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Synthetic approaches towards the sulfonamide substituted‐4,5‐diaryl‐4 H ‐1,2,4‐triazole‐3‐thiones
Author(s) -
Navidpour Latifeh,
Amini Mohsen,
Shafiee Abbas
Publication year - 2007
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.5570440614
Subject(s) - chemistry , substituent , sulfonamide , benzoic acid , aryl , sulfuric acid , alkylation , triazole , 1,2,4 triazole , medicinal chemistry , organic chemistry , combinatorial chemistry , alkyl , catalysis
A new series of 3‐alkylthio‐4,5‐diaryl‐4 H ‐1,2,4‐triazoles having a SO 2 NH 2 substituent in the para ‐position on one of the aryl rings ( 19/25 ) were prepared starting from the appropriate benzoic acid hydrazides ( 15/21 ). Reaction of the corresponding hydrazides with the appropriate isothiocyanates yielded 16/22 , which were cyclized in basic media to give 4,5‐diaryl‐2,4‐dihydro‐3 H ‐1,2,4‐triazole‐3‐thiones 17/23 . Alkylation of 17/23 afforded the alkylthio compounds 18/24 . Final debenzylation was achieved with concentrated sulfuric acid to give the target sulfonamides 19/25 .