Expedient synthesis of novel antibacterial hydrazono-4-thiazolidinones under catalysis of a natural-based binary ionic liquid

  • Maedeh Saeedi Mirakmahaleh
  • Kurosh Rad-MoghadamEmail author
  • Hassan Kefayati
  • Soroush Falakro
Original Article


A library of pyran-2H-one-3-ylmethylidene and chromene-2H-one-3-ylmethylidene derivatives of the titled heterocyclic framework was synthesized from 3-acyl-4-hydroxypyran/chromene-2H-one via sequential reaction with thiosemicarbazide and dialkyl acetylenedicarboxylates. The syntheses were carried out under efficient catalysis of a new binary ionic liquid mixture [l-prolinium chloride][1-methylimidazolium-3-sulfonate] in one pot and solvent-free conditions. Calculations based on density functional theory displayed that the barrier energy for interconversion of the two possible diastereomeric isomers of each product is less than the thermal energy of molecules at room temperature, as only one product can be resolved from a given reaction mixture. This seems to be the case for the previously reported hydrazonothiazolidines. The binary ionic liquid mixture melts at near room temperature and can be considered as a solution of HCl in 1:1 mixture of two zwitterionic species. It proved to be more efficient than its constituents in catalyzing the above synthesis in one-pot operation. Some of the synthesized products have shown pronounced antibacterial activities. The ionic liquid is virtually stable in air and moisture, as can be retrieved several times without appreciable decrease in its catalytic activity.

Graphic abstract


Thiazolidin-4-one Binary ionic liquid 4-Hydroxypyran-2H-one 4-Hydroxychromene-2H-one Homogeneous catalysis 



Ionic liquid


Binary ionic liquid




1-Methyl-3-sulfonylimidazolium chloride




l-Prolinium chloride


Hexadeuterated dimethylsulfoxide


para-Toluenesulfonic acid




Density functional theory



Support of this work by the Research Council of University of Guilan is gratefully acknowledged.

Supplementary material

11030_2019_10028_MOESM1_ESM.docx (3.7 mb)
Supplementary material 1 (DOCX 3815 kb)


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Copyright information

© Springer Nature Switzerland AG 2020

Authors and Affiliations

  1. 1.Chemistry DepartmentUniversity of GuilanRashtIran
  2. 2.Chemistry DepartmentIslamic Azad University, Rasht BranchRashtIran

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