Bilton, J. A. published the artcilePhthalocyanines. X. Experiments in the pyrrole, isoöxazole, pyridazine, furan and triazole series, Category: triazoles, the publication is Journal of the Chemical Society (1937), 922-9, database is CAplus.
The general result of this series was that no phthaloeyanine-like pigment was obtained in any of the 5 series investigated. In some cases this appears to be a genuine neg. and in agreement with theory; in others the result is inconclusive, as suitably close intermediates could not be prepared Di-Et 2,5.-dimethylpyrrole-3,4-dicarboxylic acid does not react with NH3 to form the diamide; it also could not be prepared through the acid chloride. The Na compound of NCCH2Ac did not react with I or α-bromocyanoacetone (from NCCH2Ac and Br, b12 43° to give diacetylsuccinonitrile, neither could the pyrrole be obtained by direct condensation of these compounds with NH3. Me 1,2-diacetylsuccinate, b20, 120°, m. 113.5°; aqueous NH4OH gave only a brown oil. Et 3-formyl-2,5-dimethylpyrrole-4-carboxylate and its oxime were prepared from Et 2,5-dimethylpyrrole-3-carboxylate; dehydration of the oxime yields Et 3-cyano-2,5-dimethylpyrrole-4-carboxylate, m. 152°, which does not yield an amide on heating under pressure with NH3-MeOH or aqueous NH4OH. Hydrolysis gives the free acid, m. 288°(decomposition), which, on heating at 200° and 13 mm., gives 73% of 3-cyano-2,5-dimethylpyrrole, m. 89°. Through the imine-HCl this was converted into the 4-formyl derivative, yellow, m. 207° (81% yield) (oxime, m. 223°); Ac2O and AcONa convert this into 3,4-dicyano-2,5-dimethylpyrrole, m. 239° (89% yield); this yielded no phthalocyanine-like pigment when treated with metallic reagents under the usual conditions. 4-Carbethoxy-2,3-dimethylpyrrole-5-aldoxime on refluxing with Ac2O and AcONa gives 81% of Et 5-cyano-2,3-dimethylpyrrole-4-carboxylate, m. 180°; the free acid, m. 242°, decomposes 250°, results in 94% yield and could not be decarboxylated to the corresponding mononitrile. 2,3-Dimethylpyrrole was converted into the 5-formyl derivative and the 5-aldoxime, dehydrated to the 5-CN derivative, m. 121.5°, in 66% yield; this does not react with HCN and HCl, nor does the 5-aldoxime or 5-aldehyde. 5-Methylisoöxazole-3,4-dicarboxamide, m. 216°, results in 67% yield from the Et ester and NH4OH; P2O5 gives 70% of 3,4-dicyano-5-methylisoöxazole, b12 115°, b760 245° (some decomposition), m. 32°; about 3 hrs. heating at 115-20° and 5 mm. were necessary to form a pure product; HCl in absolute EtOH gives a mixture of the above Et ester and 3(or 4)-cyano-5-methylisoöxazole-3(or 4)-carboxamide, m. 225°; this also resulted with 10% KOH. The dinitrile did not form a phthalocyanine-like pigment. 3,6-Dimethylpyridazine-4,5-dicarboxamide, m. 240°, results in theoretical yield from the ester and NH4OH; sublimation at 240° and 10 mm. gives 44% of the imide, m. 240° (decomposition); the dinitrile could not be prepared and the imide did not yield a Cu pigment of the phthalocyanine type. Refluxing 2,5-dimethylfuran-3,4-dicarboxamide with Ac2O for 6 hrs: gives 4-cyano-2,5-dimethylfuran-3-carboxylic acid, m. 174°. Me 5-cyano-3-methylfuran-4-carboxylate, m. 49° (in 26% yield from the Ag salt and MeI), is hydrolyzed by concentrated NH4OH and is unchanged by EtOH-NH3 at 50° for 2 days. Dicyanotriazole does not yield pigments with metallic reagents; it is soluble in aqueous NaHCO3 with effervescence and a dilute aqueous solution dissolves Zn with evolution of H; the Ag salt, precipitated with AgNO3, is not dissolved by cautious addition of dilute HNO3; warming the Ag salt with excess HNO3 gives the free dinitrile; MeOH does not give a Me ether.
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, Category: triazoles.
Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics