Synthesis and characterization of chiral imidazolinones

The commercial application of imidazolinone derivatives can be found in herbicides where they inhibit acetolactate synthase (ALS; EC 4.1.3.18; also known as acetohydroxyacid synthase). The imidazolinone class of herbicides have the advantage of long term activity and low mammalian toxicity. Another application of imidazolinone derivatives is in the preparation of a-alkyl-amino acids. The objective of this investigation was to explore the asymmetric synthesis of imidazolinones through the condensation of a variety of imidate ethyl esters and ccamino acids. Furthermore, it was of interest to characterize the chiral properties of a series of imidazolinone derivatives for future investigation. In this research project, the method of synthesis of imidazolinones was applied and modified from the method which was established in the work of Kidwai, A. Q. and Devasia. G. M. in 1962. (J. Org. Chem. 1962, 27, 4527) Their synthetic work was only successful with aromatic amino acids and benzimidates, therefore, an attempt was made to generalize the preparation of imidazolinones to include nonaromatic systems in this study