A Facile and Efﬁcient Approach for the Synthesis of 3-Aryl-4-hydroxy-1,3-thiazolidin-2-onesThis project was supported by Natural Science Foundation of Zhejiang Province (Grant No. LY16H300001) to G. Zhang and National Natural Science Foundation of China (Grant No. 81673291 and 81473074) and Osteoporosis & Breast Cancer Research Center, U.S.A. to Y. Yu.
Received: 04 November 2018
Accepted after revision: 01 February 2019
01 April 2019 (eFirst)
§ Yue Zhu and Qilin Wang contributed equally to this work.
A facile and efficient method for the synthesis of 3-aryl-4-hydroxy-1,3-thiazolidin-2-ones by the reaction of 1,4-dithiane-2,5-diol with acyl azides is reported. This reaction proceeded well at 80 °C to afford products in excellent yields for a wide range of substrates. A possible mechanism has been proposed.
Key words3-aryl-4-hydroxy-1,3-thiazolidin-2-ones - 1,4-dithiane-2,5-diol - acyl azide - nucleophilic addition - facile synthesis
- 1 Kenda B, Turet L, Quesnel L, Michel P. Patent PCT Int. Appl. 2008132139, 2008
- 2 Albers HM. H. G, Hendrickxt LJ. D, van Tol RJ. P, Hausmann J, Perrakis A, Ovaa H. J. Med. Chem. 2011; 54: 4619
- 3 Sartori E, Teulon J.-M. U.S. Patent 5859036, 1999
- 4 Hamersma JA. M, Speckamp WN. Tetrahedron 1982; 38: 3255
- 5 Minville J, Girardin M, Spino C. Can. J. Chem. 2007; 85: 603
- 6 Gouhar RS, Kamel MM. J. Heterocycl. Chem. 2018; 55: 2082
- 7a Kumar SV, Muthusubramanian S, Perumal S. RSC Adv. 2015; 5: 90451
- 7b Zhou H, Hong J, Huang J, Chen Z. Asian J. Org. Chem. 2017; 6: 817
- 8a Zhou H, Hong J, Huang J. Asian J. Org. Chem. 2017; 6: 817
- 8b Dengiz Ç, Balci M. Turk. J. Chem. 2013; 37: 220
- 9 Sanphanya K, Wattanapitayakul SK, Prangsaengtong O. Bioorg. Med. Chem. Lett. 2012; 22: 3001