N-Hydroxy amides. Part 6. Synthesis and spectroscopic properties of 1-hydroxypiperazine-2,5-diones
Abstract
1-Hydroxypiperazine-2,5-diones (3a–f) are prepared in good yields, starting with Boc-L-amino acids and N-benzyloxyglycine methyl ester. The rate of cyclisation for N-hydroxy and N-benzyloxydipeptide methyl esters are 38–77 times as large as that of phenylalanylglycine methyl ester. The c.d., 1H n.m.r., i.r., and u.v. spectral data of 1-hydroxypiperazine-2,5-diones are similar to those of the corresponding piperazinediones. A difference is noted in the i.r. carbonyl frequencies in the solid state.