Hinkel, L. E. published the artcileHydrogen cyanide. X. The tetrapolymer, COA of Formula: C4HN5, the publication is Journal of the Chemical Society (1937), 1432-7, database is CAplus.
cf. C. A. 31, 597.2. The previous evidence for the structure of the polymerized form of HCN is reviewed and further evidence is adduced for its quadrimol. nature. The view that the polymer is diaminomaleic dinitrile is shown to be incorrect and experiments indicate it to be aminoiminosucconitrile (I). The polymerization product of HCN, m. 181° (decomposition), condenses with glyoxal in hot H2O to give 6-hydroxy-2,3-dicyanodihydropyrazine, red, amorphous, decomposes 240° without melting; it is very slowly decomposed by boiling H2O, but H2O containing a little (CO2H)2 gives dicyanopyrazine (II), m. 132°. Hydrolysis of II by Na2O2 in H2O and purification through the Ag salt give pyrazinedicarboxylic acid, m. 193°. The polymer of HCN in Et2O, saturated with dry HCl, gives the HCl salt of I, decomposes 135°. Refluxing the polymer with aldehydes in EtOH for 30 min. gives the following derivatives of I: benzylidene (III), yellow, m. 191° (decomposition); salicylidene, yellow with green tinge, m. 234° (decomposition); m-bromosalicylidene, yellow, m. above 250°; anisylidene, yellow, m. 227° (decomposition); isobutylidene, m. 91° (decomposition); in no case could a 2nd mol. of aldehyde be condensed. The Ac derivative of I m. 164° (decomposition); the di-Ac derivative m. 224° (decomposition); the Ac derivative of III m. 227° (decomposition). Ac2 and I give 2,3-dicyano-5,6-dimethylpyrazine (IV), m. 171°; benzil forms 2,3-dicyano-5,6-diphenylpyrazine, m. 246°. Hydrolysis of IV gives 2,3-dimethylpyrazine-5,6-dicarboxylic acid, m. 200°. The action of HNO2 on I yields 4,5-dicyano-1,2,3-triazole (V), hydrolysis of which gives 1,2,3-triazole-4,5-dicarboxylic acid. The action of HNO2 on the Ac derivative of I forms 4 (or 5)-cyano-1,2,3-triazole-5 (or 4)-carboxamide, m. 219° (decomposition), and V. Oxidation of III gives 4,5-dicyano-2-phenyliminazole, cream, m. 261° (decomposition); hydrolysis gives 2-phenyliminazole-4,5-dicarboxylic acid, m. 243-4°.
Journal of the Chemical Society published new progress about 53817-16-6. 53817-16-6 belongs to triazoles, auxiliary class Triazoles, name is 1H-1,2,3-Triazole-4,5-dicarbonitrile, and the molecular formula is C4HN5, COA of Formula: C4HN5.
Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics