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Paper | Regular issue | Vol 81, No. 10, 2010, pp.2291-2311
Published online, 16th August, 2010
DOI: 10.3987/COM-10-12017
Rearrangement of 2-(2,5-Dioxopyrrolidin-1-yl)guanidine: An Efficient Synthesis and Structure of 3-(5-Amino-1H-1,2,4-triazol-3-yl)propanoic Acid and Derivatives

Victor M. Chernyshev,* Anna V. Chernysheva, and Zoya A. Starikova

*Department of Chemistry, South-Russia State Technical University, Prosveschenya, 132, Novocherkassk 346428, Russia

Abstract

The reaction between aminoguanidine and succinic acid in water under acid catalysis yields a mixture of guanyl- and digyanylhydrazides of succinic acid, which turns into a poorly separable mixture of 3-(5-amino-1H-1,2,4-triazol-3-yl)propanoic acid (3) and 3,3'-(ethane-1,2-diyl)bis(1H-1,2,4-triazol-5-amine) (5) in basic media. The fusion of aminoguanidine hydrochloride with succinic anhydride at 150-170 °C results in the regioselective formation of 2-(2,5-dioxopyrrolidin-1-yl)guanidine hydrochloride (11). Compound 11 upon heating in an aqueous solution in the presence of alkali quantitatively rearranges into 3-(5-amino-1H-1,2,4-triazol-3-yl)propanoic acid (3). This reaction represents a new rearrangement in the 2,5-dioxopyrrolidine series. Investigations by pKa determination, IR, NMR and X-ray revealed that compound 3 exists both in unionized and zwitterionic forms.