Synthesis of Functional 2‐Substituted 1,3‐Dinitroimidazolidines,Propellants, Explosives, Pyrotechnics

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Synthesis of Functional 2‐Substituted 1,3‐Dinitroimidazolidines
Propellants, Explosives, Pyrotechnics ( IF 1.7 ) Pub Date : 2020-05-14 , DOI: 10.1002/prep.202000017
Sergey V. Sysolyatin ₁ , Artyom E. Paromov ₁

Affiliation

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‐dinitroimidazolidine‐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.

中文翻译：

合成功能性2取代的1,3-二硝基咪唑烷

本文合成了三个新的功能性2-取代的1,3-二硝基咪唑烷。建议通过乙醛酸乙酯与胺或酰胺衍生物的缩合反应合成结构上不同的α，α-二氨基氨基羧酸的合成策略。研究了1,3-二硝基咪唑烷-2-羧酸乙酯的碱和酸催化水解。分离出一系列水解产物。进行了1,3-二硝基咪唑烷-2-羧酸的Curtius重排成2-异氰酸基-1,3-二硝基咪唑烷的过程。研究了1,3-二硝基咪唑烷-2-羰基叠氮化物和2-异氰酸基-1,3-二硝基咪唑烷的水解过程。1,3-二硝基咪唑烷-2-胺被捕获为1,3-双（1,3-二硝基咪唑啉-2--2-基）脲。

更新日期：2020-05-14

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