Nikolaj V. Latypov

Synthesis and reactions of 5,5-dinitrobarbituric acid

Nitration of barbituric acid at 40°C gave the previously unknown 5,5- dinitrobarbituric acid (3), which readily underwent hydrolysis to dinitroacetylurea (5), which in turn could be hydrolysed in ...

Scalable Synthesis of 1,1-Diamino-2,2-dinitroethene Without Hazardous Intermediates or by-Products

A process for the preparation of 1,1-diamino-2,2-dinitroethene suitable for scale-up was developed. The crucial features to allow scalability and enhance the process safety were the improved synthesis of 2-methoxy-2-methylimidazolidine-4,5-dione and its conversion into 2-hydroxy-2-methylimidazolidine-4,5-dione, which is a new intermediate in the synthesis of 1,1-diamino-2,2-dinitroethene. Its nitration produced 2-(dinitromethylidene)-imidazolidine-4,5-dione, whose hydrolysis into 1,1-diamino-2,2-dinitroethene was further improved. The use of trifluoroacetic acid to remove sulfuric acid prior to hydrolysis is no longer required. The described procedure yields no hazardous intermediates such as dinitromethane or 2-(dinitromethylidene)-5,5-dinitrodihydropyrimidine-4,6(1H,5H)-dione. Thus, the process safety was enhanced in comparison with the commercial production process starting from 2-methylpyrimidine-4,6-dione.

Energetic Plasticizers Based on gem-Dinitrodiols

In this article, the syntheses and attempts at synthesis for the preparation of gem-dinitrodiols and their derivatives are outlined. The three gem-dinitrodiols described are 2,2-dinitropropane-1,3-diol, 3,3-dinitropentane-1,5-diol, and 4,4-dinitroheptane-1,7-diol. The nitrooxy, azido, and azidoacetoxy derivatives of the latter were prepared and are compared to derivatives of the first, which were presented in a previous article. The tedious and expensive synthesis of pentanediol precluded its use as an intermediate. Only one compound both had excellent glass transition temperature and was thermally stable. This compound was 4,4-dinitro-1,7-diazidoheptane.