Tetrahedron p. 1257 - 1270 (1993)
Update date:2022-08-04
Topics:
Zelenin
Kuznetsova
Alekseyev
Terentyev
Torocheshnikov
Ovcharenko
The condensation products from 4,4-dimethyl- and 2,4,4-trimethylthiosemicarbazides and aldehydes or ketones, as well as those from 2-methyl- and 2,4-disubstituted thiosemicarbazides and aldehydes have the thiosemicarbazone structure, while ketones react with 2-methyl- or 2,4-dialkylthiosemicarbazides to form 1,2,4- triazolidine- 3-thiones. Both thiosemicarbazones and 1,2,4- triazolidine- 3-thiones in trifluoroacetic acid solution yield 1,3,4-thiadiazolidine-2-iminium salts. Their deprotonation by pyridine leads to thiosemicarbazones, including otherwise inaccessible 2-methyl- and 2,4-disubstituted ketone thiosemicarbazones. The mass-spectrometric investigation of these compounds also suggests presence of their tautomers in the gas phase.
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