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Paper | Regular issue | Vol 34, No. 7, 1992, pp.1385-1393
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6031
Nitroimidazolones. Synthesis of Deaza Analogues of 3-Nitro-1,2,4-triazol-5-one

John E. Marlin* and Michael O. Killpack

*Frank J. Seiler Research Laboratory, U.S.A.F. Academy, CO 80840, U.S.A.


Analogues of 3-nitro-1,2,4-triazol-5-one (NTO) have been synthesized. The strategy revolves around a new method for the synthesis of imidazolones, namely the addition-elimination reaction of the sodium salt of trimethylsilylethanol with a trimethylsilylethoxymethyl (SEM)-protected dinitroimidazole followed by the acid-catalyzed conversion to the desired nitroimidazole (5). The N-methyl derivatives of 5 were prepared in a similar manner starting from the N-methyldinitroimidazoles.