54397-18-1

Upstream product

• 68-11-1 mercaptoacetic acid 
• 785-81-9 4-nitro-N-(phenylmethylene)benzenamine 
• 100-52-7 benzaldehyde 
• 100-01-6 4-nitro-aniline 
• 555-16-8 4-nitrobenzaldehdye 
• 1613-94-1 (E)-N-benzylidene-4-nitroaniline 
• 126079-75-2 [(4-Nitro-phenylamino)-phenyl-methylsulfanyl]-acetic acid 

Downstream Products

• 54477-20-2 5-(4-dimethylamino-benzylidene)-3-(4-nitro-phenyl)-2-phenyl-thiazolidin-4-one 

Relevant academic research and scientific papers

Ionic liquid immobilized on FeNi3 as catalysts for efficient, green, and one-pot synthesis of 1,3-thiazolidin-4-one

A magnetically ionic liquid (ILs) supported on FeNi3 nanocatalyst was synthesized and evaluated as a recoverable catalyst for the synthesis of 1,3-thiazolidin-4-one. The main targets are solvent-free conditions, rapid (immediately) and easy immobilization technique, and low cost precursors for the preparation of highly active and stable MPs with high densities of functional groups. The inorganic, magnetic, solid base catalyst was characterized via Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), transmission electron microscopy (TEM) and vibrating sample magnetometer (VSM). The catalyst is active for the synthesis of 1,3-thiazolidin-4-ones and the products are isolated in high to excellent yields. Supporting this base catalyst on magnetic particles offers a simple and non-energy-intensive method for recovery and reuse of the catalyst by applying an external magnet. Isolated catalysts were reused for new rounds of reactions without significant loss of their catalytic activity.

Preparation of thiazolidin-4-one derivatives using ZnO–NiO–NiFe2O4 nano-composite system

The hydrothermal synthesis of ZnO–NiO–NiFe2O4 nano-composite is reported. The sample was utilized to characterize via XRD, FE-SEM, EDS, FT-IR, UV–Vis, and BET techniques. The sample consisted of three different phases as ZnO (hexagonal), NiO (cubic), and NiFe2O4 (cubic) with the average particle size as 34?nm and specific surface area, average pore diameter, and pore volume as 64.35?m2?g?1, 13.02?nm, and 0.201?cm3?g?1, respectively. Catalytic behavior of the nano-composite was investigated on the synthesis of thiazolidin-4-one derivatives under thermal and ultrasonic irradiation condition. Our results show that the catalytic activity of ZnO–NiO–NiFe2O4 nano-composite is much higher than ZnO, NiO, and NiFe2O4 metal oxides. All products were prepared in high yields with short reaction times. In addition, the catalyst was recovered for at least five times.

Silica chloride (SiO2-Cl) catalyzed one pot synthesis of 2,3-disubstituted-thiazolidin-4-one

In this paper, we report one-pot, three-component cyclo condensation of an aldehyde, an amine and thioglycolic acid to form 2,3-disubstituted-thiazolidin-4-one by using supported protic acid (Silica Chloride: SiO2-Cl) catalyst. The catalyst SiO2-Cl is compatible with a variety of aldehydes (aryl/heteroaryl) and the aromatic amines affording 2,3-disubstituted-thiazolidin-4-one analogs in 72–89% yields. Moreover, the supported catalyst was recycled several times without significant loss of catalytical activity.

TS-1 zeolite as a Lewis acid catalyst for solvent-free one-pot synthesis of 1,3-thiazolidin-4-ones

Abstract: Titanium silicate (TS-1) zeolite heterogeneous catalyst is synthesized by the hydrothermally discontinuous method and is characterized by using XRD, SEM, TEM, and NH3–TPD techniques. The catalytic activity of the TS-1 type zeolite was tested for one-pot solvent-free synthesis of 1,3-thiazolidine-4-ones. The present technique illustrates many benefits, including eco-friendly reaction conditions, environmentally helpful, short response time, simplicity, straightforward separatation, catalyst reusability and high yields of the products. Furthermore, the catalyst was utilized for four recycle reactions and it has been found that the catalyst shows consistent chemical process activity. Graphical abstract: [Figure not available: see fulltext.].

An efficient alkynylation of 4-thiazolidinone with terminal alkyne under C-H functionalisation

A method of palladium catalysed efficient alkynylation through the cross coupling reaction of terminal alkynes with the slightly more acidic C-H bonds of 4-thiazolidinone has been developed. This method allows the direct introduction of an ethynyl group into the 4-thiazolidinone moiety. Mild reaction conditions involving aerial oxidation and one pot synthesis make this reaction more efficient for the formation of sp3(C)-sp(C) bond.

CoFe2O4@SiO2/PrNH2 nanoparticles as highly efficient and magnetically recoverable catalyst for the synthesis of 1,3-thiazolidin-4-ones

An efficient three-component synthesis of 1,3-thiazolidin-4-ones is described by one-pot condensation of aldehydes, aromatic amine and thioglycolic acid with nano-CoFe2O4@SiO2/PrNH2 as a robust heterogeneous catalyst. The significant advantages of this protocol are the use of magnetically recoverable catalyst, high to excellent product yields, operational simplicity and the use of CoFe2O4@SiO2/PrNH2 nanoparticles as an environment-friendly catalyst.

A catalysis study of mesoporous MCM-41 supported Schiff base and CuSO4·5H2O in a highly regioselective synthesis of 4-thiazolidinone derivatives from cyclocondensation of mercaptoacetic acid

Mesoporous MCM-41 supported Schiff base and CuSO4·5H2O shows high catalytic activity in the cyclocondensation of mercaptoacetic acid with imines (or aldehydes and amines) to afford pharmaceutically important thiazolidinone derivatives. The catalytic reactions involving two-components or three-components afforded the desired product in high yields (up to 98% and 99%). Moreover, the catalyst works well with respect to recyclability, giving the product in 85% and 83% yields after recycling six times.

Synthesis of 1,3-thiazolidin-4-one using ionic liquid immobilized onto Fe3O4/SiO2/Salen/Mn

An efficient and general method has been developed for synthesis of 1,3-thiazolidin-4-ones using magnetite nanoparticles immobilized Salen-Mn-ionic liquids as an efficient and recyclable catalyst. The inorganic, magnetic, solid base catalyst was characterized via N2 sorption, TEM, VSM, TGA, XRD, FTIR, and UV-vis. Nanocatalyst can be easily recovered by a magnetic field and reused for subsequent reactions for at least 6 times with less deterioration in catalytic activity.

Nano-Fe3O4@SiO2 supported ionic liquid as an efficient catalyst for the synthesis of 1,3-thiazolidin-4-ones under solvent-free conditions

A magnetically supported ionic liquid on Fe3O4@SiO2 nanoparticles (MNPs@ SiO2-IL) was synthesized and evaluated as a recoverable catalyst for the one-pot synthesis of 1,3-thiazolidin-4-ones in high to excellent yield under solvent-free conditions. The MNPs@SiO2-IL catalyst was characterized via Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), transmission electron microscopy (TEM) and vibrating sample magnetometer (VSM). Moreover, the catalyst could be easily recovered by magnetic separation and recycled for 10 times without significant loss of its catalytic activity.

Supported protic acid-catalyzed synthesis of 2,3-disubstituted thiazolidin-4-ones: Enhancement of the catalytic potential of protic acid by adsorption on solid supports

The catalytic potential of various protic acids has been assessed for the one pot tandem condensation-cyclisation reaction involving an aldehyde, an amine, and thioglycolic acid to form 2,3-disubstituted thiazolidin-4-ones. The catalytic potential of the various protic acids that follows the order TfOH > HClO4 > H2SO4 ～ p-TsOH > MsOH ～ HBF4 > TFA ～ AcOH is improved significantly by adsorption on solid supports, in particular using silica gel (230-400 mesh size), with the resulting relative catalytic potential following the order HClO 4-SiO2 > TfOH-SiO2 ? H2SO 4-SiO2 > p-TsOH-SiO2 > MsOH-SiO 2 ～ HBF4-SiO2 > TFA-SiO2 ～ HOAc-SiO2. The better catalytic potential of HClO 4-SiO2 as compared to that of Tf-SiO2, although TfOH is a stronger protic acid than HClO4, can be rationalised through a transition state model depicting the interaction of the individual protic acid with SiO2. The catalytic efficiency of HClO4 adsorbed on various solid supports was in the order HClO4-SiO 2 ? HClO4-K10 > HClO4-KSF > HClO 4-TiO2 ～ HClO4-Al2O3. The catalytic system HClO4-SiO2 is compatible with different variations of aldehydes (aryl/heteroaryl/alkyl/cycloalkyl) and the amines (aryl/heteroaryl/arylalkyl/alkyl/cycloalkyl) affording the desired 2,3-disubstituted thiazolidin-4-ones in 70-87% yields (43 examples). The electronic and the steric factors associated with the aldehydes and the amines provide a handle for selective thiazolidinone formation and were found to be dependent on the extent of imine formation. No significant amount of thiazolidinone formation took place during the reaction of the preformed amide (synthesised from the amine and thioglycolic acid) with benzaldehyde suggesting that the reaction proceeds through the initial reversible imine formation followed by cyclocondensation of the preformed imine with thioglycolic acid, the reversible imine formation being the determining step to control selectivity of thiazolidinone formation in competitive environments. The feasibility of a large scale reaction and catalyst recycling/reuse is demonstrated.