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Multicomponent Reaction of CS2, Amines, and Sulfoxonium Ylides in Water: Straightforward Access to β-Keto Dithiocarbamates, Thiazolidine-2-thiones, and Thiazole-2-thiones

Naveen Kumar, Ajay Sharma, Upendra Kumar and Satyendra Kumar Pandey*

*Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221 005, India, Email: skpandey.chembhu.ac.in

N. Kumar, A. Sharma, U. Kumar, S. K. Panday, J. Org. Chem., 2023, 88, 6120-6125.

DOI: 10.1021/acs.joc.2c02763


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Abstract

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.


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proposed mechanism



Key Words

dithiocarbamates (S-alkylation, amination, thiazolidine-2-thiones, thiazole-2-thiones, multicomponent reactions


ID: J42-Y2023