The objective of this investigation was to develop a new synthetic method for the asymmetric synthesis of imidazolinones. This method involved an addition-cyclization reaction of an optically pure alpha-amino acid ester and a nitrile. While imidazolinones have been synthesized by other means, this synthetic route has the advantage of producing an enantiomerically pure heterocycle. Furthermore, the wide variety of amino acids and nitriles available could produce an extensive series of imidazolinone derivatives whose potential for therapeutic uses could be explored. The first step in this reaction involved the amino addition of an a-amino acid ester to a nitrile to give an intermediate amidine ester. This intermediate could then undergo intramolecular ring closure to form the imidazolinone via the amidinium ion or the amidine. This investigation found base catalysis, aluminum chloride catalysis, Bronsted-acid catalysis and mercury(ll) catalysis to be unsuccessful in effecting amino additions to aliphatic and aromatic nitriles under the given conditions. However, amino addition to trichloroacetonitrile was successful, but only resulted in the formation of the amidine rather than spontaneously ring-closing to form the imidazolinone.
Library of Congress Subject Headings
Imidazolines; Esters; Nitriles; Organic compounds--Synthesis
Department, Program, or Center
School of Chemistry and Materials Science (COS)
Del Vecchio, Franklin A., "An Investigation into the asymmetric synthesis of imidazolinones via reaction of chiral alpha-amino acid esters with nitrils" (1991). Thesis. Rochester Institute of Technology. Accessed from
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