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

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Abstract

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.

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Scheme 1
Scheme 2
Fig. 1
Scheme 3
Scheme 4
Scheme 5

Abbreviations

IL:

Ionic liquid

BIL:

Binary ionic liquid

MImS:

3-Methylimidazolium-1-sulfonate

[MSIm]Cl:

1-Methyl-3-sulfonylimidazolium chloride

BMIm:

1-Butyl-3-methylimidazolium

LPC:

l-Prolinium chloride

DMSO-d 6 :

Hexadeuterated dimethylsulfoxide

p-TSA:

para-Toluenesulfonic acid

DMAD:

Dimethylacetylenedicarboxylate

DFT:

Density functional theory

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Acknowledgement

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

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Correspondence to Kurosh Rad-Moghadam.

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Mirakmahaleh, M.S., Rad-Moghadam, K., Kefayati, H. et al. Expedient synthesis of novel antibacterial hydrazono-4-thiazolidinones under catalysis of a natural-based binary ionic liquid. Mol Divers (2020) doi:10.1007/s11030-019-10028-7

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Keywords

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