The synthetic versatility of alkoxycarbonyl- and hydroxymethyl-piperazine-2,5-diones |
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Authors: | Christina L.L. Chai John A. Elix Paul B. Huleatt |
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Affiliation: | Department of Chemistry, The Faculties, Australian National University, Canberra, ACT 0200, Australia |
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Abstract: | Alkoxycarbonylpiperazine-2,5-diones are versatile precursors for the α-functionalisation of piperazine-2,5-diones. The alkoxycarbonyl group activates the α-carbon position to alkylation reactions and this provides a mild and selective method for the extension of the carbon framework of piperazine-2,5-diones. In addition, the alkoxycarbonyl group can be converted to the carboxy group, which in turn can be ‘deleted’ or manipulated for the installation of carbon and/or heteroatom substituents where desired, the latter via N-acyliminium chemistry. We also demonstrate that hydroxymethylpiperazine-2,5-diones complement carboxypiperazinediones as precursors for the generation of N-acyliminium ions. |
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Keywords: | N-Acyliminium ions Alkylations Amino acids and derivatives Trapping reactions |
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