57178-09-3

Upstream product

• 108-94-1 cyclohexanone 
• 68-11-1 mercaptoacetic acid 
• 62-53-3 aniline 
• 1132-38-3 N-cyclohexylidenebenzenamine 
• 30298-36-3 2-mercaptothioacetic acid 

Downstream Products

• 154599-30-1 2-(2'-oxo-3'-indolylidene)-1-thia-4-phenyl-4-azaspiro<4.5>decan-3-one 
• 164408-15-5 2-[1-(4-Nitro-phenyl)-3-oxo-3-phenyl-propyl]-4-phenyl-1-thia-4-aza-spiro[4.5]decan-3-one 
• 164408-13-3 2-[1-(4-Chloro-phenyl)-3-oxo-3-phenyl-propyl]-4-phenyl-1-thia-4-aza-spiro[4.5]decan-3-one 
• 164408-14-4 2-[1-(4-Methoxy-phenyl)-3-oxo-3-phenyl-propyl]-4-phenyl-1-thia-4-aza-spiro[4.5]decan-3-one 
• 99223-59-3 2,4-Diphenyl-1-thia-4-aza-spiro[4.5]decan-3-one 
• 99223-56-0 Acetic acid 3-oxo-4-phenyl-1-thia-4-aza-spiro[4.5]dec-2-yl ester 
• 1246086-90-7 C₂₀H₂₇NO₆S 
• 164408-12-2 2-(3-Oxo-1,3-diphenyl-propyl)-4-phenyl-1-thia-4-aza-spiro[4.5]decan-3-one 

Relevant academic research and scientific papers

Facile synthesis of spiro thiazolidinone via cyclic ketones, amines and thioglycolic acid by MCM-41-Schiff base-CuSO4·5H2O

Mesoporous MCM-41-supported Schiff base and CuSO4?5H2O (MCM-41@Schiff base-CuSO4?5H2O) catalyzed one-pot three-component condensation of cyclic ketones, amines and thioglycolic acid in toluene. And a series of corresponding spiro thiazolidinone derivatives were obtained in high yields (up to 97%). The synthesized catalyst was characterized via FT-IR, XRD, SEM, TEM and EDS and can be easily recovered by centrifugation and reused at 10 times without any change in catalytic activity. Moreover, the scale-up experiment also demonstrated the practicability of the catalytic system on the condensation. The possible mechanisms pave the way to investigation on the reactions of other cyclic ketones with thioglycolic acid.

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.

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.

Facile novel synthesis and reactions of thiazolidin-4-one derivatives for antimicrobial agents

A facile and fast procedure for synthesis of 3-phenyl-cyclohexane(1'-2) thiazolidin-4-one (1), which underwent condensation with glucose and p-chlorobenzaldehyde to afford 2 and 3, respectively. Compound 3 was used as precursor for the preparation of some

A brief survey of the use of the Pummerer rearrangement for the alkylation of 1,3-oxathiolan-5-ones and 1,3-thiazolidin-4-ones

Oxidation of 1,3-oxathiolan-5-ones (1) gives acceptable yields of sulfoxides only when C4 is unsubstituted.Sulfoxides derived from 1,3-thiazolidine-4-ones (8) are easily prepared.Acid-catalyzed rearrangement in the presence of 1-alkenes or benzene leads t