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Synthesis of heterocyclic compounds from 2‐phenyl‐1,2,3‐triazole‐4‐formylhydrazine
Author(s) -
Liu FangMing,
Yu JianXin,
Lu WenJie,
Liu Gang,
Liu YuTing,
Chen YaoZu
Publication year - 1999
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19990170109
Subject(s) - chemistry , hydrazine (antidepressant) , acetic anhydride , hydrate , 1,2,4 triazole , mannich reaction , acetic acid , organic chemistry , medicinal chemistry , oxadiazole , triazole , derivative (finance) , condensation reaction , elemental analysis , catalysis , chromatography , financial economics , economics
2‐Phenyl‐1, 2, 3‐triazole‐4‐formylhydrazine (2) was prepared by hydrazinolysis of the corresponding ester 1. Reaction of 2 with CS 2 /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 POCI 3 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 POCI 3 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, 1 H NMR, MS and elemental analysis.