Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 10
152
Views
1
CrossRef citations to date
0
Altmetric
SYNTHETIC COMMUNICATIONS REVIEWS

An efficient one-pot strategy for the synthesis of 4- methylene-2-thiazolidinethiones in water

, , , &
Pages 1561-1566 | Received 17 Sep 2019, Published online: 02 Apr 2020

References

  • Rufino, A. R.; Biaggio, F. C. Synthesis of a Novel Prostaglandin Containing Heteroatoms in the Ring Cyclopentane. Tetrahedron Lett. 2001, 42, 8559–8561. DOI: 10.1016/S0040-4039(01)01861-5.
  • Biaggio, F. C.; Rufino, A. R.; Silveira, M. C. F. Synthesis of Novel Heterocyclic Prostaglandin Analogues. Lett. Org. Chem. 2007, 4, 1–3. DOI: 10.2174/157017807780037388.
  • Wang, J.; Liu, H.-B.; Wang, W.; Kim, I.; Ha, C.-S. A Thiazoline-Containing Cobalt (II) Complex Based Colorimetric Fluorescent Probe: “Turn-on” Detection of Fluoride. Dalton Trans. 2009, 104, 10422–10425. DOI: 10.1039/b918887h.
  • Farina, V.; Reeves, J. T.; Senanayake, C. H.; Song, J. J. Asymmetric Synthesis of Active Pharmaceutical Ingredients. Chem. Rev. 2006, 106, 2734–2793. DOI: 10.1021/cr040700c.
  • Baiget, J.; Cosp, A.; Gálvez, E.; Gómez-Pinal, L.; Romea, P.; Urpí, F. On the Influence of Chiral Auxiliaries in the Stereoselective Cross-Coupling Reactions of Titanium Enolates and Acetals. Tetrahedron 2008, 64, 5637–5633. DOI: 10.1016/j.tet.2008.04.044.
  • Hwu, J. R.; Hsu, Y. C. Stereospecific Benzyne-Induced Olefination from β-Amino Alcohols and Its Application to Thetotal Synthesis of (–)-1-deoxy-D-Fructose. Chem. Eur. J. 2011, 17, 4727–4731. DOI: 10.1002/chin.201133038.
  • Tungen, J. E.; Aursnes, M.; Hansen, T. V. Stereoselective Synthesis of Maresin 1. Tetrahedron Lett. 2015, 56, 1843–1846. DOI: 10.1016/j.tetlet.2015.02.080.
  • Delaunay, D.; Toupet, L.; Le Corre, M. Reactivity of β-Amino Alcohols with Carbon Disulfide. Study on the Synthesis of 2-Oxazolidinethiones and 2-Thiazolidinethiones. J. Org. Chem. 1995, 60, 6604–6607. DOI: 10.1002/chin.199609139.
  • Chen, N.; Jia, W.-Y.; Xu, J.-X. A Versatile Synthesis of Various Substituted Taurines from Vicinal Amino Alcohols and Aziridines. Eur. J. Org. Chem. 2009, 2009, 5841–5846. DOI: 10.1002/ejoc.200900759.
  • Lu, Z.; Yang, Y.-Q.; Xiong, W.-X. Preparation of 1,3-Thiazolidine-2-Thiones by Using Potassium Ethylxanthate as a Carbon Disulfide Surrogate. Synlett. 2019, 30, 713–716. DOI: 10.1055/s-0037-1612124.
  • Shi, M.; Shen, Y.-M. Transition-Metal-Catalyzed Reactions of Propargylamine with Carbon Dioxide and Carbon Disulfide. J. Org. Chem. 2002, 67, 16–21. DOI: 10.1021/jo0014966.
  • Liu, A. H.; He, L. N.; Peng, S. Y.; Pan, Z. D.; Wang, J. L.; Gao, J. Environmentally Benign Chemical Fixation of CO2 Catalyzed by the Functionalized Ion-Exchange Resins. Sci. China Chem. 2010, 53, 1578–1585. DOI: 10.1007/s11426-010-4028-6.
  • Nasiri, F.; Zolali, A.; Ahmadiazar, M. A Convenient Solvent-Free and One-Pot Synthesis of 4-Hydroxythiazolidine-2-Thiones. J. Sulfur. Chem. 2014, 35, 412–417. DOI: 10.1080/17415993.2014.907407.
  • Ziyaei-Halimehjani, A.; Marjani, K.; Ashouri, A. A One-Pot, Three-Component Synthesis of Thiazolidine-2-Thiones. Tetrahedron Lett. 2012, 53, 3490–3492. DOI: 10.1016/j.tetlet.2012.04.129.
  • Safa, K. D.; Alyari, M. Synthesis of Thioalkyne-Substituted Thiazolidine-2-Thiones Using Tris(Trimethylsilyl)Methyllithium and Carbon Disulfide. Synthesis 2014, 47, 256–262. DOI: 10.1055/s-0034-1379253.
  • Nechaev, A. A.; Peshkov, A. A.; Hecke, K. V.; Peshkov, V. A.; Van der Eycken, E. V. Synthesis of Thiazolidine-2-Thiones through a One-Pot A-Coupling-Carbon Disulfide Incorporation Process. Eur. J. Org. Chem. 2017, 2017, 1063–1069. DOI: 10.1002/ejoc.201601103.
  • Weng, H.-Q.; Yue, B.-J.; Xu, M.; Yang, Y.-K.; Jin, H.-W. Switchable Copper-Catalyzed Cascade Synthesis of Thiazolidine-2-Thiones and Thiazole-2(3H)-Thiones. Synthesis 2015, 47, 2991–2996. DOI: 10.1055/s-0034-1380815.
  • Anitha, M.; Kumara Swamy, K. C. Synthesis of Thiazolidine-Thiones, Imino-Thiazolidines and Oxazolidines via the Base Promoted Cyclisation of Epoxy-Sulfonamides and Heterocumulenes. Org. Biomol. Chem. 2018, 16, 402–413. DOI: 10.1039/C7OB02915B.
  • Jacobine, A. M.; Posner, G. H. Three-Component, One-Flask Synthesis of Rhodanines (Thiazolidinones). J. Org. Chem. 2011, 76, 8121–8125. DOI: 10.1021/jo201561t.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.