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

Literature Information

Publication Date 2013-07-23
DOI 10.1039/C3GC41218K
Impact Factor 10.182
Authors

Dinesh Kumar, Mukesh Sonawane, Brahmam Pujala, Varun K. Jain, Srikant Bhagat, Asit K. Chakraborti


View Original

Abstract

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 HClO4–SiO2 > TfOH–SiO2 ≫ H2SO4–SiO2 > p-TsOH–SiO2 > MsOH–SiO2 ∼ HBF4–SiO2 > TFA–SiO2 ∼ HOAc–SiO2. The better catalytic potential of HClO4–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–SiO2 ≫ HClO4–K10 > HClO4–KSF > HClO4–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.

Related Literature

Development of a ratiometric two-photon fluorescent probe for imaging of hydrogen peroxide in ischemic brain injury

Baoping Zhai, Wei Hu, Ruilin Hao, Wenjing Ni, Zhihong Liu

2019-08-21 Paper

DOI: 10.1039/C9AN01326A

A sensitive and versatile method for characterization of protein-mediated transformations of quantum dots

Magdalena Matczuk, Joanna Legat, Andrei R. Timerbaev, Maciej Jarosz

2016-03-15 Paper

DOI: 10.1039/C6AN00276E

Inside front cover

Cover

DOI: 10.1039/C9AN90096A

Spatially resolved endogenous improved metabolite detection in human osteoarthritis cartilage by matrix assisted laser desorption ionization mass spectrometry imaging

M. R. Eveque-Mourroux, P. J. Emans, R. R. M. Zautsen, A. Boonen, R. M. A. Heeren, B. Cillero-Pastor

2019-08-09 Paper

DOI: 10.1039/C9AN00944B

Convenient and controllable preparation of a novel uniformly nitrogen doped porous graphene/Pt nanoflower material and its highly-efficient electrochemical biosensing

Shuang Ren, Huan Wang, Yufan Zhang, Yuena Sun, Lanfen Li, Hongyi Zhang, Zhihong Shi, Mingjie Li, Meng Li

2016-03-11 Paper

DOI: 10.1039/C5AN02654G

Fullerenes in asphaltenes and other carbonaceous materials: natural constituents or laser artifacts

Vanessa G. Santos, Marcos A. Pudenzi, Clécio F. Klitzke, Heliara L. Nascimento, Rosana C. L. Pereira, Wagner L. Bastos, Marcos N. Eberlin

2016-01-07 Paper

DOI: 10.1039/C5AN02333E

Re-designing ferritin nanocages for mercuric ion detection

Yingjie Wang, Hai Chen, Jiachen Zang, Xiuqing Zhang, Guanghua Zhao

2019-08-19 Paper

DOI: 10.1039/C9AN01110B

A highly sensitive and simply operated protease sensor toward point-of-care testing

Seonhwa Park, Yu Mi Shin, Jeongwook Seo, Ji-Joon Song, Haesik Yang

2016-03-16 Paper

DOI: 10.1039/C6AN00251J

Efficient enantiorecognition of amino acids under a stimuli-responsive system: synthesis, characterization and application of electroactive rotaxane

Datong Wu, Fei Pan, Gao-Chao Fan, Ziming Zhu, Li Gao, Yongxin Tao, Yong Kong

2019-09-23 Paper

DOI: 10.1039/C9AN01692A

A colorimetric and fluorescent dual probe for palladium in aqueous medium and live cell imaging

Jin-wu Yan, Xiao-lin Wang, Qi-feng Tan, Pei-fen Yao, Jia-heng Tan, Lei Zhang

2016-03-11 Communication

DOI: 10.1039/C6AN00204H

You might also like

Compound Q&A

What precautions should be taken when handling 4-(2-Furylmethyl)thiomorpholine 1,1-dioxide (CAS: 79206-94-3)?

When handling 4-(2-Furylmethyl)thiomorpholine 1,1-dioxide (CAS: 79206-94-3), it ...

79206-94-34-(2-Furylmethyl)thi...
Compound Q&A

What precautions should be taken when handling 4-Chloro-N-[2-(4-morpholinyl)ethyl]benzamide (CAS: 71320-77-9)?

When handling 4-Chloro-N-[2-(4-morpholinyl)ethyl]benzamide (CAS: 71320-77-9), it...

71320-77-94-Chloro-N-[2-(4-mor...
Compound Q&A

How should waste containing 2-[2-(2-Methoxyethoxy)ethoxy]ethyl 4-methylbenzenesulfonate (CAS: 62921-74-8) be handled?

Waste containing this compound (CAS: 62921-74-8) should be handled according to ...

62921-74-82-[2-(2-Methoxyethox...
Compound Q&A

How should waste containing (S)-Methyl 2-amino-3-cyclohexylpropanoate be handled?

Waste containing (S)-Methyl 2-amino-3-cyclohexylpropanoate should be collected i...

40056-18-6(S)-Methyl 2-amino-3...
166882-70-85-({4-[(2S,4R)-4-Hyd...
Compound Q&A

Are there alternatives to (2E)-3-(3,4-Dichlorophenyl)acrylic acid (CAS: 7312-27-8) in synthesis?

There are several alternatives to (2E)-3-(3,4-Dichlorophenyl)acrylic acid in syn...

7312-27-8(2E)-3-(3,4-Dichloro...
Compound Q&A

How should Ethyl 6-(2-nitrophenyl)imidazo[2,1-b][1,3]thiazole-3-carboxylate (CAS: 925437-84-9) be stored?

Ethyl 6-(2-nitrophenyl)imidazo[2,1-b][1,3]thiazole-3-carboxylate (CAS: 925437-84...

925437-84-9Ethyl 6-(2-nitrophen...
Compound Q&A

How should waste containing 2-(1,3-Thiazol-2-yl)ethanamine (CAS: 18453-07-1) be handled?

Waste containing 2-(1,3-Thiazol-2-yl)ethanamine (CAS: 18453-07-1) should be coll...

18453-07-12-(1,3-Thiazol-2-yl)...
Compound Q&A

How is Methyl 5-iodo-2-methylbenzoate (CAS: 103440-54-6) typically synthesized?

Methyl 5-iodo-2-methylbenzoate can be synthesized through the iodination of meth...

103440-54-6Methyl 5-iodo-2-meth...
Compound Q&A

How is 5-Chloro[1,2,4]triazolo[1,5-a]pyridine (CAS: 1427399-34-5) typically synthesized?

5-Chloro[1,2,4]triazolo[1,5-a]pyridine is commonly synthesized via the condensat...

1427399-34-55-Chloro[1,2,4]triaz...

Source Journal

Green Chemistry

Green Chemistry
CiteScore: 16.1
Self-citation Rate: 7.5%
Articles per Year: 944

Green Chemistry provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on, but not limited to, the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998). Green chemistry is the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry is at the frontiers of this continuously-evolving interdisciplinary science and publishes research that attempts to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. Submissions on all aspects of research relating to the endeavour are welcome. The journal publishes original and significant cutting-edge research that is likely to be of wide general appeal. To be published, work must present a significant advance in green chemistry. Papers must contain a comparison with existing methods and demonstrate advantages over those methods before publication can be considered. For more information please see this Editorial. Coverage includes the following, but is not limited to: Design (e.g. biomimicry, design for degradation/recycling/reduced toxicity…) Reagents & Feedstocks (e.g. renewables, CO2, solvents, auxiliary agents, waste utilization…) Synthesis (e.g. organic, inorganic, synthetic biology…) Catalysis (e.g. homogeneous, heterogeneous, enzyme, whole cell…) Process (e.g. process design, intensification, separations, recycling, efficiency…) Energy (e.g. renewable energy, fuels, photovoltaics, fuel cells, energy storage, energy carriers…) Applications (e.g. electronics, dyes, consumer products, coatings, pharmaceuticals, preservatives, building materials, chemicals for industry/agriculture/mining…) Impact (e.g. safety, metrics, LCA, sustainability, (eco)toxicology…) Green chemistry is, by definition, a continuously-evolving frontier. Therefore, the inclusion of a particular material or technology does not, of itself, guarantee that a paper is suitable for the journal. To be suitable, the novel advance should have the potential for reduced environmental impact relative to the state of the art. Green Chemistry does not normally deal with research associated with 'end-of-pipe' or remediation issues.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.