82417-76-3

Upstream product

• 82417-53-6 1-(Phenyl)-4-benzylidenamino-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-carbonsaeure-methylester 
• 82417-61-6 1-(Phenyl)-4-benzylidenamino-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-carbonsaeure 
• 82418-42-6 Methyl-2-benzylidenhydrazino-2-(phenylhydrazono)acetat 
• 82417-68-3 4-Benzylidenamino-2-(phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-on 
• 528585-21-9 α-[1,2,4]-triazolformylphenylhydrazine 

Relevant academic research and scientific papers

Studies on the reaction of α-chloroformylarylhydrazine hydrochloride with imidazole and 1,2,4-triazole

α-Imidazolformylarylhydrazine 2 and α-[1,2,4] triazolformylarylhydrazine 3 have been synthesized through the nucleophilic substitution reaction of 1 with imidazole and 1,2,4-triazole, respectively. 2,2′-Diaryl-2H,2′H-[4,4′]bi[[1,2,4]-triazolyl]-3, 3′-dione 4 was obtained from the cycloaddition of α- chloroformylarylhydrazine hydrochloride 1 with 1,2,4-triazole at 60 °C and in absence of n-Bu3N. The inducing factor for cycloaddition of 1 with 1,2,4-triazole was ascertained as hydrogen ion by the formation of 4 from the reaction of 3 with hydrochloric acid. 4 was also acquired from the reaction of 3 with 1 and this could confirm the reaction route for cycloaddition of 1 with 1,2,4-triazole. Some acylation reagents were applied to induce the cyclization reaction of 2 and 3. 1 possessing chloroformyl group could induce the cyclization of 2 to give 2-aryl-4-(2-aryl-4-vinyl-semicarbazide-4-yl)-2,4- dihydro-[1,2,4]-triazol-3-one 6. 7 was obtained from the cyclization of 2 induced by some acyl chlorides. Acetic acid anhydride like acetyl chloride also could react with 2 to produce 7D. 5-Substituted-3-aryl-3H-[1,3,4]oxadiazol-2-one 8 was produced from the cyclization reaction of 3 induced by some acyl chlorides or acetic acid anhydride. The 1,2,4-triazole group of 3 played a role as a leaving group in the course of cyclization reaction. This was confirmed by the same product 8 which was acquired from the reaction of 1, possessing a better leaving group: Cl, with some acyl chlorides or acetic acid anhydride.

Synthesis of 4-Amino-2-aryl-2,4-dihydro-3H-1,2,4-triazol-3-ones

The title compounds 10 are prepared in a multistep reaction sequence starting with alkyl 2-aryl-hydrazono-2-chloracetates 3 and aldehyde hydrazones 4.