Synthesis of heterocyclic compounds from 2-phenyl-1,2,3-triazole-4-formylhydrazine |
| |
Authors: | Fang-Ming Liu Jian-Xin Yu Wen-Jie Lu Gang Liu Yu-Ting Liu Yao-Zu Chen |
| |
Abstract: | 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 POCI3 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 POCI3 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. |
| |
Keywords: | 2-Phenyl-1, 2, 3-triazole 1, 3, 4- oxadiazole s-triazole [3, 4-b], 1, 3, 4-thiadiazole synthesis |
|
|