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Research article · 2026 · Full text

International Journal of Advanced Chemistry Research

Comparative studies for the synthesis of aliphatic thiazolidinone derivatives from novel 1, 4 diaminobutane based dicationic ionic liquids

Nadeem AhmadPrashant Narayan Muskawar

Volume 8(5) · Pages 01–06 · DOI: 10.33545/26646781.2026.v8.i5a.669 ↗

Research areasMulticomponent Synthesis of HeterocyclesIonic liquids properties and applicationsChemical Synthesis and Reactions

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Abstract

Author-written

Most of the heterocyclic reactions are toxic and hazardous in nature in previous dates. The synthesis stratergies are continue to more attraction for the construction and development and find in wide range of applications in recent years with green chemistry. In this thiazolidinone are one the most active biological theme compounds and varying this study we perform a one pot three component synthesis route of greener method with aliphatic aldehyde and aromatic amines with Thioglycolic acid in presence of catalyst like Novel 1, 4 diaminobutane based dicationic ionic liquids. Which reduce reaction time. Its high range and easy recyclability abilities give high yield without any loss of its catalytic activity. Synthesis compound were confirm by TLC and its characterization like 1H-NMR, 13C-NMR, 19F-NMR, 31P-NMR, FT-IR. Allowing the product obtained with better identifications.

Summary

Source-checked

Plain-language reading of the full paper, prepared with AI and checked against the text. Each point links to the authors' own words.

  1. Why it matters

    • Thiazolidinone derivatives are important five-membered heterocycles because they exhibit a broad range of biological activities, such as anti-cancer, anti-viral, and anti-microbial properties. View evidence ↗

      Why it matters

      Thiazolidinone derivatives are important five-membered heterocycles because they exhibit a broad range of biological activities, such as anti-cancer, anti-viral, and anti-microbial properties.

      In the paper's own words

      “Thiazolidinone derivatives represent an significant class of sulfur- and nitrogen-containing five-membered heterocycles that have attracted considerable attention due to their wide spectrum of biological activities, including anti-cancer, anti-microbial, anti-inflammatory, anti-diabetic, and anti-viral properties”

      Page 1

      Found in: Text

      Read it in the full textOpen PDF at page 1 ↗
    • Traditional synthesis of these derivatives often relies on toxic organic solvents, which lead to environmental safety concerns, low yields, and long reaction times. View evidence ↗

      Why it matters

      Traditional synthesis of these derivatives often relies on toxic organic solvents, which lead to environmental safety concerns, low yields, and long reaction times.

      In the paper's own words

      “However, the use of toxic and volatile organic solvents are suffer from some several drawbacks in all methods including with prolonged reaction times, less product yield, low yields, which pose environmental and safety concerns”

      Page 1

      Found in: Text

      Read it in the full textOpen PDF at page 1 ↗
    • Dicationic ionic liquids (DCILs) are considered more sustainable than monocationic ionic liquids because they are easier to recover and reuse, reducing waste. View evidence ↗

      Why it matters

      Dicationic ionic liquids (DCILs) are considered more sustainable than monocationic ionic liquids because they are easier to recover and reuse, reducing waste.

      In the paper's own words

      “Dicationic ionic liquids can be easily recovered and reused more times than Monocationic ILs, thereby reducing waste products and improving process sustainability”

      Page 1

      Found in: Text

      Read it in the full textOpen PDF at page 1 ↗

  2. What they did

    • The researchers used a one-pot, three-component synthesis involving aliphatic aldehydes, aromatic amines, and thioglycolic acid. View evidence ↗

      What they did

      The researchers used a one-pot, three-component synthesis involving aliphatic aldehydes, aromatic amines, and thioglycolic acid.

      In the paper's own words

      “we perform a one pot three component synthesis route of greener method with aliphatic aldehyde and aromatic amines with Thioglycolic acid in presence of catalyst like Novel 1, 4 diaminobutane based dicationic ionic liquids.”

      Page 1

      Found in: Catalytic Studies

      Read it in the full textOpen PDF at page 1 ↗
    • The synthesized catalysts and thiazolidinone derivatives were characterized using 1H, 13C, 19F, and 31P NMR, as well as IR and mass spectroscopy. View evidence ↗

      What they did

      The synthesized catalysts and thiazolidinone derivatives were characterized using 1H, 13C, 19F, and 31P NMR, as well as IR and mass spectroscopy.

      In the paper's own words

      “The Dicationic Ionic liquid catalyst and All synthesized Aliphatic based Thiazolidinone derivatives were characterized using analytical techniques as 1H NMR and 13C NMR, 19F NMR,31P NMR, IR, Mass, spectroscopy.”

      Page 2

      Found in: Characterization

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  3. What they found

    • The [BDAMim](PF6-)2 catalyst consistently provided high yields between 92% and 98% within a short timeframe of 20 to 40 minutes. View evidence ↗

      What they found

      The [BDAMim](PF6-)2 catalyst consistently provided high yields between 92% and 98% within a short timeframe of 20 to 40 minutes.

      In the paper's own words

      “[BDAMim] (PF6 -)2 gives excellent yields (92-98%) in less time (20-40 Min.).”

      Page 4

      Found in: Catalytic Studies

      Read it in the full textOpen PDF at page 4 ↗
    • Compared to other methods, dicationic ionic liquids (DICLs) showed the best performance with yields of 90-98%, reaction times of 20-40 minutes, and reusability for 5-10 cycles. View evidence ↗

      What they found

      Compared to other methods, dicationic ionic liquids (DICLs) showed the best performance with yields of 90-98%, reaction times of 20-40 minutes, and reusability for 5-10 cycles.

      In the paper's own words

      “Dicationic ILs (DICLs) | 90-98 | R.T to 80 | 20 - 40 min | Yes (5-10 Cycles) | Highly green”

      Page 4

      Found in: Table 2

      Read it in the full textOpen PDF at page 4 ↗
    • The [BDAMim](PF6-)2 catalyst maintained its activity over seven consecutive runs without a significant decrease in yield. View evidence ↗

      What they found

      The [BDAMim](PF6-)2 catalyst maintained its activity over seven consecutive runs without a significant decrease in yield.

      In the paper's own words

      “where [BDAMim] (PF6-)2 has shown good catalytic activity across seven runs without a noticeable drop in yield.”

      Page 4

      Found in: Recycability

      Read it in the full textOpen PDF at page 4 ↗
    • Monocationic ionic liquids based on BF4 showed lower efficiency than DCILs, with yields of 80-90% and longer reaction times of 60-180 minutes. View evidence ↗

      What they found

      Monocationic ionic liquids based on BF4 showed lower efficiency than DCILs, with yields of 80-90% and longer reaction times of 60-180 minutes.

      In the paper's own words

      “The monocationic ionic liquid, represented by an 1,4 diaminobutane -based BF4 system exhibited moderate catalytic performance, affording product yields in the range of 80-90% with relatively longer reaction times (60-180 min).”

      Page 4

      Found in: Catalytic Studies

      Read it in the full textOpen PDF at page 4 ↗

  4. What it means

    • The authors conclude that their method provides a strong foundation for the next generation of green catalytic synthesis of aliphatic thiazolidinones. View evidence ↗

      What it means

      The authors conclude that their method provides a strong foundation for the next generation of green catalytic synthesis of aliphatic thiazolidinones.

      In the paper's own words

      “The strong foundation for development of next generation in heterocycles in green catalytic synthesis of aliphatic thiazolidinone.”

      Page 5

      Found in: Conclusion

      Read it in the full textOpen PDF at page 5 ↗
    • The authors recommend the use of [BDAMim](PF6-)2 due to its ability to retain catalytic activity over 5-10 cycles with negligible loss in yield. View evidence ↗

      What it means

      The authors recommend the use of [BDAMim](PF6-)2 due to its ability to retain catalytic activity over 5-10 cycles with negligible loss in yield.

      In the paper's own words

      “DCILs [BDAMim] (PF6 -) 2 retained its catalytic activity over 5-10 cycles with negligible loss in yield”

      Page 5

      Found in: Conclusion

      Read it in the full textOpen PDF at page 5 ↗

Visual summary

1 visuals

Illustrations explain the paper; they do not show study data.

AI-generated illustration
AI-generated conceptual illustration (aliphatic thiazolidinone molecules and dicationic ionic liquid catalyst). It explains the idea and does not show study data.↗ Enlarge
Catalyst Performance Comparison
AI-generated conceptual illustration (aliphatic thiazolidinone molecules and dicationic ionic liquid catalyst). It explains the idea and does not show study data.

AI-generated conceptual illustration (aliphatic thiazolidinone molecules and dicationic ionic liquid catalyst). It explains the idea and does not show study data.

Open full-size image ↗

Catalyst Performance Comparison

AI-generated conceptual illustration (aliphatic thiazolidinone molecules and dicationic ionic liquid catalyst). It explains the idea and does not show study data.

View source evidence ↗

Figures & tables

From the original paper
Optimization of synthesis of Thiazolidinone Derivatives synthesis.Table 1Page 3Advanced Comparison Table Catalyst performanceTable 2Page 4Comparative Recyclability of [BDAMim] (PF6-)2 inFigure 1Page 4
FULL TEXT Original article · reflowed for reading

Text

(DCILs) have attention for increasing and attraction to their superior physicochemical and catalytic properties compared to mono-cationic ionic liquids [12,14] . The attention shifted on Dicationic Ionic for the development of new subclass having two cationic centers linked by a flexible spacer, resulting they demonstrated lower toxicity and stronger electrostatic interactions, enhanced hydrogen bonding capability, and also improved thermal stability. These features highlight contribution to their enhanced catalytic efficiency and recyclability [13][14][15]31] . Particularly, heterocyclic synthesis with suitable for multicomponent reactions process making them catalytic active DILs [11,12,44] . In comparison, monocationic ionic liquids often exhibit lower catalytic activity than Dicationic ionic liquids and limited recyclability due to weaker ionic interactions [9] . The application of dicationic ionic liquids in the synthesis of aliphatic thiazolidinone derivatives has been extensively explored in recent decades. Several reports have demonstrated the efficient synthesis of thiazolidinone derivatives using Chloride and acetate based ionic liquids under mild and solvent-free conditions [12][13][14] . For instance, Dicationic liquid-mediated multicomponent reactions have been shown to produce aliphatic thiazolidinone in high yields with improved selectivity and shorter reaction times [13, 15, 32] . Most research scholar nowadays focusing on aromatic synthesis stratergies systems despite the advancement of synthesis of Aliphatic based thiazolidinone using DILs remains underexplore. Although, aliphatic compounds have more efficient catalytic system required for achieving the high yield and selectivity [3,5,44] . Therefore, the synthesis of aliphatic thiazolidinone using Dicationic ionic liquids is for the development of green and scalable employing methodologies and in significant and industrial interests. Herein, our goal is study green and efficient method for the synthesis of aliphatic based thiazolidinone derivatives using as catalyst i.e. 1, 4 diaminobiutane based dicationic ionic liquids (DCILs) these both catalyst and solvent have been employed. The best catalyst developed protocol offers. For the advancements, such as less reaction time, highest yield, and recyclability of Dicationic ionic liquid in environmentally benign conditions. The synthesized compounds were further characterization by using spectroscopic techniques including 1H NMR, 13C NMR, FT-IR, and mass spectrometry for confirming their structural identity.

Experimental 2.1. Materials

All reagents and chemicals were analytical grade and used without further purification and commercially available, 1,4 Diaminobutane, 1-Methyl Imidazole, Chloacetyl Chloride, Potassium Carbonate, Lithium Perchlorate and Potassium hexafluorophosphate were obtained from sigma Aldrich (India),sodium tetrafluoroborate, diethyl ether, Ethyl acetate, Sodium sulphate, Aldehydes, Primary aliphatic amines and Thioglycolic acid all chemical were purchase from S.D fine Chemicals and Co. Ltd. and Avra synthesis Pvt. Ltd. All the chemical were used as received unless it is specified all the glassware are special washed and dried under suitable temperature in Oven at 120 ºC to 150 ºC. TLC of the synthesized compound was taken on TLC Silica gel 60 F254 aluminum coated sheet. NMR Spectra of synthesized ionic liquids and products were recorded in DMSO-d 6 on a Brucker Spectrometer operating at 400 MHz and chemical shifts are given in ppm downfield from TMS (∂=0.00), FT-IR Spectra of the synthesized compounds were obtained by using Fourier Transform Infrared Spectrophotometer (Shimadzu, IR Affinity-1 Japan) in the wave range 400-4000cm -1 in the transmittance mode using KBr pellets.

Characterization

The Dicationic Ionic liquid catalyst and All synthesized Aliphatic based Thiazolidinone derivatives were characterized using analytical techniques as 1 H NMR and 13 C NMR, 19 F NMR, 31 P NMR, IR, Mass, spectroscopy. Also the melting points were measured for all synthesized derivatives.

Method 2.3.1 Scheme 1: 3, 3'-((butane-1,4diylbis(azanediyl)bis(2-oxoethne-2,1-diyl))bis(1-methyl-1H-imidazol-3-ium) dicationic Ionic Liquid.

Step -I: Alkylation of 1, 4 Diaminobutane According to lit. [45] N, N'-(butane-1,4-diyl)bis(2chloroacetamide) (2) known procedure with some minor modification and analytical data encounters with literature [15, 16] .

Synthesis of 3,3'-((butane-1,4diylbis(azanediyl)bis(2-oxoethne-2,1-diyl))bis(1-methyl-1H-imidazol-3-ium) chloride dicationic Ionic Liquid. (2a)

According to lit. [46] N, N'-(butane-1,4-diyl)bis(2chloroacetamide) (2) (2.41 g, 10 mmol) was loaded in R. B. flask with 1-methylimidazole (1.64 ml, 20 mmol) in 1:2 ration in 50 mL acetonitrile. Then taken on magnetic stirrer for next 24 hours under reflux condition. White sticky solid was obtained which separated by pouring of acetonitrile directly and rinsed ethyl acetate (3 x 20 ml) and finally followed by diethyl ether. After drying under high vacuum pure white solid of [EDAMIM] Cl 2 product was obtained. Yield:72%, White solid; M.p 94ºC; 1

Step -III: Metathesis of Anion 1) Synthesis of 3,3'-((butane-1,4-diylbis(azanediyl)0bis(2oxoethne-2,1-diyl))bis(1-methyl-1H-imidazol-3-ium) hexafluorophosphate dicationic Ionic Liquid. (2b)

The crude product was dissolve in Deionised water in minimum quantity and then add Potassium Hexafluoride (Dissolve in small quantity of deionised water) 1:2 ratio drop wise at room temperature and take it for continuous stirring for next 4 hours. After the completion of the reaction Ionic Liquid get Filter and then dry under high Vacuum. The White Solid soft Crystal are obtained. Yield: 92%, White solid; m.p 94 0 C; 1 [BDAMim] (PF 6 -) 2 was washed with ethyl acetate (3 x 5 mL), decanted and dried in oven at 60 ºC. Finally, Thiazolidinone derivative was isolated by removing ethyl acetate using rotary evaporator and solid product was purified by recrystallization in Methanol / Ethanol or some compounds were purified by column chromatography. The melting points and spectroscopic data of these thiazolidinone derivatives are in good concurrence with the literature.

Scheme 2: Synthesis of 2-butyl-3-phenylthiazolidin-4-one

Result and Discussion

The developed method successfully yielded aliphatic thiazolidinone derivatives with excellent efficiency.

Catalytic Studies

The present work exhibits a novel Dicationic based ionic liquid catalyst and solvent. The safe and simple method efficiently yielded thiazolidinone derivatives by using aniline, aliphatic aldehydes and Thioglycolic acid in 1:1:1.2 equimolar amount. The catalytic activity of [BDAMim] (PF 6 -) 2 catalyst as well as solvent examined towards the synthesis of thiazolidinone derivatives. In order to optimize reaction condition, the model reaction of Butyraldehyde aniline and Thioglycolic acid was carried out [BDAMim] (PF 6 -) 2 Dicationic ionic liquid. The activities of the catalyst were evaluated by varying the amount of catalyst, reaction temperature and time. (Table 1). Nano catalyst and conventional while still outperforming the monocationic system, exhibited slightly lower efficiency (4 -12 hrs and 3-6hrs) with (70-80% yield; 50-70% yield) compared to. To the MILs and DCILs may be due to the absence of an aromatic cationic system, leading to weaker intermolecular interactions and less effective catalytic activation. Overall Comparisons of Dicationic ionic liquids exhibit significantly enhanced catalytic performance as compared to Monocationic ionic liquids, Nano catalyst and Conventional (Acid / Base) method in the synthesis of aliphatic thiazolidinone. Dicationic ionic liquids showed higher catalytic activity with their dual ionic nature provides improved interaction with reactants, leading to higher yields, faster reactions, and better sustainability as compared to conventional solvents and Monocationic ILs Recyclability up to 4-5 cycles, Therefore, DILs are more suitable for advanced green synthetic and Recyclability up to 5-10 cycles remain superior in catalytic applications.

Table 1. Optimization of synthesis of Thiazolidinone Derivatives synthesis.
Optimization of synthesis of Thiazolidinone Derivatives synthesis.↗ Enlarge
Table 1
Optimization of synthesis of Thiazolidinone Derivatives synthesis.

Optimization of synthesis of Thiazolidinone Derivatives synthesis.

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Original paper figureSource PDF · page 3 ↗

Recycability

The recyclability of the solvent/catalyst [BDAMim] (PF 6 -) 2 was investigated in the model reactions of Butyraldehyde,, Aniline and thioglycolic acid. After every run, thiazolidinone was diluted with ethyl acetate, and the [BDAMim] (PF 6 -) 2 was obtained by solvent decantation. Any leftover traces of the non-ionic compounds were removed by washing with ethyl acetate and diethyl ether. After being vacuum-dried for three hours at 60 °C, the [BDAMim] (PF 6 -) 2 was used for the next run of the model reaction. Our catalyst is recyclable, as shown by Fig. 1, where [BDAMim] (PF 6 -) 2 has shown good catalytic activity across seven runs without a noticeable drop in yield.

Figure 1. Comparative Recyclability of [BDAMim] (PF6-)2 in
Comparative Recyclability of [BDAMim] (PF6-)2 in↗ Enlarge
Figure 1
Comparative Recyclability of [BDAMim] (PF6-)2 in

Comparative Recyclability of [BDAMim] (PF6-)2 in

Open full-size image ↗
Original paper figureSource PDF · page 4 ↗

Acknowledgement

The authors are grateful to Management and Principal of Amolakchand Mahavidyalaya, Yavatmal for providing the laboratory facilities. We are acknowledged VIT University, Vellore, for providing instrumental facilities for characterization.

Conclusion

Recyclability studies further highlighted the advantages of dicationic ionic liquids. DCILs [BDAMim] (PF 6 -) 2 retained its catalytic activity over 5-10 cycles with negligible loss in yield, whereas [EDAMim] (BF 4 -) 2 showed moderate stability up to 3-5 cycles. In comparison, the monocationic ionic liquid displayed a significant decrease in the other acid / base or nano catalyst methods activity after 2-3 cycles. The strong foundation for development of next generation in heterocycles in green catalytic synthesis of aliphatic thiazolidinone. The synthesis stratergies are continue to more attraction in future for the construction and developments are found in wide range of applications.

Figures and tables from the paper

Table 2. Advanced Comparison Table Catalyst performance
Catalyst TypeYield%Temp (0C)Time (min.-hour)ReusabilityEnvironmental
Conventional (Acid / Base)50-7070-1204-12 hrsNoToxic Nature Solvents
Catalyst (Nano)70-8060-1003-6 hrs.ModerateSemi-green
Mono Ionic Liquid(MILs)80-9340-701-3 hrsYes (3-5 Cycles)Green
Dicationic ILs (DICLs)90-98R.T to 8020 - 40 minYes (5-10 Cycles)Highly green

Table text extracted from the original PDF; superscript letters are shown inline. The original table image is below.

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Advanced Comparison Table Catalyst performance↗ Enlarge
Table 2
Advanced Comparison Table Catalyst performance

Advanced Comparison Table Catalyst performance

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Original paper tableSource PDF · page 4 ↗

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