Facile synthesis of benzothiadiazine 1,1-dioxides, a precursor of RSV inhibitors, by tandem amidation/intramolecular aza-Wittig reaction

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• Govindan, K.; Jayaram, A.; Duraisamy, T.; Chen, N.-Q.; Lin, W.-Y. Metal-Free N-H/C-H Carbonylation by Phenyl Isocyanate: Divergent Synthesis of Six-Membered N-Heterocycles. The Journal of organic chemistry 2022, 87, 8719–8729. doi:10.1021/acs.joc.2c01026
• Kolade, S. O.; Izunobi, J. U.; Hosten, E. C.; Olasupo, I. A.; Ogunlaja, A. S.; Familoni, O. B. Synthesis, crystal structure and docking studies of tetracyclic 10-iodo-1,2-dihydroisoquinolino[2,1-b][1,2,4]benzothiadiazine 12,12-dioxide and its precursors. Acta crystallographica. Section C, Structural chemistry 2020, 76, 810–820. doi:10.1107/s2053229620009626
• Tatevosyan, S. S.; Kotovshchikov, Y. N.; Latyshev, G. V.; Erzunov, D. A.; Sokolova, D. V.; Beletskaya, I. P.; Lukashev, N. V. A Route to Triazole-Fused Sultams via Metal-Free Base-Mediated Cyclization of Sulfonamide-Tethered 5-Iodotriazoles. The Journal of organic chemistry 2020, 85, 7863–7876. doi:10.1021/acs.joc.0c00520
• Kornahrens, A. F.; Cognetta, A. B.; Brody, D. M.; Matthews, M. L.; Cravatt, B. F.; Boger, D. L. Design of Benzoxathiazin-3-one 1,1-Dioxides as a New Class of Irreversible Serine Hydrolase Inhibitors: Discovery of a Uniquely Selective PNPLA4 Inhibitor. Journal of the American Chemical Society 2017, 139, 7052–7061. doi:10.1021/jacs.7b02985
• Kundu, P.; Mondal, A.; Chowdhury, C. A Palladium-Catalyzed Method for the Synthesis of 2-(α-Styryl)-2,3-dihydroquinazolin-4-ones and 3-(α-Styryl)-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide: Access to 2-(α-Styryl)quinazolin-4(3H)-ones and 3-(α-Styryl)-1,2,4-benzothiadiazine-1,1-dioxides. The Journal of organic chemistry 2016, 81, 6596–6608. doi:10.1021/acs.joc.6b01242
• Xi, L.-Y.; Zhang, R.-Y.; Shi, L.; Chen, S.-Y.; Yu, X.-Q. Iodine-mediated synthesis of 3-acylbenzothiadiazine 1,1-dioxides. Beilstein journal of organic chemistry 2016, 12, 1072–1078. doi:10.3762/bjoc.12.101
• Wang, D.; Liu, W.; Yi, F.; Zhao, Y.; Chen, J. Palladium-catalyzed direct C–H arylation of 3-aryl-2H-benzo[1,2,4]thiadiazine 1,1-dioxides: an efficient strategy to the synthesis of benzothiadiazine-1,1-dioxide derivatives. Organic & biomolecular chemistry 2016, 14, 1921–1924. doi:10.1039/c5ob02196k
• Welsch, S. J.; Umkehrer, M.; Kalinski, C.; Ross, G.; Burdack, C.; Kolb, J.; Wild, M.; Ehrlich, A.; Wessjohann, L. A. Synthesis of substituted imidazolines by an Ugi/Staudinger/aza-Wittig sequence. Tetrahedron Letters 2015, 56, 1025–1029. doi:10.1016/j.tetlet.2015.01.043
• Sharif, M.; Opalach, J.; Langer, P.; Beller, M.; Wu, X.-F. Oxidative synthesis of quinazolinones and benzothiadiazine 1,1-dioxides from 2-aminobenzamide and 2-aminobenzenesulfonamide with benzyl alcohols and aldehydes. RSC Adv. 2014, 4, 8–17. doi:10.1039/c3ra45765f
• Kumar, S. K.; Rambabu, D.; Kumar, C. H. V.; Sreenivas, B. Y.; Prasad, K.; Rao, M. V. B.; Pal, M. Catalysis by Amberlyst-15 under ultrasound in water: a green synthesis of 1,2,4-benzothiadiazine-1,1-dioxides and their spiro derivatives. RSC Advances 2013, 3, 24863–24867. doi:10.1039/c3ra44703k

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