One-Pot Three-Component Synthesis of 2-Imino-1,3-Thiazolines on Soluble Ionic Liquid Support

Chan Yu Chen, Indrajeet J. Barve, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

An efficient one-pot, three-component synthesis of 2-imino-1,3-thiazolidines and 2-imino-1,3-thiazolines using ionic liquid-tethered 2-aminobenzimidazoles was reported. The protocol includes reaction of ionic liquid attached 2-aminobenzimidazoles with isothiocyanates to afford isothioureas, followed by its base induced inter and intramolecular nucleophilic displacement reactions with 1,2-dichloroethane (EDC) which results in thiazolidine ring formation. In the next to the last step, the ionic liquid support was removed by methanolysis to deliver 2-imino-1,3-thiazolidines, which were sequentially oxidized with manganese(III) triacetate to yield 2-imino-1,3-thiazolines. The salient feature of this method is the use of 1,2-dichloroethane as a synthetic equivalent for α-haloketone to avoid the use of toxic halogenating reagents.

Original languageEnglish
Pages (from-to)638-643
Number of pages6
JournalACS Combinatorial Science
Volume18
Issue number10
DOIs
StatePublished - 10 Oct 2016

Keywords

  • 1,2-dichloroethane
  • 2-imino-1,3-thiazolines
  • ionic liquid support
  • one pot

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