Ring-Chain Tautomerism of N-Substituted Thiosemicarbazones

Autor: K. N. Zelenin, Valeriy V. Alekseyev, Olga B. Kuznetsova, Vladimir V. Ovcharenko, V. N. Torocheshnikov, Peter B. Terentyev
Rok vydání: 1993
Předmět:
Zdroj: Tetrahedron. 49:1257-1270
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)85816-6
Popis: 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.
Databáze: OpenAIRE