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The synthesis and structure of 1,2,3,4-tetrahydro-2,4,4-trimethyl-8-nitroimidazo[1,5-d] [1,2,4]triazin-1-one, C8H11N5O3: A heterocycle with a rare ring system

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Abstract

The title compound (IV) was isolated as a by-product during the course of purification of 4-nitroimidazol-5-(N′-methyl)hydrazide (II) by silica gel flash chromatography, employing chloroform-acetone (4:1) as the eluting solvent. The crystals are monoclinic, space groupP21/c,a=7.425(1),b=13.615(2),c=10.359(2) Å,β=97.66(1)°,d caled=1.44 g cm−3,μ (Mo)=1.06 mm−1,T=298 K. The number of unique reflections=2401, reflections withI≥3 σ(I)=1773;R=0.051,R w =0.061. The bond distances inIV are: N-N, 1.419(3); N-C(=0), 1.359(3); N(H)-C(CH3), 1.457(3); N(C)-C(CH3), 1.501(3); N=C, 1.316(3); C=C, 1.368(3), N-C(=N), 1.353(3); N-C(=C), 1.367(2) Å.

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Hosmane, R.S., Lim, B.B., Siriwardane, U. et al. The synthesis and structure of 1,2,3,4-tetrahydro-2,4,4-trimethyl-8-nitroimidazo[1,5-d] [1,2,4]triazin-1-one, C8H11N5O3: A heterocycle with a rare ring system. Journal of Crystallographic and Spectroscopic Research 21, 353–356 (1991). https://doi.org/10.1007/BF01156088

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Keywords

  • Methyl
  • Reflection
  • Chromatography
  • Physical Chemistry
  • Purification