Synthesis of heierocyclic compounds from 2-phenyl-1, 2,3-triazole-4-formylhydrazine  

作　　者：刘方明 于建新 鲁文杰 刘罡 刘育亭 陈耀祖 

机构地区：[1]Department of Chemistry, Xinjiang University,Ulumuqi, Xingjing, 830046, China [2]Department of Chemistry, Xinjiang University,Ulumuqi, Xingjing, 830046, China Department of Chemical Engineering,Wuyi University,Jiangment,Guangdong 529020,China. [3]Department of Chemistry, Zhejiang University,Hangzhou, Zhejiang 310027, China

出　　处：《Chinese Journal of Chemistry》1999年第1期62-68,2,共8页中国化学（英文版）

基　　金：Project (No.29702007) supported by the National Natural Science Foundation of China.

摘　　要： 2-Phenyl-1, 2, 3-triazole-4-formylhydrazine (2) was prepared by hydrazinolysis of the corresponding ester 1. Reaction of 2 with CS2/KOH gave the oxadiazole derivatives (3) which via, Mannich reaction with different dialkyl amines furnished 3-N, N-dialkyl derivatives (4a-c). Also, condensation of 2 with appropriate aromatic acid in POCl3 yielded oxadiazole derivatives (5a-c), or with aldehydes and ketones afforded hydrazones (6a-c). Cyclization of (6a-c) with acetic anhydride gave the desired dihydroxadiazole derivatives (7a-c). On the other hand, reaction of dithiocarbazate (8) with hydrazine hydrate gave the corresponding triazole derivative (9) which on treatment with carboxylic acids in refluxing POCl3 yielded s-triazole[3,4-b]-1, 3, 4-thiadiazole derivatives (10a-b). The structures of all the above compounds were confirmed by means of IR, 1H NMR, MS and elemental analysis.2-Phenyl-1, 2, 3-triazole-4-formylhydrazine (2) was prepared by hydrazinolysis of the corresponding ester 1. Reaction of 2 with CS2/KOH gave the oxadiazole derivatives (3) which via, Mannich reaction with different dialkyl amines furnished 3-N, N-dialkyl derivatives (4a-c). Also, condensation of 2 with appropriate aromatic acid in POCl3 yielded oxadiazole derivatives (5a-c), or with aldehydes and ketones afforded hydrazones (6a-c). Cyclization of (6a-c) with acetic anhydride gave the desired dihydroxadiazole derivatives (7a-c). On the other hand, reaction of dithiocarbazate (8) with hydrazine hydrate gave the corresponding triazole derivative (9) which on treatment with carboxylic acids in refluxing POCl3 yielded s-triazole[3,4-b]-1, 3, 4-thiadiazole derivatives (10a-b). The structures of all the above compounds were confirmed by means of IR, 1H NMR, MS and elemental analysis.

关 键 词：2-Phenyl-1 2 3-triazole 1 3 4-oxadiazole s-triazole[3 4-b] 1 3 4-THIADIAZOLE synthesis 

分 类 号：O626[理学—有机化学]