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Synthesis of 1,3-thiazolidine-2-thiones using CS2 and epoxy amines

Ziyaei Halimehjani , A ; Sharif University of Technology | 2024

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Type of Document: Article
DOI: 10.1016/j.tetlet.2024.155361
Publisher: 2024
Abstract:
An efficient method for the synthesis of 5-(hydoxymethyl)-1,3-thiazolidine-2-thiones is developed via the reaction of carbon disulfide with N-alkyl(aryl) epoxy amines. The reaction proceeds via intramolecular epoxide ring opening with in situ prepared dithiocarbamic acid. The products were obtained in good to high yields. © 2024 Elsevier Ltd
Keywords:
Dithiocarbamate ; Thiazolidinethiones ; 1,2 amino alcohol ; 1,2 amino thiol ; 1,3 thiazolidine 2 thione ; 2,3 epoxypropyl alkyl(aryl)amine ; 2,3 epoxypropyl amine ; 3 cyclohexyl 5 (hydroxyl methyl)thiazolidine 2 thione ; 5 (hydoxymethyl) 1,3 thiazolidine 2 thione ; Alcohol ; Amine ; Azetidine ; Aziridine ; Carbon disulfide ; Dithiocarbamic acid ; Epoxide ; Epoxy amine ; Functional group ; Iminothiazolidine ; N alkyl(aryl) epoxy amine ; Oxazolidinone ; Oxazolidinone derivative ; Pyrrolidine derivative ; Thiazolidine ; Thiazolidine derivative ; Unclassified drug ; Asymmetric synthesis ; Carbon nuclear magnetic resonance ; Chemical structure ; Crystallization ; Cyclization ; Drug synthesis ; Hydrogen bond ; Nucleophilicity ; Proton nuclear magnetic resonance ; Ring opening ; Transmission electron microscopy
Source: Tetrahedron Letters ; Volume 152 , 2024 ; 00404039 (ISSN)
URL: https://www.sciencedirect.com/science/article/abs/pii/S0040403924004568