100727-37-5Relevant academic research and scientific papers
Condensation–cyclization reaction for one-pot synthesis of 1,3-thiazolidin-4-one derivatives by poly(p-phenylenediamine) grafted on LDHs as a catalyst with green tool
Mirzaei-Mosbat, Maryam,Ghorbani-Vaghei, Ramin
, p. 83 - 95 (2021)
The three-component reaction between amine, carbonyl compound and thioglycolic acid is now considered as a major strategy for synthesis of 1,3-thiazolidin-4-ones, which consists of the following steps: (i) condensation of aldehyde and amine which results
Silica chloride (SiO2-Cl) catalyzed one pot synthesis of 2,3-disubstituted-thiazolidin-4-one
Gokhale, Kunal M.,Telvekar, Vikas N.
, p. 1396 - 1403 (2020)
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.
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
Kumar, Dinesh,Sonawane, Mukesh,Pujala, Brahmam,Jain, Varun K.,Bhagat, Srikant,Chakraborti, Asit K.
, p. 2872 - 2884 (2013/10/08)
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.
