title: Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution.
abstract: 2-(Alkyl(aryl)amino)thiazol-4(5H)-ones can regioselectively be prepared from monoalkyl(aryl)thioureas and maleimides. In solution, the former heterocycles exist in a tautomeric equilibrium with 2-(alkyl(aryl)imino)thiazolidin-4-ones and the substituent on the exocyclic nitrogen atom governs the ratio of these tautomers. Isomers with the alkyl group in the endocyclic position can be obtained fromN-methyl(ethyl)thioureas. 2D NMR spectroscopy and DFT calculations rationalize experimental results.
authors.affiliation: Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, Saint Petersburg, 198504, Russia.
authors.forename: Alena S
authors.initials: AS
authors.lastname: Pankova
authors.affiliation: Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, Saint Petersburg, 198504, Russia.
authors.forename: Pavel R
authors.initials: PR
authors.lastname: Golubev
authors.affiliation: Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, Saint Petersburg, 198504, Russia.
authors.forename: Alexander F
authors.initials: AF
authors.lastname: Khlebnikov
authors.affiliation: Centre for Magnetic Resonance, Saint Petersburg State University, Universitetsky pr. 26, Saint Petersburg, 198504, Russia.
authors.forename: Alexander Yu
authors.initials: AY
authors.lastname: Ivanov
authors.affiliation: Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, Saint Petersburg, 198504, Russia.
authors.forename: Mikhail A
authors.initials: MA
authors.lastname: Kuznetsov
keywords: maleimides; regioselectivity; tautomerism; thiazolidinones; thioureas