170376-79-1Relevant academic research and scientific papers
Directing Bromination of Piperazine-2,5-diones
Badran, Terry W.,Chai, Christina L. L.,Easton, Christopher J.,Harper, Jason B.,Page, Dennis M.
, p. 1379 - 1384 (1995)
From intermolecular and intramolecular competition experiments, it has been established that, by comparison with an N-methyl substituent, an N-acetyl group deactivates glycine residues in piperazine-2,5-diones towards free-radical bromination.Combined with the ease of introduction and removal of N-acetyl substituents, the deactivating effect provides a method for regiocontrolled functionalization of these compounds.
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.
