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

Maryam Khalili Foumeshi; Azim Ziyaei Halimehjani; Ali Alaei; Blanka Klepetářová; Petr Beier

doi:10.1055/a-1372-1619

Synthesis, Table of Contents

Synthesis 2021; 53(13): 2219-2228
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

Maryam Khalili Foumeshi

^aFaculty of Chemistry, Kharazmi University, P. O. Box 15719-14911, 49 Mofateh Street, Tehran, Iran

^bInstitute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic

,

Azim Ziyaei Halimehjani ∗

^aFaculty of Chemistry, Kharazmi University, P. O. Box 15719-14911, 49 Mofateh Street, Tehran, Iran

^cInstitut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstr. 21, 79104 Freiburg im Breisgau, Germany

,

Ali Alaei

^aFaculty of Chemistry, Kharazmi University, P. O. Box 15719-14911, 49 Mofateh Street, Tehran, Iran

,

Blanka Klepetářová

^bInstitute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic

,

Petr Beier∗

^bInstitute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic

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Abstract

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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 derivatives

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References

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