Multicomponent reaction access to complex quinolines via oxidation of the Povarov adducts

Scholarly Works

• Zhu, C.; Nurko, M.; Day, C. S.; Lukesh, J. C. Arylselenyl Radical-Mediated Cyclization of N-(2-Alkynyl)anilines: Access to 3-Selenylquinolines. The Journal of organic chemistry 2022, 87, 8390–8395. doi:10.1021/acs.joc.2c00282
• Rani, V. A.; Kumari, Y. B. DBU(OAc)–TBAB-Mediated One-Pot Three-component Synthesis of 1H-Imidazol-5(4H)-one Derivatives. Russian Journal of Organic Chemistry 2022, 58, 352–355. doi:10.1134/s1070428022030125
• de Fátima, Â.; Fernandes, S. A.; Ferreira de Paiva, W.; de Freitas Rego, Y. The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines. Synthesis 2022, 54, 3162–3179. doi:10.1055/a-1794-8355
• Soni, R.; Soman, S. S. Metal Free Synthesis of Coumarin Containing Hetero[n]helicene like Molecules with TICT and AIE Properties. Asian Journal of Organic Chemistry 2022, 11. doi:10.1002/ajoc.202100770
• Lavilla, R.; Ghashghaei, O.; Rodríguez, P. N. Development of Heterocyclic Multicomponent Reactions through Guided Exploration: Direct, Reasonable and Unpredictable Processes. Synlett 2022, 33, 822–835. doi:10.1055/a-1750-3185
• Vil', V. A.; Grishin, S. S.; Baberkina, E. P.; Alekseenko, A. L.; Glinushkin, A. P.; Kovalenko, A. E.; Terent'ev, A. O. Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza‐Diels‐Alder Cycloaddition. Advanced Synthesis & Catalysis 2022, 364, 1098–1108. doi:10.1002/adsc.202101355
• Oliveras, J. M.; de la Bellacasa, R. P.; Estrada-Tejedor, R.; Teixidó, J.; Borrell, J. I. 1,6-Naphthyridin-2(1H)-ones: Synthesis and Biomedical Applications. Pharmaceuticals (Basel, Switzerland) 2021, 14, 1029. doi:10.3390/ph14101029
• Keri, R. S.; Patil, M. R.; Budagumpi, S.; Sasidhar, B. S. An efficient, multicomponent synthesis of aminoalkylnaphthols via Betti reaction using ZSM-5 as a recoverable and reusable catalyst. Applied Organometallic Chemistry 2021, 35. doi:10.1002/aoc.6316
• Jayaraj, S.; Badu-Tawiah, A. K. N-Substituted Auxiliaries for Aerobic Dehydrogenation of Tetrahydro-isoquinoline: A Theory-Guided Photo-Catalytic Design. Scientific reports 2019, 9, 11280. doi:10.1038/s41598-019-47735-y
• Muthukrishnan, I.; Sridharan, V.; Menéndez, J. C. Progress in the Chemistry of Tetrahydroquinolines. Chemical reviews 2019, 119, 5057–5191. doi:10.1021/acs.chemrev.8b00567
• Shelkovnikov, V. V.; Kargapolova, I. Y.; Korotaev, S. V.; Orlova, N. A.; Rybalova, T. V.; Chuikov, I. P. Three-color luminescent transformation of the julolidine pyrylo/pyridocyanine dyes in the adsorbed state. Journal of Photochemistry and Photobiology A: Chemistry 2019, 375, 181–190. doi:10.1016/j.jphotochem.2019.02.022
• Smietana, M.; Benedetti, E.; Bressy, C.; Arseniyadis, S. Efficiency in Natural Product Total Synthesis; Wiley, 2018; pp 319–344. doi:10.1002/9781118940228.ch8
• Gómez, C. M. M.; Marsiglia, M.; Escarsena, R.; del Olmo, E.; Kouznetsov, V. V. Synthesis of 2,3-di(ω-hydroxyalkyl)quinolines from anilines and cyclic enols using sequential cycloaddition/aromatization reactions. Tetrahedron Letters 2018, 59, 22–25. doi:10.1016/j.tetlet.2017.11.034
• Vasconcelos, S. N. S.; da Silva, V. H. M.; Braga, A. A. C.; Shamim, A.; Souza, F. B.; Pimenta, D. C.; Stefani, H. A. 3‐Alkenyltyrosines Accessed by Suzuki–Miyaura Coupling: A Key Intermediate in the Synthesis and Mechanistic Study of Povarov Multicomponent Reactions. Asian Journal of Organic Chemistry 2017, 6, 913–920. doi:10.1002/ajoc.201700154
• Wan, J.-P.; Jing, Y.; Wei, L. Branched C=C and C−N Bond Cleavage on Enaminones toward the Synthesis of 3‐Acyl Quinolines. Asian Journal of Organic Chemistry 2017, 6, 666–668. doi:10.1002/ajoc.201700116
• Brown, C. E.; McNulty, J.; Bordon, C.; Yolken, R.; Jones-Brando, L. Enol ethers as carbonyl surrogates in a modification of the Povarov synthesis of 3-aryl quinolines and their anti-Toxoplasma activity. Organic & biomolecular chemistry 2016, 14, 5951–5955. doi:10.1039/c6ob01083k
• Bhupathi, R.; Madhu, B.; Devi, B. R.; Reddy, C. V. R.; Dubey, P. K. DBU acetate mediated: one‐pot multi component syntheses of dihydropyrano[3,2‐c]quinolones. Journal of Heterocyclic Chemistry 2015, 53, 1911–1916. doi:10.1002/jhet.2506
• Mordhorst, T.; Awal, S.; Jordan, S.; Petters, C.; Sartoris, L.; Dringen, R.; Bickmeyer, U. The Chemically Synthesized Ageladine A-Derivative LysoGlow84 Stains Lysosomes in Viable Mammalian Brain Cells and Specific Structures in the Marine Flatworm Macrostomum lignano. Marine drugs 2015, 13, 920–935. doi:10.3390/md13020920
• Di Pietro, O.; Pérez-Areales, F. J.; Juárez-Jiménez, J.; Espargaró, A.; Clos, M. V.; Pérez, B.; Lavilla, R.; Sabaté, R.; Luque, F. J.; Muñoz-Torrero, D. Tetrahydrobenzo[h][1,6]naphthyridine-6-chlorotacrine hybrids as a new family of anti-Alzheimer agents targeting β-amyloid, tau, and cholinesterase pathologies. European journal of medicinal chemistry 2014, 84, 107–117. doi:10.1016/j.ejmech.2014.07.021
• Ahmed, A.; Dhara, S.; Singha, R.; Nuree, Y.; Sarkar, P.; Ray, J. K. Palladium catalyzed one-pot synthesis of 2-(pyridin-4-yl) quinolines via a multicomponent unprecedented reaction of pyridine-4-carbaldehyde, 2-iodoaniline and triethylamine. RSC Adv. 2014, 4, 53137–53141. doi:10.1039/c4ra08624d

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