Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2020; 52(17): 2541-2550
DOI: 10.1055/s-0040-1707120
DOI: 10.1055/s-0040-1707120
paper
Sulfite-Promoted C–H Fluoroalkyl Sulfuration of Imidazoheterocycles with Bromofluoroacetate and Elemental Sulfur
We gratefully thank the Guangdong Basic and Applied Basic Research Foundation (Grant No. 2019B151502052) for financial support.
Further Information
Publication History
Received: 05 March 2020
Accepted after revision: 22 April 2020
Publication Date:
18 May 2020 (online)
Abstract
A transition-metal-free sulfite-promoted three-component C–H sulfuration between imidazoheterocycles, elemental sulfur, and bromofluoroacetate is developed. Sulfites, including Na2S2O4, NaHSO3, and Na2S2O3, are able to promote the formation of two C–S bonds in one step using elemental sulfur as a green sulfurating agent, allowing the rapid introduction of the synthetically useful S-fluoroacetate group into imidazoheterocycles. These new imidazoheterocycle derivatives bearing an S-fluoroacetate group can be easily modified to produce pharmaceutically attractive compounds.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707120.
- Supporting Information
-
References
- 1a Mellah M, Voituriez A, Schulz E. Chem. Rev. 2007; 107: 5133
- 1b Landelle G, Panossian A, Leroux FR. Curr. Top. Med. Chem. 2014; 14: 941
- 1c Feng M, Tang B, Liang SH, Jiang X. Curr. Top. Med. Chem. 2016; 16: 1200
- 1d Zhao J, Jiang X. Chin. Chem. Lett. 2018; 29: 1079
- 1e Wang N, Saidhareddy P, Jiang X. Nat. Prod. Rep. 2020; 37: 246
- 2a Jarrett JT. J. Biol. Chem. 2015; 290: 3972
- 2b Konaklieva MI, Plotkin BJ. Recent Pat. Anti-Infect. Drug Discovery 2006; 1: 177
- 2c Zysman-Colman E, Leste-Lassere P, Harpp DN. J. Sulfur Chem. 2008; 29: 309
- 3a Ghaderi A. Tetrahedron 2016; 72: 4758 ; and references cited therein
- 3b Qiao Z, Jiang X. Org. Biomol. Chem. 2017; 15: 1942
- 3c Shen C, Zhang P, Sun Q, Bai S, Hor TS. A, Liu X. Chem. Soc. Rev. 2015; 44: 291
- 4a Nguyen BT. Adv. Synth. Catal. 2017; 359: 1066 ; and references cited therein
- 4b Meyer B. Chem. Rev. 1976; 76: 367
- 5a Chen F.-J, Liao G, Li X, Wu J, Shi B.-F. Org. Lett. 2014; 16: 5644
- 5b Han R, Hillhouse GL. J. Am. Chem. Soc. 1998; 120: 7657
- 5c Chen C, Chu L, Qing F.-L. J. Am. Chem. Soc. 2012; 134: 12454
- 5d Zhou Z, Liu Y, Chen J, Yao E, Cheng J. Org. Lett. 2016; 18: 5268
- 5e Chen C, Xie Y, Chu L, Wang R.-W, Zhang X, Qing F.-L. Angew. Chem. Int. Ed. 2012; 51: 2492
- 5f Shibahara F, Kanai T, Yamaguchi E, Kamei A, Yamauchi T, Murai T. Chem. Asian J. 2014; 9: 237
- 5g Zhang G, Yi H, Chen H, Bian C, Liu C, Lei A. Org. Lett. 2014; 16: 6156
- 5h Wang Z, Wang Y, Zhang W.-X, Hou Z, Xi Z. J. Am. Chem. Soc. 2009; 131: 15108
- 5i Nguyen TB, Ermolenko L, Al-Mourabit A. Org. Lett. 2013; 15: 4218
- 5j Wang M, Fan Q, Jiang X. Org. Lett. 2016; 18: 5756
- 5k Feng C, Peng Y, Ding G, Li X, Cui C, Yan Y. Chem. Commun. 2018; 54: 13367
- 5l Liu Z, Gao R, Lou J, He Y, Yu Z. Adv. Synth. Catal. 2018; 360: 3097
- 6a Siva Reddy A, Kumara Swamy KC. Org. Lett. 2015; 17: 2996
- 6b Arisawa M, Ichikawa T, Yamaguchi M. Org. Lett. 2012; 14: 5318
- 6c Huang Y, He X, Lin X, Rong M, Weng Z. Org. Lett. 2014; 16: 3284
- 6d Weng Z, He W, Chen C, Lee R, Tan D, Lai Z, Kong D, Yuan Y, Huang K.-W. Angew. Chem. Int. Ed. 2013; 52: 1548
- 6e Paul R, Punniyamurthy T. RSC Adv. 2012; 2: 7057
- 6f Xiao F, Chen S, Li C, Huang H, Deng G.-J. Adv. Synth. Catal. 2016; 358: 3881
- 7a Liao Y, Peng Y, Qi H, Deng G.-J, Gong H, Li C.-J. Chem. Commun. 2015; 51: 1031
- 7b Liu J, Yan X, Liu N, Zhang Y, Zhao S, Wang X, Zhuo K, Yue Y. Org. Chem. Front. 2018; 5: 1034
- 7c Liu J, Zhang Y, Yue Y, Wang Z, Shao H, Zhuo K, Lv Q, Zhang Z. J. Org. Chem. 2019; 84: 12946
- 7d Lu C, Huang H, Tuo X, Jiang P, Zhang F, Deng G.-J. Org. Chem. Front. 2019; 6: 2738
- 7e Thomas J, Jana S, Sonawane M, Fiey B, Balzarini J, Liekens S, Dehaen W. Org. Biomol. Chem. 2017; 15: 3892
- 8a Li J, Li C, Yang S, An Y, Wu W, Jiang H. J. Org. Chem. 2016; 81: 7771
- 8b Ravi C, Reddy NN. K, Pappula V, Samanta S, Adimurthy S. J. Org. Chem. 2016; 81: 9964
- 8c Shi S, Chen J, Zhuo S, Wu Z, Fang M, Tang G, Zhao Y. Adv. Synth. Catal. 2019; 361: 3210
- 8d Wu W, Ding Y, Xie P, Tang Q, Pittman CU. Jr, Zhou A. Tetrahedron 2017; 73: 2151
- 8e Zhu W, Ding Y, Bian Z, Xie P, Xu B, Tang Q, Wu W, Zhou A. Adv. Synth. Catal. 2017; 359: 2215
- 9a Zhang J.-R, Liao Y.-Y, Deng J.-C, Feng K.-Y, Zhang M, Ning Y.-Y, Lin Z.-W, Tang R.-Y. Chem. Commun. 2017; 53: 7784
- 9b Zhang J.-R, Zhan L.-Z, Wei L, Ning Y.-Y, Zhong X.-L, Lai J.-X, Xu L, Tang R.-Y. Adv. Synth. Catal. 2018; 360: 533
- 9c Gao Y.-C, Huang Z.-B, Xu L, Li Z.-D, Lai Z.-S, Tang R.-Y. Org. Biomol. Chem. 2019; 17: 2279
- 9d Deng J.-C, Zhang J.-C, Li M.-H, Huang J.-C, Lai Z.-S, Tong X.-Y, Cui Z.-N, Tang R.-Y. Org. Biomol. Chem. 2019; 17: 7854
- 9e Deng J.-C, Zhuang S.-B, Liu Q.-Z, Lin Z.-W, Su Y.-L, Chen J.-H, Tang R.-Y. RSC Adv. 2017; 7: 54013
- 10a Enguehard-Gueiffier C, Gueiffier A. Mini-Rev. Med. Chem. 2007; 7: 888
- 10b Couty F, Evano G. In Comprehensive Heterocyclic Chemistry III, Vol. 11. Katritzky AR, Rees CW. Pergamon; Oxford: 2008: 409
- 10c Koubachi J, Kazzouli SE, Bousmina M, Guillaumet G. Eur. J. Org. Chem. 2014; 5119 ; and references cited therein
- 11 Ilardi EA, Vitaku E, Njardarson JT. J. Med. Chem. 2014; 57: 2832
- 12a Deng J.-C, Gao Y.-C, Zhu Z, Xu L, Li Z.-D, Tang R.-Y. Org. Lett. 2019; 21: 545
- 12b Deng J.-C, Chen J.-H, Zhang J.-R, Lu T.-T, Tang R.-Y. Adv. Synth. Catal. 2018; 360: 4795
- 13a Jiao J, Wei L, Ji X.-M, Hu M.-L, Tang R.-Y. Adv. Synth. Catal. 2016; 358: 268
- 13b Wei L, Deng J.-C, Zhuo B.-L, Xu L, Tang R.-Y. ChemistrySelect 2016; 1: 6293
- 13c Wei L, Xu L, Tang R.-Y. RSC Adv. 2015; 5: 107927
- 13d Ji X.-M, Zhu S.-J, Chen F, Zhang X.-G, Tang R.-Y. Synthesis 2015; 47: 659
- 13e Huang Z.-H, Xia X.-J, Huang Z.-H, Xu L, Zhang X.-Y, Tang R.-Y. Org. Biomol. Chem. 2020; 18: 1369
- 14a Xiao X, Feng M, Jiang X. Chem. Commun. 2015; 51: 4208
- 14b Zhang Y, Li Y, Zhang X, Jiang X. Chem. Commun. 2015; 51: 941
- 15 Douha A, Amat-Guerri F, Acuna AU. J. Phys. Chem. 1995; 99: 76
- 16a Kazzouli SE, Bellay AG, Berteina-Raboin S, Delagrange P, Caignard D.-H, Guillaumet G. Eur. J. Med. Chem. 2011; 46: 4252
- 16b Trapani G, Franco M, Ricciardi L, Latrofa A, Genchi G, Sanna E, Tuveri F, Cagetti E, Biggio G, Liso G. J. Med. Chem. 1997; 40: 3109
- 17a Zhang C.-P, Chen Q.-Y, Guo Y, Xiao J.-C, Gu Y.-C. Chem. Soc. Rev. 2012; 41: 4536
- 17b Huang B.-N, Huang W.-Y, Hu C.-M. Acta Chim. Sinica 1981; 39: 481
- 18a Fu W, Song Q. Org. Lett. 2018; 20: 393
- 18b Ouyang X.-H, Song R.-J, Li J.-H. Chem. Asian J. 2018; 13: 2316
- 18c Chen J.-H, Wasim A, Li M.-H, Li Z.-D, Cui Z.-N, Tang R.-Y. Adv. Synth. Catal. 2020; 362: 269
For reviews on the construction of C–S bonds, see:
For recent references on the sulfuration of indoles using elemental sulfur, see:
For recent references on the sulfuration of imidazoheterocycles using elemental sulfur, see:
For our publications on the sulfuration of imidazoheterocycles using elemental sulfur, see: