TY - JOUR
T1 - Synthesis and spectroscopic investigation of substituted piperazine-2,5-dione derivatives
AU - Stewart, Craig D.
AU - White, Nicholas G.
AU - Barrow, Russell A.
AU - Reekie, Tristan A.
N1 - Publisher Copyright:
© 2024 The Authors
PY - 2024/3/7
Y1 - 2024/3/7
N2 - The piperazine-2,5-dione moiety is a useful scaffold for functionalisation to generate bioactive molecules. Synthetic methods for accessing substituted piperazine-2,5-diones involve cyclising dipeptides or building from the already established core. Utilising the latter method, we have developed procedures to condense a variety of methoxylated benzaldehydes to exclusively form (Z,Z)-(benzylidene)piperazine-2,5-diones 7. This method can easily be utilised to form both homo- and heterodimeric substituted piperazine-2,5-diones. Subjecting these compounds to hydrogenation affords two isomers. We detail simple NMR analyses that allow for identification of the cis or trans isomers. These analyses, combined with X-ray crystallography have shown that under the hydrogenation conditions used, the cis isomer forms as the major product. The synthetic methods combined with spectral analysis provide a valuable understanding of piperazine-2,5-dione properties.
AB - The piperazine-2,5-dione moiety is a useful scaffold for functionalisation to generate bioactive molecules. Synthetic methods for accessing substituted piperazine-2,5-diones involve cyclising dipeptides or building from the already established core. Utilising the latter method, we have developed procedures to condense a variety of methoxylated benzaldehydes to exclusively form (Z,Z)-(benzylidene)piperazine-2,5-diones 7. This method can easily be utilised to form both homo- and heterodimeric substituted piperazine-2,5-diones. Subjecting these compounds to hydrogenation affords two isomers. We detail simple NMR analyses that allow for identification of the cis or trans isomers. These analyses, combined with X-ray crystallography have shown that under the hydrogenation conditions used, the cis isomer forms as the major product. The synthetic methods combined with spectral analysis provide a valuable understanding of piperazine-2,5-dione properties.
UR - http://www.scopus.com/inward/record.url?scp=85183970748&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2024.133838
DO - 10.1016/j.tet.2024.133838
M3 - Article
SN - 0040-4020
VL - 153
JO - Tetrahedron
JF - Tetrahedron
M1 - 133838
ER -