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

Savvas G Chalkidis, Sungil Hong, Anthi-Markella Tsiadi, Evangelia Fika, Nikolaos Tsoureas, Giannis Mpourmpakis, Georgios C Vougioukalakis

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Article in The Journal of organic chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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7 authors.

Savvas G ChalkidisLaboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, Athens 15784, Greece.

Sungil HongDepartment of Chemical and Petroleum Engineering, University of Pittsburgh, Pittsburgh, Pennsylvania 15261, United States.

Anthi-Markella TsiadiLaboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, Athens 15784, Greece.

Evangelia FikaLaboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, Athens 15784, Greece.

Nikolaos TsoureasLaboratory of Inorganic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Athens 15784, Greece.ORCID 0000-0003-0262-9382

Giannis MpourmpakisDepartment of Chemical and Petroleum Engineering, University of Pittsburgh, Pittsburgh, Pennsylvania 15261, United States.ORCID 0000-0002-3063-0607

Georgios C VougioukalakisLaboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, Athens 15784, Greece.ORCID 0000-0002-4620-5859

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6 · The paper itself

Abstract

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 KA

Identifiers

PMID40105690

DOI10.1021/acs.joc.5c00020

PMCPMC11959531

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