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Synthesis of 1,3-thiazolidine-2-thiones

Recent Literature

1,3-Thiazolidine-2-thiones can be prepared from β-amino alcohols and potassium ethylxanthate as the starting materials in the presence of ethanol.
Z. Lu, Y.-Q. Yang, W. Xiong, Synlett, 2019, 30, 713-716.

Amidato lanthanide amides were applied in the cycloaddition reactions of aziridines with carbon dioxide (CO₂) or carbon disulfide (CS₂) under mild conditions to provide the corresponding oxazolidinones and thiazolidine-2-thiones in good yields with good functional group tolerance.
Y. Xie, C. Lu, B. Zhao, Q. Wang, Y. Yao, J. Org. Chem., 2019, 84, 1951-1958.

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

Multicomponent reactions of CS₂, sulfoxonium ylides and secondary amines provide β-keto dithiocarbamates, whereas primary amines afforded thiazolidine-2-thiones or thiazole-2-thiones after dehydration in an acidic environment. These simple, versatile, and catalyst-free synthetic methods have a wide substrate scope and excellent functional group tolerance.
N. Kumar, A. Sharma, U. Kumar, S. K. Panday, J. Org. Chem., 2023, 88, 6120-6125.