Pocar, Donato published the artcileEnamines. XXXI. 4-Nitropyrazoles and 4-nitro-v-triazoles, Safety of 5-Nitro-1H-1,2,3-triazole, the publication is Gazzetta Chimica Italiana (1968), 98(8-9), 949-57, database is CAplus.
2-Morpholino-1-nitroethylene (I) was refluxed 48 hrs. with an equimolar amount p-RC6H4NHN:-CR2Cl (II) (R = H, R1 = Ph) (IIa) in anhydrous CHCl3 with excess Et3N and worked up to give 5% 1,3-diphenyl-4-nitropyrazole, m. 123° (EtOH). Similarly, I reacted with II (R = H, R1 = CO2Et) to give 20% 3-carbethoxy-1-phenyl-4-nitropyrazole, m. 145°, and with II (R = NO2, R1 = CO2Et) to give 6% 3-carbethoxy-4-nitro-1-(4-nitrophenyl)pyrazole, m. 134°. Heating I with PhN3 in a Carius tube 10 hrs. gave 60% 1-phenyl-4-nitro-v-triazole (III), m. 134°. 1-(4-Nitrophenyl)-4-nitro-v-triazole was prepared either by refluxing I with 4-nitrophenyl azide 100 hrs. in EtOH or by nitration of III, m. 201-2°, yields 75 and 80%, resp. Also prepared were 1-phenyl-5-methyl-4-nitro-v-triazole (IV) m. 144°; 1-(4-nitrophenyl)-5-methyl-4-nitro-v-triazole, m. 152°, and 1,5-diphenyl-4-nitro-v-triazole, m. 174-5°. IV was hydrogenated in EtOAc solution at atm. pressure and room temperature over Pd-C to give 90% 4-amino-1-phenyl-5-methyl-v-triazole, m. 103-4° (ligroin), also prepared in a Hofmann degradation from 1-phenyl-5-methyl-4-carboxyl-v-triazole. The same hydrogenation of III gave 4-amino-1-phenyl-v-triazole, m. 104° (H2O). 4-Nitro-v-triazole and 4-methyl-5-nitro-v-triazole were similarly prepared with p-toluenesulfonyl azide (V) 36 hrs., m.161-2 and 177°, resp. 4-Phenyl-5-nitro-v-triazole was prepared by refluxing an EtOH solution of V and α-morpholino-β-nitrostyrene 40 hrs. and working up, m. 197°, as in preparation of III.
Gazzetta Chimica Italiana published new progress about 14544-45-7. 14544-45-7 belongs to triazoles, auxiliary class Triazoles, name is 5-Nitro-1H-1,2,3-triazole, and the molecular formula is C2H2N4O2, Safety of 5-Nitro-1H-1,2,3-triazole.
Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics