Synthesis of functional 2-substituted 1,3-dinitroimidazolidines. A new synthetic approach to high-energy compounds

  1. Sergey V. Sysolyatin and
  2. Artyom E. ParomovORCID Logo

Submitting author affiliation: Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), Biysk, Russian Federation

Beilstein Arch. 2019, 2019105.

Published 16 Sep 2019

  • Preprint


Three new functional 2-substituted 1,3-dinitroImidazolidines  were synthesized herein. A synthetic strategy is suggested for structurally different α,α-dinitraminocarboxylic acids via condensation of glyoxylic acid ethyl ester with amine or amide derivatives. Alkali- and acid-catalyzed hydrolyses of ethyl 1,3-dinitro-1,3-diazacyclopentane-2-carboxylate were studied. A series of hydrolysis products were isolated. The Curtius rearrangement of 1,3-dinitroimidazolidine-2-carboxylic acid to 2-isocyanato-1,3-dinitroimidazolidine was carried out. Hydrolyses of 1,3-dinitroimidazolidine-2-carbonyl azide and 2-isocyanato-1,3-dinitroimidazolidine were studied. 1,3-Dinitroimidazolidine-2-amine was captured as 1,3-bis(1,3-dinitroimidazolidin-2-yl)urea.

Keywords: 2-substituted 1,3-dinitroImidazolidines, isocyanate, hydrolysis, Curtius rearrangement

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Sysolyatin, S. V.; Paromov, A. E. Beilstein Arch. 2019, 2019105. doi:10.3762/bxiv.2019.105.v1

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