Aldol condensation with 2,5-diketopiperazines

Abstract

2,5-diketopiperazines (DKPs) are naturally occurring cyclopeptides obtained by the condensation of two amino acids. They are found alone or among other natural products produced by fungi, bacteria, the plant kingdom and mammals

One way of obtaining substituted DKPS is by aldol condensation of 1,4-Diacetylpiperazine-2,5-dione with aldehydes. In this project, we wanted to study the effect of various bases on this reaction for different aldehydes. The best base would be applied to reaction with ketones, which has not been reported.

DBU was found to be to optimal base in reaction with aldehydes, but works poorly for ketones because 1,4-Diacetylpiperazine-2,5-dione is unstable under strongly basic conditions over time.