Synthesis, Table of Contents Synthesis 2023; 55(03): 489-498DOI: 10.1055/a-1944-2423 paper One-Pot, Base- and Metal-Free Practical Synthesis of Novel Cycloalkene-Fused [1,4]Thiazepines through the Sequential Ugi/SNCsp2 Reactions Authors Ahmad Takallou Sulaiman Al-Shidhani Muhammad U. Anwar Ahmed Al-Harrasi∗ Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract A one-pot and sequential Ugi/SNCsp2 four-component reaction was introduced for the synthesis of cycloalkene-fused [1,4]thiazepine derivatives. A variety of cyclic β-bromovinyl aldehyde with different sizes, amines, and isocyanides were reacted with thioglycolic acid. This approach can provide a practical and rapid access to the fused bioactive cycloalkene structures containing thiazepine, and peptide unit, which proved the achievement of a significant structural diversity. Further use of this method has been successfully applied in synthesizing a variety of quinoline-fused [1,4]thiazepines with satisfactory results. The practical nature of this approach was demonstrated by a gram-scale synthesis of a selected product. Key words Key wordsthiazepines - sequential reactions - Ugi reaction - fused heterocycles - β-bromovinyl aldehyde Full Text References References 1a Bauer A, Borsos E, Maulide N. Eur. J. Org. Chem. 2020; 3971 1b Liu A, Guo T, Zhang S, Yang H, Zhang Q, Chai Y, Zhang S. Org. Lett. 2021; 23: 6326 1c Chen J, Jia P, Huang Y. Org. Lett. 2018; 20: 6715 1d Dong Z, Liu C-H, Wang Y, Lin M, Yu ZX. Angew. Chem. Int. Ed. 2013; 52: 14157 1e Prie G, Prevost N, Twin H, Fernandes SA, Hayes JF, Shipman MA. Angew. Chem. Int. Ed. 2003; 43: 6517 2a Reutskaya E, Sapegin A, Peintner S, Erdélyi M, Krasavin M. J. Org. Chem. 2021; 86: 5778 2b Shiina I. Chem. Rev. 2007; 107: 239 2c Donald JR, Unsworth WP. Chem. Eur. J. 2017; 23: 8780 3a Boulware SL, Bronstein JC, Nordby EC, Weber PC. Antivir. Res. 2001; 51: 111 3b Cale AD, Gero TW, Walker KR, Lo YS, Welstead WJ, Jaques LW, Johnson AF, Leonard CA, Nolan JC, Johnson DN. J. Med. Chem. 1989; 32: 2178 3c Amblard M, Daffix I, Bergé G, Calmés M, Dodey P, Pruneau D, Paquet J.-L, Luccarini J.-M, Bélichard P, Martinez J. J. Med. Chem. 1999; 42: 4193 3d Schlosser KM, Krasutsky AP, Hamilton HW, Reed JE, Sexton K. Org. Lett. 2004; 6: 819 3e Binaschi M, Boldetti A, Gianni M, Maggi CA, Gensini M, Bigioni M, Parlani M, Giolitti A, Fratelli M, Valli C, Terao M, Garattini E. ACS Med. Chem. Lett. 2010; 1: 411 3f Anisetti R, Reddy MS. J. Sulfur Chem. 2012; 33: 363 3g Barbaro R, Betti L, Botta M, Corelli F, Giannaccini G, Maccari L, Manetti F, Strappaghetti G, Corsano S. J. Med. Chem. 2001; 44: 2118 4 Van den Hoven BG, Alper H. J. Am. Chem. Soc. 2001; 123: 1017 5 Ilyn AP, Loseva MV, Vvedensky VY, Putsykina EB, Tkachenko SE, Kravchenko DV, Khvat AV, Krasavin M, Ivachtchenko AV. J. Org. Chem. 2006; 71: 2811 6a Nikbakht A, Mohammadi F, Mousavi MS, Amiri K, Balalaie S, Rominger F, Bijanzadeh HR. Synthesis 2021; 53: 4654 6b Kazmaier U, Ackermann S. Org. Biomol. Chem. 2005; 3: 3184 6c Xu ZG, Ding Y, Meng JP, Tang DY, Li Y, Lei J, Xu C, Chen ZZ. Synlett 2018; 29: 2199 6d Balalaie S, Mirzaie S, Nikbakht A, Hamdan F, Rominger F, Navari R, Bijanzadeh HR. Org. Lett. 2017; 19: 6124 6e Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083 6f van der Heiden G, Jong JA. W, Ruijter E, Orru RV. A. Org. Lett. 2016; 18: 984 6g Sharma UK, Sharma N, Vachhani DD, Van der Eycken EV. Chem. Soc. Rev. 2015; 44: 1836 6h Tye H, Whittaker M. Org. Biomol. Chem. 2004; 2: 813 6i Dömling A, Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168 6j Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083 6k Wang W, Ollio S, Herdtweck E, Dömling A. J. Org. Chem. 2011; 76: 637 7a Kumar A, Li Z, Sharma SK, Parmar VS, Van der Eycken EV. Org. Lett. 2013; 15: 1874 7b Manavi B, Tejeneki HZ, Rominger F, Armaghan M, Frank W, Bijanzadeh HR, Balalaie S. Adv. Synth. Catal. 2021; 363: 4190 7c Kumar H, Prajapati G, Dubey A, Ampapathi RS, Mandal PK. Org. Lett. 2020; 22: 9258 7d Lu K, Ma Y, Gao M, Liu Y, Li M, Xu C, Zhao X, Yu P. Org. Lett. 2016; 18: 5038 7e Golmohammadi F, Balalaie S, Fathi Vavsari V, Anwar MU, Al-Harrasi A. J. Org. Chem. 2020; 85: 13141 7f Modha SG, Kumar A, Vachhani DD, Jacobs J, Sharma SK, Parmar VS, Van Meervelt L, Van der Eycken EV. Angew. Chem. Int. Ed. 2012; 51: 9572 7g Vachhani DD, Galli M, Jacobs J, Van Meervelt L, Van der Eycken EV. Chem. Commun. 2013; 49: 7171 7h Song L, Tian G, Van Meervelt L, Van der Eycken EV. Org. Lett. 2020; 22: 6537 8 Chen VY, Kwon O. Angew. Chem. Int. Ed. 2021; 60: 8874 9 CCDC 2164531 (5a) and 2164532 (6a) 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 Supplementary Material Supplementary Material Supporting Information (PDF)
