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 2021; 53(10): 1795-1804
DOI: 10.1055/a-1343-9451
DOI: 10.1055/a-1343-9451
paper
Straightforward Route to γ-Sultams via Novel Tandem SN/Michael Addition
This research was supported by the grant of the President of the Russian Federation project no. МK-1073.2020.3.
Abstract
A novel tandem approach to trisubstituted γ-sultams has been developed involving N-alkylation of methanesulfonanilides with EWG-substituted allyl bromides followed by intramolecular Michael addition. A series of various isothiazolidine 1,1-dioxides have been prepared under mild transition-metal-free conditions in high yields and trans-diastereoselectivity (confirmed by X-ray crystallography). The dependence of reactivity on electronic properties of substrates has been investigated.
Keywords
sultam - isothiazolidine - tandem - nucleophilic substitution - Michael addition - cyclic sulfonamide - allyl bromide - stereoselectiveSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1343-9451. Crystallographic data and copies of NMR spectra are included.
- Supporting Information
Publication History
Received: 04 November 2020
Accepted after revision: 29 December 2020
Accepted Manuscript online:
29 December 2020
Article published online:
25 January 2021
© 2020. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 www.drugbank.com.
- 2a Jin H, Wright M, Pastor R, Mish M, Metobo S, Jabri S, Lansdown R, Cai R, Pyun P, Tsiang M, Chen X, Kim CU. Bioorg. Med. Chem. Lett. 2008; 18: 1388
- 2b Brzozowski Z, Saczewski F, Neamati N. Bioorg. Med. Chem. Lett. 2006; 16: 5298
- 3 Koeplinger KA, Zhao Z, Peterson T, Leone JW, Schwende FS, Heinrikson RL, Tomasselli AG. Drug Metabol. Disp. 1999; 27: 986
- 4 Valente C, Guedes RC, Moreira R, Iley J, Gut J, Rosenthal PJ. Bioorg. Med. Chem. Lett. 2006; 16: 4115
- 5 Wroblewski T, Graul A, Castañer J. Drugs Fut. 1998; 23: 365
- 6 Hansen JM, Kristensen M, Skovsted L. Epilepsia 1968; 9: 17
- 7 Hanessian S, Sailes H, Therrien E. Tetrahedron 2003; 59: 7047
- 8 Koeplinger KA, Zhao Z, Peterson T, Leone JW, Schwende FS, Heinrikson RL, Tomasselli AG. Drug Metab. Dispos. 1999; 27: 986
- 9 Oppolzer W. Pure Appl. Chem. 1990; 62: 1241
- 10a Dibchak D, Shcherbacova V, Denisenko AV, Mykhailiuk PK. Org. Lett. 2019; 21: 8909
- 10b Greig IR, Tozer MJ, Wright PT. Org. Lett. 2001; 3: 369
- 10c Chiacchio U, Corsaro A, Rescifina A, Bkaithan M, Grassi G, Piperno A, Privetera T, Romeo G. Tetrahedron 2001; 57: 3425
- 10d Plietker B, Seng D, Fröhlich R, Metz P. Tetrahedron 2000; 56: 873
- 11a Rassadin VA, Grosheva DS, Arefeva IA, Tomashevskiy AA, Sokolov VV, de Meijere A. Eur. J. Org. Chem. 2012; 5028
- 11b Rassadin VA, Tomashevskiy AA, Sokolov VV, Ringe A, Magull J, de Meijere A. Eur. J. Org. Chem. 2009; 2635
- 11c Rassadin VA, Grosheva DS, Tomashevskiy AA, Sokolov VV, Yufit DS, Kozhushkov SI, de Meijere A. Eur. J. Org. Chem. 2010; 3481
- 11d Enders D, Moll A, Bats JW. Eur. J. Org. Chem. 2006; 1271
- 12a Bressy C, Menant C, Piva O. Synlett 2005; 57
- 12b Hanessian S, Sailes H, Therrien E. Tetrahedron 2003; 59: 7047
- 13a Zhong D, Wu D, Zhang Y, Lu Z, Usman M, Liu W, Lu X, Liu WB. Org. Lett. 2019; 21: 5808
- 13b Yang Z, Xu J. Chem. Commun. 2014; 50: 3616
- 13c Li X, Hu X, Liu Z, Yang J, Mei B, Dong Y, Liu G. J. Org. Chem. 2020; 85: 5916
- 14a Rolfe A, Young K, Hanson PR. Eur. J. Org. Chem. 2008; 5254
- 14b Joardar S, Das S, Chakravorty S. Synlett 2014; 26: 359
- 15a Leit SM, Paquette LA. J. Org. Chem. 1999; 64: 9225
- 15b Biswas D, Samp L, Ganguly AK. Tetrahedron Lett. 2010; 51: 2681
- 16 Yan J, Cheo HW, Teo WK, Shi X, Wu H, Idres SB, Deng LW, Wu J. J. Am. Chem. Soc. 2020; 142: 11357
- 17a Pan Z, Wang S, Brethorst JT, Douglas CJ. J. Am. Chem. Soc. 2018; 140: 3331
- 17b Song B, Yu CB, Ji Y, Chen MW, Zhou YG. Chem. Commun. 2017; 53: 1704
- 17c Tao Y, Gilbertson SR. Chem. Commun. 2018; 54: 11292
- 18a Lebegue N, Flouquet N, Berthelot P, Pfeiffer B, Renard P. Synth.Commun. 2002; 32: 2877
- 18b Gilleron P, Wlodarczyk N, Houssin R, Farce A, Laconde G, Goossens J.-F, Lemoine A, Pommery N, Henichart J.-P, Millet R. Bioorg. Med. Chem. Lett. 2007; 17: 5465
- 19a Zang Q, Javed S, Hill D, Ullah F, Bi D, Porubsky P, Neuenswander B, Lushington GH, Santini C, Organ MG, Hanson PR. ACS Comb. Sci. 2012; 14: 456
- 19b Rolfe A, Samarakoon TB, Hanson PR. Org. Lett. 2010; 12: 1216
- 20 Grosheva DS, Rassadin VA, Sokolov VV. Eur. J. Org. Chem. 2015; 1355
- 21 CCDC 2036644 (3e) and CCDC 2036645 (3r) contain 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.