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1 Central European Journal of Energetic Materials

1 2007

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The Study of Some Potential New Synthetic Routes to LLM-105 (2,6-Diamino-3,5-dinitropyrazine 1-oxide)

Bellamy A. J., Golding P.

Central European Journal of Energetic Materials

2007

Vol. 4, nr 3

33-57

The synthesis of LLM-105 (2,6-diamino-3,5-dinitropyrazine 1-oxide) via the direct nitration of 2,6-diaminopyrazine 1-oxide is reported. Two synthetic routes to the starting material 2,6-diaminopyrazine 1-oxide have been investigated. The synthesis of 2,6-diamino-3,5-dinitropyrazine by nitration of 2,6-diaminopyrazine and 2,6-diacetamidopyrazine has also been studied. Whilst mono-nitration of 2,6-diaminopyrazine is very selective, further nitration leads to mixtures of 2,6-diamino-3,5-dinitropyrazine, 6-amino-2-keto-3,5-dinitropyrazine and tetraketopiperazine, the latter predominating in many cases. It was shown that tetraketopiperazine is formed by further reaction of the initially formed 2,6-diamino-3,5-dinitropyrazine. Nitration of 2,6-diacetamidopyrazine does furnish 2,6-diamino-3,5-dinitropyrazine, but the yield is poor.