Metal-free one-pot synthesis of 2-substituted and 2,3-disubstituted morpholines from aziridines

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• Tyagi, A.; Chauhan, M.; Nain, S. An Update on the Green Synthesis of Benzimidazole Scaffolds as Antifungal Agents. Pharmaceutical Chemistry Journal 2024, 58, 816–827. doi:10.1007/s11094-024-03210-1
• Tu, J.-L.; Huang, B. Acyloxy, sulfate, and phosphate radicals as hydrogen atom transfer (HAT) agents for direct C(sp3)–H functionalization. RSC Sustainability 2024. doi:10.1039/d4su00520a
• Singh, B.; Kumar, M.; Goswami, G.; Verma, I.; Ghorai, M. K. Ring-Opening Cyclization (ROC) of Aziridines with Propargyl Alcohols: Synthesis of 3,4-Dihydro-2H-1,4-oxazines. The Journal of organic chemistry 2023, 88, 4504–4518. doi:10.1021/acs.joc.2c03093
• Lin, Y.-C.; Martinez-Brokaw, C. D.; Pierce, J. G. Comprehensive Heterocyclic Chemistry IV - 1,4-Oxazines and Their Benzo Derivatives. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 480–529. doi:10.1016/b978-0-12-818655-8.00036-6
• Elgemeie, G. H.; Azzam, R. A.; Zaghary, W. A.; Aly, A. A.; Metwally, N. H.; Sarhan, M. O.; Abdelhafez, E. M.; Elsayed, R. E. Synthetic approaches and biological evaluation of N-sulfonated N-azines. N-Sulfonated-N-Heterocycles; Elsevier, 2022; pp 253–301. doi:10.1016/b978-0-12-822179-2.00009-4
• Tarannum, S.; Chauhan, N.; Ghorai, M. K. Aziridines and 2H-Azirines—Monocyclic. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 1–114. doi:10.1016/b978-0-12-409547-2.14954-6
• Phillips, A. M. F.; Pombeiro, A. J. L. Synthetic Approaches to Nonaromatic Nitrogen Heterocycles; Wiley, 2020; pp 437–500. doi:10.1002/9781119708841.ch15
• Beng, T. K.; Moreno, A. Copper-catalyzed alkenylation of novel N-iodoarylated allylic ketopiperazinonates with unactivated alkenes. New Journal of Chemistry 2020, 44, 4257–4261. doi:10.1039/c9nj06178a
• Tzara, A.; Xanthopoulos, D.; Kourounakis, A. P. Morpholine As a Scaffold in Medicinal Chemistry: An Update on Synthetic Strategies. ChemMedChem 2020, 15, 392–403. doi:10.1002/cmdc.201900682
• Kumari, A.; Singh, R. K. Morpholine as ubiquitous pharmacophore in medicinal chemistry: Deep insight into the structure-activity relationship (SAR). Bioorganic chemistry 2020, 96, 103578. doi:10.1016/j.bioorg.2020.103578
• Park, W.; Kim, Y.; Park, Y. S. Neutral Alcohol Nucleophiles for the Substitution of α‐Bromo Aryl Acetates and Applications to Asymmetric Synthesis of Morpholine Derivatives. European Journal of Organic Chemistry 2019, 2019, 2671–2674. doi:10.1002/ejoc.201900207
• Kawauchi, D.; Ueda, H.; Tokuyama, H. Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis. European Journal of Organic Chemistry 2019, 2019, 2056–2060. doi:10.1002/ejoc.201900088
• Goswami, G.; Chauhan, N.; Mal, A.; Das, S.; Das, M.; Ghorai, M. K. Synthesis of 3,3-Diaryl/Heteroarylpropylamines via Nucleophilic Ring Opening of Activated Azetidines with Arenes and Heteroarenes: New Synthetic Route to (±)Tolterodine. ACS Omega 2018, 3, 17562–17572. doi:10.1021/acsomega.8b02487
• Akhtar, R.; Naqvi, S. A. R.; Zahoor, A. F.; Saleem, S. Nucleophilic ring opening reactions of aziridines. Molecular diversity 2018, 22, 447–501. doi:10.1007/s11030-018-9829-0
• Kapoor, R.; Tripathi, S.; Singh, S. N.; Keshari, T.; Yadav, L. D. S. Visible light triggered regioselective ring expansion of N-tosylaziridines: An efficient approach to 2-nitroazetidines. Tetrahedron Letters 2017, 58, 3814–3818. doi:10.1016/j.tetlet.2017.08.042
• Mal, A.; Sayyad, M.; Wani, I. A.; Ghorai, M. K. Domino Ring-Opening Cyclization of Activated Aziridines with Indoles: Synthesis of Chiral Hexahydropyrroloindoles. The Journal of organic chemistry 2016, 82, 4–11. doi:10.1021/acs.joc.6b01731
• Braunstein, H.; Langevin, S.; Khim, M.; Adamson, J.; Hovenkotter, K.; Kotlarz, L.; Mansker, B.; Beng, T. K. Modular access to vicinally functionalized allylic (thio)morpholinonates and piperidinonates by substrate-controlled annulation of 1,3-azadienes with hexacyclic anhydrides. Organic & biomolecular chemistry 2016, 14, 8864–8872. doi:10.1039/c6ob01526c
• Badenock, J. C. Three-Membered Ring Systems. Progress in Heterocyclic Chemistry 2016, 28, 57–94. doi:10.1016/b978-0-08-100755-6.00003-x
• Meyer, A. G.; Smith, J. A.; Hyland, C.; Williams, C. C.; Bissember, A. C.; Nicholls, T. P. Seven-Membered Rings. Progress in Heterocyclic Chemistry; Elsevier, 2016; pp 579–622. doi:10.1016/b978-0-08-100755-6.00016-8
• Matlock, J. V.; Svejstrup, T. D.; Songara, P.; Overington, S.; McGarrigle, E. M.; Aggarwal, V. K. Synthesis of 6- and 7-Membered N-Heterocycles Using α-Phenylvinylsulfonium Salts. Organic letters 2015, 17, 5044–5047. doi:10.1021/acs.orglett.5b02516

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