Abstract
When crystallized from ethanol, 7,7-dimethyl-2-pyridin-4-yl-6,7-dihydro-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine forms crystals which have monoclinic (P21/n) symmetry with unit cell dimensions a = 7.3326(5) Å, b = 19.4897(14) Å, c = 8.6586(6) Å, α = 90°, β = 106.069(2)°, γ = 90°, V = 1189.06(14) Å3, Z = 4. The triazine ring in the molecule has a flattened boat conformation with gem-dimethyl groups as flagpole and bowsprit at the bow. The puckering parameters for the ring are: Q = 0.2996(14) Å, θ = 111.7(3)° and φ = 124.1(3)°. In the crystal, molecules are arranged in the three types of chains generated by the intermolecular NH···N hydrogen bonds. The extended chains with the C(11) graph-set motif running along a [010] axis are formed by the amino group hydrogen atom and the pyridine nitrogen atom of another molecule. The C(4)C(6) chains with the R22(8) binary graph-set motif running along a [101] direction are formed by linking the amino group hydrogen atom and the hydrogen atom at the triazine nitrogen atom with the triazole and triazine nitrogen atoms of another molecule, respectively. The centrosymmetric inverted dimers are formed via the C-H···π interactions between the methyl group hydrogen and the pyridine ring of the pair molecule.
Highlights
Compounds with 1,2,4-triazolo[1,5-a]triazine ring system have not been found in nature
The chemistry and biological activity of 1,2,4-triazolo[1,5-a]triazines have been extensively explored and this heterocyclic system has been well recognized as a promising scaffold for the construction of molecules with diverse biological effects [2]
In our search for potential therapeutic agents in this class of compounds we developed a number of effective synthetic procedures for 1,2,4-triazolo[1,5-a]triazines [3,4,5,6,7] with particular interest to the heterocyclizations of 1,2,4-triazol-3(5)-yl guanidines [4,5,6,7]
Summary
Compounds with 1,2,4-triazolo[1,5-a]triazine ring system have not been found in nature. This heterocyclic system resembles purine which is one of the most important heterocycles in nature. In our search for potential therapeutic agents in this class of compounds we developed a number of effective synthetic procedures for 1,2,4-triazolo[1,5-a]triazines [3,4,5,6,7] with particular interest to the heterocyclizations of 1,2,4-triazol-3(5)-yl guanidines [4,5,6,7]. In continuation of our research program on the synthesis and structural analysis of potentially bioactive 1,2,4-triazolo[1,5-a]triazines, we synthesized 7,7-dimethyl-2-pyridin-4-yl-6,7-dihydro-1,2,4triazolo[1,5-a][1,3,5]triazin-5-amine (1) according to the previously reported general procedure [6,7]. The molecule 1 shares gem-dimethyl substituted dihydro-1,3,5-triazin-5-amine structure moiety with the antifolate drug cycloguanil and its fused analogues 2 (Figure 1) inhibiting dihydrofolate reductase [14,15,16]
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