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Synthesis, X‐ray crystal structure and biological activities of α‐phenoxyl‐1,2,3‐thiadiazoleacetamide
Author(s) -
Zhao Wei Guang,
Li Zheng Ming,
Yang Zhao
Publication year - 2003
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570400529
Subject(s) - acetamide , chemistry , thionyl chloride , annulation , crystal structure , derivative (finance) , phenols , x ray , crystal (programming language) , phenol , medicinal chemistry , chloride , stereochemistry , crystallography , organic chemistry , catalysis , physics , quantum mechanics , computer science , financial economics , programming language , economics
The annelation of 1,2,3‐thiadiazole rings was accomplished by the reaction of N ‐acylhydrazone 2a bearing an adjacent α‐methyl with thionyl chloride to give α‐chloro‐ N ‐methyl‐1,2,3‐thiadiazole‐4‐acetamide 4 and was demonstrated by the X‐ray crystal structure of its derivative 5a. A novel series of α‐substituted phenoxy‐ N ‐methyl‐1,2,3‐thiadiazole‐4‐acetamide 5 were synthesized through the reaction of the compound 4 and phenols. The results of bioassays show that the title compounds exhibit good anti‐HBV activities. The crystal of compound 5a , N ‐methyl‐α‐2‐bromophenyl‐1,2,3‐thiadiazole‐4‐acetamide, has been prepared and determined by X‐ray diffraction.