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Synthesis 2021; 53(13): 2219-2228
DOI: 10.1055/a-1372-1619
DOI: 10.1055/a-1372-1619
paper
Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones
We are grateful to the Faculty of Chemistry of Kharazmi University for supporting this work. Azim Ziyaei Halimehjani thanks the Alexander von Humboldt Foundation for supporting his research at the Albert-Ludwigs-Universität Freiburg. In addition, the project was financially supported by the Czech Academy of Sciences (RVO: 61388963).
Abstract
Thiazolidine-2-thiones were prepared via a novel multicomponent reaction of primary amines (amino acids), carbon disulfide, and γ-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.
Key words
dithiocarbamic acid - thiazolidine-2-thiones - amino acids - multicomponent reactions - taurine derivativesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1372-1619.
- Supporting Information
Publication History
Received: 28 November 2020
Accepted after revision: 25 January 2021
Accepted Manuscript online:
25 January 2021
Article published online:
24 February 2021
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