Synthesis and reactions of 1,1-diamino-2,2-dinitroethylene

Low temperature nitrations of 2-methylimidazole gave in addition to the known 2-methyl-5(4)-nitroimidazole ( 1), 2-(dinitromethylene)-5,5-dinitro-4-imidazolidinone ( 3) and parabanic acid ( 2). The tetranitro compound 3 was also obtained by nitration of 2-methyl-4,5-dihydro-(1H)-5-imidazolone ( 8)....

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Bibliographic Details
Published inTetrahedron Vol. 54; no. 38; pp. 11525 - 11536
Main Authors Latypov, Nikolai V., Bergman, Jan, Langlet, Abraham, Wellmar, Ulf, Bemm, Ulf
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Medicin och hälsovetenskap
Physical Sciences
Science & Technology
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Summary:Low temperature nitrations of 2-methylimidazole gave in addition to the known 2-methyl-5(4)-nitroimidazole ( 1), 2-(dinitromethylene)-5,5-dinitro-4-imidazolidinone ( 3) and parabanic acid ( 2). The tetranitro compound 3 was also obtained by nitration of 2-methyl-4,5-dihydro-(1H)-5-imidazolone ( 8). Thermal decomposition of 3 gave 2-(dinitromethylene)-4,5-imidazolidinedione ( 4) which also was the product from nitration of the new compound 2-methoxy-2-methyl-4,5-imidazolidinedione. Treatment of 4 with aqueous ammonia gave the previously unknown 1,1-diamino-2,2-dinitroethylene ( 5). The physical properties and chemical behaviour of ( 5) are described. Nitration of 2-methylimidazole readily gave 2-(dinitromethylene)-4,5-imidazolidinedione, which could be cleaved under mild conditions yielding 1,1-diamino-2,2-dinitroethylene.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)00673-5