Citation: Naser Foroughifar, Sattar Ebrahimi. One-pot synthesis of 1, 3-thiazolidin-4-one using Bi(SCH₂COOH)₃ as catalyst[J]. Chinese Chemical Letters, ;2013, 24(05): 389-391. shu

One-pot synthesis of 1, 3-thiazolidin-4-one using Bi(SCH₂COOH)₃ as catalyst

Naser Foroughifar ^a,, ,
Sattar Ebrahimi ^b,,

1.
a Faculty of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran;
2.
b Department of Chemistry Malayer Branch, Islamic Azad University, Malayer, Iran

Corresponding author: Naser Foroughifar, Sattar Ebrahimi,
Received Date: 17 December 2012
Available Online: 5 March 2013

A catalytic multi-component reaction involving aromatic amine, aromatic aldehydes, mercapto acid as substrates and Bi(SCH₂COOH)₃ as catalyst under solvent free conditions, afforded thiazolidin-4-one in good yields. The efficiency of the catalyst was proved with a variety of substrates, ranging from electrondeficient to electron-rich aldehydes.
- Thiazolidin-4-one,
- Mercapto acid,
- Multicomponent,
- Thioglycolic acid
1. [1]
  [1] S. Samai, G.C. Nandi, R. Kumar, M.S. Singh, Multicomponent one-pot solvent-free synthesis of functionalized unsymmetrical dihydro-1H-indeno[1,2-b]pyridines, Tetrahedron Lett. 50 (2009) 7096-7098.
2. [2]
  [2] Y.X. Li, X. Zhai, W.K. Liao, et al., Design, synthesis and biological evaluation of new rhodacyanine analogues as potential antitumor agents, Chin. Chem. Lett. 23 (2012) 415-418.
3. [3]
  [3] D. Bhambi, V.K. Salvi, J.L. Jat, S. Ojha, G.L. Talesara, Synthesis and antimicrobial activity of some new indole containing isoxazolines and phthalimidoxy derivatives of thiazolidinone and thiohydantoin, J. Sulfur Chem. 28 (2007) 155-163.
4. [4]
  [4] X. Zhang, X. Li, D. Li, et al., Ionic liquid mediated and promoted eco-friendly preparation of thiazolidinone and pyrimidine nucleoside-thiazolidinone hybrids and their antiparasitic activities, Bioorg. Med. Chem. Lett. 19 (2009) 6280-6283.
5. [5]
  [5] A. Mobinikhaledi, N. Foroughifar, M. Kalhor, et al., Synthesis and antifungal activity of novel 2-benzimidazolylimino-5-arylidene-4-thiazolidinones J, Heterocycl. Chem. 47 (2010) 77-80.
6. [6]
  [6] X. Jin, C.J. Zheng, M.X. Song, et al., Synthesis and antimicrobial evaluation of lphenylalanine-derived C5-substituted rhodanine and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone, Eur. Med. Chem. 56 (2012) 203-209.
7. [7]
  [7] X.J. Sun, W.L. Dong, W.G. Zhao, Z.M. Li, Synthesis, crystal structure and biological activities of 2-substituted-3-aryl-4-thiazolidinone(thiazolidinethione) derivatives, Chin. J. Org. Chem. 27 (2007) 1374-1380.
8. [8]
  [8] B. Chandrasekhar, b-Mercaptoalkanoic carboxylic esters: versatile synthons in heterocyclic chemistry, J. Sulfur Chem. 29 (2008) 187-240.
9. [9]
  [9] D. Gautam, P. Gautam, R.P. Chaudhary, N-methylpyridinium tosylate catalyzed green and efficient synthesis of some novel 2,4-disubstituted thiazoles and 4-thiazolidinones, Chin. Chem. Lett. 23 (2012) 1221-1224.
10. [10]
  [10] S.G. Patil, R.R. Bagul, M.S. Swami, et al., Synthesis of 5-benzylidene-3-(3-fluoro-4-yl-morpholin-4-yl-phenylimino)thiazolidin-4-one derivatives catalyzed by[BmIm]OH and their anti-microbial activity, Chin. Chem. Lett. 22 (2011) 883-886.
11. [11]
  [11] V. Gududuru, V. Nguyen, J.T. Dalton, D.D. Miller, Efficient microwave enhanced synthesis of 4-thiazolidinones, Synlett (2004) 2357-2358.
12. [12]
  [12] U.R. Pratap, D.V. Jawale, M.R. Bhosle, R.A. Mane, Saccharomyces cerevisiae catalyzed one-pot three component synthesis of 2,3-diaryl-4-thiazolidinones, Tetrahedron Lett. 52 (2011) 1689-1691.
13. [13]
  [13] A. Bolognese, G. Correale, M. Manfra, et al., Thiazolidin-4-one formation. Mechanistic and synthetic aspects of the reaction of imines and mercaptoacetic acid under microwave and conventional heating, Org. Biomol. Chem. 2 (2004) 2809-2813.
1. [1]
  Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995
2. [2]
  Jing LIANG , Qian WANG , Junfeng BAI . Synthesis and structures of cdq-topological quaternary and (4, 4, 8)-c topological quinary Zn-MOFs with both oxalic acid and triazole ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2186-2192. doi: 10.11862/CJIC.20240177
3. [3]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
4. [4]
  Xun Zhu , Chenchen Zhang , Yingying Li , Yin Lu , Na Huang , Dawei Wang . Degradation of perfluorooctanoic acid by inductively heated Fenton-like process over the Fe₃O₄/MIL-101 composite. Chinese Chemical Letters, 2024, 35(12): 109753-. doi: 10.1016/j.cclet.2024.109753
5. [5]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
6. [6]
  Huipeng Zhao , Xiaoqiang Du . Polyoxometalates as the redox anolyte for efficient conversion of biomass to formic acid. Chinese Journal of Structural Chemistry, 2024, 43(2): 100246-100246. doi: 10.1016/j.cjsc.2024.100246
7. [7]
  Dan-Ying Xing , Xiao-Dan Zhao , Chuan-Shu He , Bo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436
8. [8]
  Lihang Wang , Mary Li Javier , Chunshan Luo , Tingsheng Lu , Shudan Yao , Bing Qiu , Yun Wang , Yunfeng Lin . Research advances of tetrahedral framework nucleic acid-based systems in biomedicine. Chinese Chemical Letters, 2024, 35(11): 109591-. doi: 10.1016/j.cclet.2024.109591
9. [9]
  Hanqing Zhang , Xiaoxia Wang , Chen Chen , Xianfeng Yang , Chungli Dong , Yucheng Huang , Xiaoliang Zhao , Dongjiang Yang . Selective CO2-to-formic acid electrochemical conversion by modulating electronic environment of copper phthalocyanine with defective graphene. Chinese Journal of Structural Chemistry, 2023, 42(10): 100089-100089. doi: 10.1016/j.cjsc.2023.100089
10. [10]
  Linshan Peng , Qihang Peng , Tianxiang Jin , Zhirong Liu , Yong Qian . Highly efficient capture of thorium ion by citric acid-modified chitosan gels from aqueous solution. Chinese Chemical Letters, 2024, 35(5): 108891-. doi: 10.1016/j.cclet.2023.108891
11. [11]
  Yingying Yan , Wanhe Jia , Rui Cai , Chun Liu . An AIPE-active fluorinated cationic Pt(Ⅱ) complex for efficient detection of picric acid in aqueous media. Chinese Chemical Letters, 2024, 35(5): 108819-. doi: 10.1016/j.cclet.2023.108819
12. [12]
  Fengyun Li , Zerong Pei , Shuting Chen , Gen li , Mengyang Liu , Liqin Ding , Jingbo Liu , Feng Qiu . Multifunctional nano-herb based on tumor microenvironment for enhanced tumor therapy of gambogic acid. Chinese Chemical Letters, 2024, 35(5): 108752-. doi: 10.1016/j.cclet.2023.108752
13. [13]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
14. [14]
  Peizhe Li , Qiaoling Liu , Mengyu Pei , Yuci Gan , Yan Gong , Chuchen Gong , Pei Wang , Mingsong Wang , Xiansong Wang , Da-Peng Yang , Bo Liang , Guangyu Ji . Chlorogenic acid supported strontium polyphenol networks ensemble microneedle patch to promote diabetic wound healing. Chinese Chemical Letters, 2024, 35(8): 109457-. doi: 10.1016/j.cclet.2023.109457
15. [15]
  Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
16. [16]
  Shiyu Pan , Bo Cao , Deling Yuan , Tifeng Jiao , Qingrui Zhang , Shoufeng Tang . Complexes of cupric ion and tartaric acid enhanced calcium peroxide Fenton-like reaction for metronidazole degradation. Chinese Chemical Letters, 2024, 35(7): 109185-. doi: 10.1016/j.cclet.2023.109185
17. [17]
  Xubin Qian , Lei Xu , Xu Ge , Zhun Liu , Cheng Fang , Jianbing Wang , Junfeng Niu . Can perfluorooctanoic acid be effectively degraded using β-PbO₂ reactive electrochemical membrane?. Chinese Chemical Letters, 2024, 35(7): 109218-. doi: 10.1016/j.cclet.2023.109218
18. [18]
  Xinyue Lan , Junguang Liang , Churan Wen , Xiaolong Quan , Huimin Lin , Qinqin Xu , Peixian Chen , Guangyu Yao , Dan Zhou , Meng Yu . Photo-manipulated polyunsaturated fatty acid-doped liposomal hydrogel for flexible photoimmunotherapy. Chinese Chemical Letters, 2024, 35(4): 108616-. doi: 10.1016/j.cclet.2023.108616
19. [19]
  Dexuan Xiao , Tianyu Chen , Tianxu Zhang , Sirong Shi , Mei Zhang , Xin Qin , Yunkun Liu , Longjiang Li , Yunfeng Lin . Transdermal treatment for malignant melanoma by aptamer-modified tetrahedral framework nucleic acid delivery of vemurafenib. Chinese Chemical Letters, 2024, 35(4): 108602-. doi: 10.1016/j.cclet.2023.108602
20. [20]
  Yiqiao Chen , Ao Liu , Biwen Yang , Zhenzhen Li , Binggang Ye , Zhouyi Guo , Zhiming Liu , Haolin Chen . Photoluminescence and photothermal conversion in boric acid derived carbon dots for targeted microbial theranostics. Chinese Chemical Letters, 2024, 35(9): 109295-. doi: 10.1016/j.cclet.2023.109295

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(616)
HTML views(20)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

One-pot synthesis of 1, 3-thiazolidin-4-one using Bi(SCH2COOH)3 as catalyst

Metrics

通讯作者: 陈斌, bchen63@163.com

One-pot synthesis of 1, 3-thiazolidin-4-one using Bi(SCH₂COOH)₃ as catalyst