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Synthetic routes towards tetrazolium and triazolium dinitromethylides

“…5-Amino-1,3-dimethyl-1H-triazole (10) with potassium chloroacetate gave salt 11 (98%) (Scheme 4); structure 11 was supported by CHN elemental analysis, by a singlet at 3.69 ppm for two protons (NCH 2 CO) in the 1 H NMR spectrum, and by the appearance of two new signals at 45.3 (NCH 2 CO) and 168.5 ppm (CO) in the 13 C NMR spectrum. Attempted reactions of this compound with formic acid to provide 3-(dinitromethyl)-4H-1,2,4-triazole (19) failed (Scheme 6). Transamination of 1,1-diamino-2,2-dinitroethene (17) with hydrazine hydrate gave aminohydrazine 18 [3].…”

“…yield 70%, mp 155-156°C) from S-methyl-2thiopseudourea sulfate and methyl hydrazine according to a previously described method [17]. yield 40%, mp 179°C) [19] and 1-(2-oxopropyl)-1,2,4-triazolium-4nitroimide (14) (46%, mp 150-152°C; lit. yield 23%, mp 220-223°C) from 5-aminotetrazole and methyl sulfate as described in [18].…”

Nitroimines: II. Structure of Nitroamino-1,2,4-triazoles

“…The structures were solved by the direct methods and were refined by the full-matrix least-squares procedure in anisotropic approximation (isotropic for hydrogen atoms) using a Data of [9]. b Data of [11].…”

“…According to some authors, compound I is 3-nitroamino-1,2,4-triazole (structure A) [3,[7][8][9], while the others believe that it has the structure of 5-nitroamino-1,2,4-triazole (B) [6,10], or it is referred to as 3(5)-nitroamino-1,2,4-triazole [2,11]. Bonner and Lockhart [12] and Gao et al [13] presumed that the hydrogen atom in molecule I is located at N 4 (structure C).…”

3(5)-Nitroamino-1,2,4-triazole-5(3)-carbohydrazide: Synthesis and Reactions with Aromatic Aldehydes

“…In the 1 H NMR spectra of hydrazones V-IX, protons of the =CH and HNCO groups resonated at δ 8.45-8.80 and 12.30-12.78 ppm, respectively. Hydrazones V-IX characteristically showed in the IR spectra absorption bands due to vibrations of the NH (3455-3360 and 3290-3200 cm -1 ) and C=O groups (1690-1670 cm -1 ); in addition, a number of strong bands belonging to stretching vibrations of the C=N and N-NO 2 groups and bending vibrations of the N-H group were present in the region 1610-1550 cm -1 [10,11]. In the electron spectra of hydrazones V-IX we observed long-wave absorption bands at λ max 296-356 nm (log ε 4.17-4.46); the red shift relative to the corresponding band in the spectrum of initial com- pound IV (λ max 288 nm, log ε 4.10) results from considerable extension of the conjugation chain.…”