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

Sergey V. Sysolyatin; Artyom E. Paromov

doi:10.3762/bxiv.2019.105.v1

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

Sergey V. Sysolyatin and
Artyom E. Paromov

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. https://doi.org/10.3762/bxiv.2019.105.v1

Published 16 Sep 2019

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SUBJECT AREAS

Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

Abstract

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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© 2019 Sysolyatin and Paromov; licensee Beilstein-Institut.
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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)