Effective and Catalyst-Free Preparation of Thiazolidines via Novel [3+2] Annulation of 1,4-Dithiane-2,5-diol and Benzothiazolimines

Abstract

A novel [3+2] annulation of 1,4-dithiane-2,5-diol and benzothiazolimines has been developed for the efficient, one-step preparation of highly sterically demanding thiazolidines in excellent yields (up to 99%) and moderate diastereoselectivities (1:1 to 2.4:1) under mild conditions within a few minutes. A series of thiazolidines compounds were obtained and a scaled-up experiment was conducted with excellent results. The absorption, metabolism, and toxic (ADMET) properties of the compounds were evaluated with good results, demonstrating the potential applications of this protocol.

Key words

[3+2] annulation - 1,4-dithiane-2,5-diol - benzothiazolimines - thiazolidines - ADMET

• References and Notes


For selected reviews, see:
• 1a Venkatesh P, Pandeya NS. Int. J. ChemTech Res. 2009; 1: 1354
• 1b Liu Y, Wang Y, Dong G, Zhang Y, Wu S, Miao Z, Yao J, Zhang W, Sheng C. MedChemComm 2013; 4: 1551
• 1c Delmas F, Avellaneda A, Giorgio DC, Robin M, De Clercq E, Timon-David P, Galy J.-P. Eur. J. Med. Chem. 2004; 39: 685
• 1d Munirajasekhar D, Himaja M, Sunil VM. Int. Res. J. Pharm. 2011; 2: 114
• 1e Siddiqui N, Rana A, Khan AS, Bhat MA, Haque SE. Bioorg. Med. Chem. Lett. 2007; 17: 4178

For reviews, see:
• 2a Base JY, Caldwell RD, Caravella JA, Chen L, Creech KL, Deaton DN, Madauss KP, Marr HB, McFadyen RB, Miller AB, Parks DJ, Todd D, Williams SP, Wisely GB. Bioorg. Med. Chem. Lett. 2009; 19: 2969
• 2b Sakai J, Miura I, Shibata M, Yonekura N, Hiyoshi H, Takagaki M, Nagayama K. J. Pestic. Sci. 2010; 35: 488
• 2c Jin LH, Song BA, Zhang GP, Xu RQ, Zhang SM, Gao XW, Hu DY, Yang S. Bioorg. Med. Chem. Lett. 2006; 16: 1537
• 2d Amnerkar ND, Bhusari KP. Eur. J. Med. Chem. 2010; 45: 149
• 2e Jaiswal S, Mishra PA, Srivastava A. Res. J. Pharm. Biol. Chem. Sci. 2012; 3: 631
• 3a Blacker AJ, Farah MM, Hall ML, Marsden SP, Saidi O, Williams JM. J. Org. Lett. 2009; 11: 2039
• 3b Parikh N, Kumar D, Roya SR, Chakraborti AK. Chem. Commun. 2011; 47: 1797
• 3c Liao Y.-F, Qi H.-R, Chen S.-P, Jiang P, Zhou W, Deng G.-J. Org. Lett. 2012; 14: 6004
• 4a Cheng YY, Peng Q, Fan WG, Li PX. J. Org. Chem. 2014; 79: 5812
• 4b Laurie LJ, Robert AB. Org. Lett. 2009; 11: 2792
• 4c Wu D, Zhang X, Xu Y, Xue Y, Li J, Wang W, Zhu J. Asian J. Org. Chem. 2014; 3: 480
• 5a Chen XL, Li X, Qu LB, Tang Y.-C, Mai W.-P, Wei D.-H, Bi W.-Z, Duan L.-K, Sun K, Chen J.-Y, Ke D.-D, Zhao Y.-F. J. Org. Chem. 2014; 79: 8407
• 5b Song XX, Gu MJ, Chen XJ, Xu L, Ni QJ. Asian J. Org. Chem. 2019; 8: 2180
• 5c Lu D.-M, Wu JH, Pan J.-K, Chen X, Ren XY, Tian L, Wang TL. Chem. Commun. 2020; 56: 11231
• 5d Zhang Y, Yang JH, Xia YQ, Dong L, Chen FE. Chem. Eur. J. 2021; 27: 6183
• 6a Keri SR, Patil RM, Patil AS, Budagumpi S. Eur. J. Med. Chem. 2015; 89: 207
• 6b Kumbhare RM, Kosurkar UB, Ramaiah MJ, Dadmal TL, Pushpavalli SN. C. V. L, Pal-Bhadra M. Bioorg. Med. Chem. Lett. 2012; 22: 5424
• 6c Zhang P, Pan S, Chen W, Liu M, Wu H. J. Org. Chem. 2018; 83: 3354
• 7a Yu JC, Yu LM, Zhao XY, Gan L, Zhu W.-w, Wang Z.-c, Wang R, Jiang X. Org. Chem. Front. 2018; 5: 2040
• 7b Shi WJ, Sun SF, Hu YM, Gao T, Peng Y, Wu M, Guo H, Wang J. Tetrahedron Lett. 2015; 56: 3861
• 7c Cheng P, Guo WG, Chen P, Liu Y, Du X, Li C. Chem. Commun. 2016; 52: 3418
• 7d Prasad MS, Bharani S, Sivaprakash M, Vadivelu P, Kumar DS. S, Chowhan LR. Org. Biomol. Chem. 2023; 21: 4972
• 8a Varshnaya RK, Banerjee P. Org. Biomol. Chem. 2017; 15: 5182
• 8b He ZL, Chen Y, Wang XH, Ni MW, Wang G. Tetrahedron 2019; 75: 130461
• 8c Wan XY, Li HW, Wang S, Wang CD. J. Org. Chem. 2022; 87: 13375
• 8d Hui YH, Li JP, Yu B, Xing X, Gao T, Qian X, Zhang Y, Chen W. New J. Chem. 2022; 46: 6804
• 9a Li H, Zu L.-S, Xie H.-X, Wang J, Jiang W, Wang W. Org. Lett. 2007; 9: 1833
• 9b Yu C, Zhang Y, Song A, Ji Y, Wang W. Chem. Eur. J. 2011; 17: 770
• 9c Meninno S, Croce G, Lattanzi A. Org. Lett. 2013; 15: 3436
• 10a Zhao BL, Liu L, Du DM. Eur. J. Org. Chem. 2014; 7850
• 10b Duan SW, Li Y, Liu YY, Zou YQ, Shi DQ, Xiao WJ. Chem. Commun. 2012; 48: 5160
• 10c Mahajan S, Chauhan P, Blümel M, Puttreddy R, Rissanen K, Raabe G, Enders D. Synthesis 2016; 48: 1131
• 10d Zhu XY, Lv MH, Zhao YN, Lan LY, Li WZ, Xiao LJ. RSC Adv. 2018; 8: 34000
• 11 CCDC 2306452 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures