Title: Reaction of 5-halo-1,2,3-thiadiazoles with arylenediamines as a new approach to tricyclic 1,3,6-thiadiazepines
Authors: Volkova, NN ×
Tarasov, EV
Van Meervelt, Luc
Toppet, Suzanne
Dehaen, Wim
Bakulev, VA #
Issue Date: Jan-2002
Publisher: Royal soc chemistry
Series Title: Journal of the chemical society-perkin transactions 1 issue:13 pages:1574-1580
Abstract: A multistep reaction of 5-halo-1,2,3-thiadiazoles and 1,2-phenylenediamines provides a new route to fused 1,3,6-thiadiazepines. The overall process consists of the known stepwise formation of 5-[1-(2-aminophenyl)-1,2,3-triazol-5-ylsulfanyl]-1,2,3-thiadiazole, and a novel ring transformation which involves the Smiles and Dimroth rearrangements followed by an intramolecular nucleophilic substitution of the thiol group, affording di[1,2,3]triazolo[1,5-a:5',1'-d]-[3,1,5]benzothiadiazepines. The influence of the substituents on the 1,2,3-thiadiazole and phenyl rings on this reaction was discussed.
ISSN: 1472-7781
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
Biochemistry, Molecular and Structural Biology Section
× corresponding author
# (joint) last author

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