528585-22-0Relevant academic research and scientific papers
Studies on the reaction of α-chloroformylarylhydrazine hydrochloride with imidazole and 1,2,4-triazole
Chiu, Chun-Yen,Chung, Jen-Hua,Kuo, Wen-Fa,Yeh, Mou-Yung
, p. 1003 - 1014 (2007/10/03)
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.
