Radical-mediated dehydrative preparation of cyclic imides using (NH₄)₂S₂O₈–DMSO: application to the synthesis of vernakalant

Scholarly Works

• Ma, C.; Hu, Q.; Qin, H.; Yang, G.; Chai, Z. Synthesis of Chiral Vicinal Amino Alcohol Derivatives via Lewis Acid‐Catalyzed Asymmetric Ring Opening of Aziridines with Alcohols and Carboxylic Acids. Advanced Synthesis & Catalysis 2024. doi:10.1002/adsc.202301429
• Tretyakov, B. A.; Gadomsky, S. Y.; Terentiev, A. A. A Reaction of N-Substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids. Organics 2023, 4, 186–195. doi:10.3390/org4020015
• Sanada, K.; Washio, A.; Nishihata, K.; Yagishita, F.; Yoshida, Y.; Mino, T.; Suzuki, S.; Kasashima, Y.; Sakamoto, M. Chiral Symmetry Breaking of Racemic 3-Phenylsuccinimides via Crystallization-Induced Dynamic Deracemization. Crystal Growth & Design 2021, 21, 6051–6055. doi:10.1021/acs.cgd.1c01010
• Bhattacharjee, S.; Laru, S.; Ghosh, P.; Hajra, A. Potassium Persulfate Mediated Chemodivergent C-3 Functionalization of 2H-Indazoles with DMSO as C1 Source. The Journal of organic chemistry 2021, 86, 10866–10873. doi:10.1021/acs.joc.1c01188
• Rasheed, M. K.; Subhi, D. S. M.; Abdulrahnan, A. M. Synthesis, characterization of amic acids and cyclic imides derived from acriflavine and evaluation of their antibacterial and antioxidant activity. Materials Today: Proceedings 2021, 43, 2051–2058. doi:10.1016/j.matpr.2020.11.842
• Thobokholt, E. N.; Larghi, E. L.; Bracca, A. B. J.; Kaufman, T. S. Isolation and synthesis of cryptosanguinolentine (isocryptolepine), a naturally-occurring bioactive indoloquinoline alkaloid. RSC advances 2020, 10, 18978–19002. doi:10.1039/d0ra03096a
• Sydnes, M. O. Recent progress in the synthesis of antimalarial indoloquinoline natural products and analogues. Bioactive Natural Products; Elsevier, 2020; Vol. 64, pp 59–84. doi:10.1016/b978-0-12-817903-1.00002-4
• Lockett-Walters, B.; Trujillo, C.; Twamley, B.; Connon, S. J. The base-catalysed Tamura cycloaddition reaction: calculation, mechanism, isolation of intermediates and asymmetric catalysis. Chemical communications (Cambridge, England) 2019, 55, 11283–11286. doi:10.1039/c9cc05064g
• Sherikar, M. S.; Prabhu, K. R. Weak Coordinating Carboxylate Directed Rhodium(III)-Catalyzed C–H Activation: Switchable Decarboxylative Heck-Type and [4 + 1] Annulation Reactions with Maleimides. Organic letters 2019, 21, 4525–4530. doi:10.1021/acs.orglett.9b01412
• Manoharan, R.; Jeganmohan, M. Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition‐Metal‐Catalyzed C‐H Bond Activation. Asian Journal of Organic Chemistry 2019, 8, 1949–1969. doi:10.1002/ajoc.201900054
• Yang, Z.; Guo, Y.; Ai, S.-L.; Wang, S.; Jinzhi, Z.; Zhang, Y.; Qichao, Z.; Wang, H.-X. Rational design and facile preparation of maleimide-based functional materials for imaging and optoelectronic applications. Materials Chemistry Frontiers 2019, 3, 571–578. doi:10.1039/c8qm00559a
• Aitken, R. A. Synthesis of Cyclic Imides. Imides; Elsevier, 2019; pp 1–28. doi:10.1016/b978-0-12-815675-9.00001-1
• Hassanzadeh, F.; Jafari, E. Cyclic imide derivatives: As promising scaffold for the synthesis of antimicrobial agents. Journal of research in medical sciences : the official journal of Isfahan University of Medical Sciences 2018, 23, 53. doi:10.4103/jrms.jrms_539_17
• Matías, D. M.; Johnson, J. S. Synthesis and Desymmetrization of meso Tricyclic Systems Derived from Benzene Oxide. The Journal of organic chemistry 2018, 83, 4859–4866. doi:10.1021/acs.joc.8b00523
• Ahire, M. M.; Mhaske, S. B. Isa‒NHC‒catalyzed intermolecular Stetter reaction of aromatic aldehydes with maleimides: An efficient access to 3‒aroylsuccinimides. Tetrahedron 2018, 74, 2079–2084. doi:10.1016/j.tet.2018.03.009
• Abel, A. S.; Averin, A. D.; Savelyev, E. N.; Orlinson, B. S.; Novakov, I. A.; Beletskaya, I. P. Phosphine-catalyzed [3 + 2] cycloaddition of ethyl buta-2,3-dienoate to adamantane-containing N-substituted maleimides. Mendeleev Communications 2017, 27, 550–552. doi:10.1016/j.mencom.2017.11.003
• Yoshida, Y.; Endo, T. Dependence of color change of vinylethylene carbonate copolymers having N-substituted maleimides on chemical structure by acid-base switching in solution and solid state. Reactive and Functional Polymers 2017, 120, 139–146. doi:10.1016/j.reactfunctpolym.2017.10.001
• Ahire, M. M.; Mhaske, S. B. Synthesis of Succinimide Derivatives by NHC-Catalyzed Stetter Reaction of Aromatic Aldehydes with N-Substituted Itaconimides. ACS omega 2017, 2, 6598–6604. doi:10.1021/acsomega.7b01213
• Mandal, A.; Sahoo, H.; Dana, S.; Baidya, M. Ruthenium(II)-Catalyzed Hydroarylation of Maleimides Using Carboxylic Acids as a Traceless Directing Group. Organic letters 2017, 19, 4138–4141. doi:10.1021/acs.orglett.7b01964
• Mahajan, P. S.; Humne, V. T.; Tanpure, S. D.; Mhaske, S. B. Radical Beckmann Rearrangement and Its Application in the Formal Total Synthesis of Antimalarial Natural Product Isocryptolepine via C-H Activation. Organic letters 2016, 18, 3450–3453. doi:10.1021/acs.orglett.6b01634

Explore citations to this article at