DABCO-Catalyzed Synthesis of Thiazolidine-2-thiones: System Development and Mechanistic Insights

A base-catalyzed protocol is reported for the construction of 1,3-thiazolidine-2-thione scaffolds bearing quaternary carbon centers from carbon disulfide and α-tertiary propargylamines. The reaction proceeds using low catalyst loading, under ambient temperatures, and in the absence of solvent. Various α-tertiary propargylamines have been employed, affording a series of previously unreported thiazolidine-2-thione compounds and avoiding purification via column chromatography in certain cases. We also describe a one-pot strategy for the synthesis of the same products through a KA2 coupling–CS2 incorporation approach. The reaction mechanism and substituent-dependent catalytic behavior were studied through a combination of detailed experimental and computational studies.

• Publication year

  2025

• Venue

  Journal of Organic Chemistry

• Publication date

  2025-03-19

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.joc.5c00020PMID 40105690PMCID 11959531
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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