Advertisement

Chemistry of Heterocyclic Compounds

, Volume 46, Issue 5, pp 627–628 | Cite as

Recyclization of 2-(2,5-dioxopyrrolidin-1-yl)-guanidine under the action of aliphatic amines. a novel method for the synthesis of 3-(5-amino-1h-1,2,4-triazol-3-yl)propanoic acid amides

  • V. M. Chernyshev
  • A. V. Chernysheva
Article

We have previously reported [1] that 2-(2,5-dioxopyrrolidin-1-yl)guanidine hydrochloride (1), prepared by fusion of the aminoguanidine hydrochloride (2) with succinic anhydride, rearranges to 3-(5-amino-1H-1,2,4-triazol-3-yl)propanoic acid when heated in aqueous alkali solution.

In this work we have shown the action of weak bases on compound 1 gives the free 2-(2,5-di-oxopyrrolidin-1-yl)guanidine ( 3). When heated with aliphatic amines in DMF compound 3 undergoes recyclization to give the 3-(5-amino-1H-1,2,4-triazol-3-yl)propanoic acid amides 4a-e in high yield. The mechanism proposed includes a nucleophilic attack of the amine at the carbonyl group, opening of the pyrrolidin-2,5-dione fragment to form the guanylhydrazide A, and its subsequent cyclization to triazole 4.

Keywords

amides amines 3-(5-amino-1H-1,2,4-triazol-3-yl)propanoic acid 2-(2,5-dioxopyrrolidin-1-yl)- guanidine recyclization 

Reference

  1. 1.
    A. V. Chernysheva, Diss. Cand. Chem. Sci., Ivanovo (2009).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2010

Authors and Affiliations

  1. 1.South-Russian State Technical UniversityNovocherkasskRussia

Personalised recommendations