Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones

0541371 - ÚOCHB 2022 RIV DE eng J - Journal Article
Khalili Foumeshi, Maryam - Halimehjani, A. Z. - Alaei, A. - Klepetářová, Blanka - Beier, Petr
Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones.
Synthesis. Roč. 53, č. 13 (2021), s. 2219-2228. ISSN 0039-7881. E-ISSN 1437-210X
Institutional support: RVO:61388963
Keywords : dithiocarbamic acid * thiazolidine-2-thiones * amino acids * multicomponent reactions * taurine derivatives
OECD category: Organic chemistry
Impact factor: 3.019, year: 2021
Method of publishing: Limited access
https://doi.org/10.1055/a-1372-1619

Thiazolidine-2-thiones were prepared via a novel multicomponent reaction of primary amines (amino acids), carbon disulfide, and gamma-bromocrotonates. The reaction proceeds via a domino alkylation/intramolecular Michael addition to provide the corresponding thiazolidine-2-thiones in high to excellent yields. By using diamines in this protocol, bis(thiazolidine-2-thiones) derivatives were synthesized. The synthetic utility of the adducts was demonstrated by hydrolysis, amidation, and oxidation reactions.
Permanent Link: http://hdl.handle.net/11104/0318931