865879-17-0Relevant academic research and scientific papers
The synthetic versatility of alkoxycarbonyl- and hydroxymethyl-piperazine- 2,5-diones
Chai, Christina L.L.,Elix, John A.,Huleatt, Paul B.
, p. 8722 - 8739 (2007/10/03)
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.
Multi-purpose functionality for the structural elaboration of the piperazine-2,5-dione motif
Chai, Christina L. L.,Elix, John A.,Huleatt, Paul B.
, p. 263 - 265 (2007/10/03)
Mild methods for controlled C- and N-alkylation of 3-benzyloxycarbonylpiperazine-2,5-diones are reported. The benzyloxylcarbonyl substituent can also serve as latent functionality for N-acyliminium ion formation and subsequent trapping enables installation of new carbon and/or heteroatom substituents.
