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Tosylation of 2‐(monosubstituted)amino‐1,3,4‐thiadiazoles
Author(s) -
L'abbé Gerrit,
Verhelst Gabriel,
Huybrechts Lucas,
Toppet Suzanne
Publication year - 1977
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.5570140333
Subject(s) - thiadiazoles , chemistry , acetylation , triethylamine , ring (chemistry) , tautomer , stereochemistry , organic chemistry , biochemistry , gene
Tosylation of 2‐benzylamino‐ and 2‐anilino‐5‐phenyl‐1,3,4‐thiadiazoles ( 1a,b ) in the presence of triethylamine affords the ring‐sulfonylated products 2a,b which isomerize in a later stage of the reaction to the exocyclic amino‐sulfonylated products 3a,b . Acetylation of 1a,b gives the acylamino substituted thiadiazoles 4a,b directly as the only reaction products. The 13 C nmr data are discussed and their importance for the study of prototropic tautomerism and for structure elucidation of the reaction products is indicated.