Tautomerism of amidines. IV. Methylation of 4(5)-nitroglyoxaline and 4(5)-phenylglyoxaline was written by Hazeldine, C. E.;Pyman, F. L.;Winchester, John. And the article was included in Chem. Soc. in 1924.Computed Properties of C4H5N3O2 This article mentions the following:
A further study has been made of the influence of various substituents on the relative proportions of the 2 isomeric alkyl derivatives produced by the action of alkyl esters upon amidines. The NO2 group favors the formation of the 5-O2N-1-Me derivative as does the Br derivative but to a smaller extent. The Ph group is exceptional in that the ratio of the 4:1-Me to 5:1-Me derivative is 4.8:1, although its influence is similar to that of the NO2 and Br groups in affecting the results of the distillation of the common methiodides of 4- and 5-substituted 1-methylglyoxalines. 4-Nitro-1-methylglyoxaline (I), m. 133-4°; HCl salt, large prisms, losing HCl at 100°. 5-Nitro derivative (II), m. 55°; HCl salt, small prisms with 2H2O, m. 195° (decomposition); picrate, yellow, m. 153.5°, soluble in about 25 parts boiling H2O. Nitration of 1-methyl-glyoxaline by boiling with HNO3-H2SO4 2 hrs. gave 21% I and 8% II. Methylation of 4(5)-nitroglyoxaline gave 62.3% II and 0.18% I (ratio, 350:1). Reduction of II by SnCl2 and HCl gave NH3, MeNH2 and NH2CH2CO2H. 4-p-Nitrophenyl-1-methylglyoxaline (III), pale yellow, m. 195°; nitrate, cream-colored needles, m. 197° (decomposition); picrate, m. 258°. III is obtained in 56% yield by nitration of 4-phenyl-1-methylglyoxaline, together with about 10% of the nitrate of the o-isomer, decomposes 182°. The 5-p-nitro derivative (IV), lemon-yellow, m. 171-2°; nitrate, m. 213° (decomposition); picrate, m. 184°. Methylation of 4-p-nitrophenylglyoxaline gave a mixture of 28% III and 2.6% IV. Nitration of III gave 90% of the 5-nitro derivative (V), faintly yellow, m. 208-9°; the HCl salt crystallines with 0.5 H2O and loses its HCl at 100°. IV yields the 4-nitro derivative, faintly yellow, m. 187°. Methylation of 5-nitro-4-p-nitrophenylglyoxaline gave 66% of V. Reduction of V with SnCl2 and HCl gave 5-amino-4-p-aminophenyl-1-methylglyoxaline, isolated as the di-HCl salt, needles, darken 200°, do not m. 300°; aqueous solutions give an oil with NaOH which soon darkens in color, or, with NH3, a solution of transient indigo color. It reduces NH4OH-AgNO3 and gives a clear magenta solution with FeCl3. Hydrolysis gave H2NC6H4CH2(NH2)CO2H, NH2Me and NH3. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Computed Properties of C4H5N3O2).
1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Computed Properties of C4H5N3O2
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem