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*

*Kharazmi University, P. O. Box 15719-14911, 49 Mofateh Street, Tehran, Iran; Czech Academy of Sciences, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic, Email: ziyaeikhu.ac.ir, beieruochb.cas.cz

M. K. Foumeshi, A. Z. Halimehjani, A. Alaei, B. Klepetářová, P. Beier, Synthesis, 2021, 53, 2219-2228.

DOI: 10.1055/a-1372-1619

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Abstract

A multicomponent reaction of primary amines (amino acids), carbon disulfide, and γ-bromocrotonates provides thiazolidine-2-thiones in excellent yields via a domino alkylation/intramolecular Michael addition. The synthetic utility of the adducts was demonstrated by hydrolysis, amidation, and oxidation reactions.

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Key Words

dithiocarbamic acid, thiazolidine-2-thiones, amino acids, multicomponent reactions, taurine derivatives

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ID: J66-Y2021