmetrical 1,4-disubstituted piperazine-2,5-diones under phase transfer conditions. The reactions are carried out at room temperature, starting from a suitable N-chloroacetamide in the presence of an aqueous solution of sodium hydroxide. Piperazine-2,5-diones were obtained with excellent selectivity in yields of up to 90%.

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From amines to diketopiperazines: a one-pot approach

2010-03-31, O'Reilly, Elaine, Pes, Lara, Paradisi, Francesca

An efficient one-pot synthesis is described for the preparation of 1,4-disubstituted piperazine-2,5-diones starting from a suitable amine and chloroacetyl chloride in the presence of an aqueous base. The resulting chloroacetamide is cyclised in situ by employing the phase-transfer (PT) catalyst, benzyltriethylammonium chloride (TEBA). The products are isolated in excellent yields of up to 90%.