Synthesis of novel 1,4 naphthoquinone-based molecules by an Ugi-type four-component reaction

References

• Leyva, E. ; López, L. ; Cruz, R. ; Espinosa-González, C. G. Synthesis and Studies of the Antifungal Activity of 2-Anilino-/2,3-Dianilino-/2-Phenoxy- and 2,3-Diphenoxy-1,4-Naphthoquinones. Res. Chem. Intermediat. 2016, 43, 1813-1827. doi:10.1007/s11164-016-2732-3
   Web of Science ®Google Scholar
• Jin, Y. R. ; Ryu, C. K. ; Moon, C. K. ; Cho, M. R. ; Yun, Y. P . Inhibitory Effects of J78, a Newly Synthesized 1,4-naphthoquinone Derivative, on Experimental Thrombosis and Platelet Aggregation. Pharmacology. 2004, 70 , 195-200. doi:10.1159/000075548.
   PubMed Web of Science ®Google Scholar
• Sasaki, K. ; Abe, H. ; Yoshizaki, F . In Vitro Antifungal Activity of Naphthoquinone Derivatives. Biol. Pharm. Bull. 2002, 25 , 669-670. doi:10.1248/bpb.25.669.
   PubMed Web of Science ®Google Scholar
• (a) Domling, A. ; Ugi, I . Multicomponent Reactions with Isocyanides. Angew. Chem., Int. Ed 2000, 39 , 3168-3210. (b) Zhu, J . Recent Developments in the Isonitrile-based Multicomponent Synthesis of Heterocycles. Eur. J. Org. Chem. 2003, 2003 , 1133-1144. (c) Domling, A. Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry. Chem. Rev 2006, 106 , 17-89. (d) Akritopoulou-Zanze, I . Isocyanide-based Multicomponent Reactions in Drug Discovery. Curr. Opin.Chem. Biol. 2008, 12 , 324-331. doi:10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U
   PubMed Web of Science ®Google Scholar
• Ugi, I. ; Werner, B. ; Domling, A . The Chemistry of Isocyanides, their Multicomponent Reactions and Their Libraries. Molecules 2003, 8 , 53-66. doi:10.3390/80100053.
   Web of Science ®Google Scholar
• Ugi, I. ; Steinbrückner, C . α‐Addition Von Immonium‐ionen Und Carbonsäure‐anionen an Isonitrile. Chem. Ber. 1961, 94 , 2802. doi:10.1002/cber.19610941032.
   Google Scholar
• Heck, S. ; Dömling, A. A Versatile Multi-component One-pot Thiazole Synthesis. Synlett. 2000, 3, 424-426. doi:10.1055/s-2000-6517
   Google Scholar
• Ugi, I. ; Rosendahl, F. K. ; Bodesheim, F . Kondensation Von Primären Aminen Und Ketonen Mit Isonitrilen Und Rhodanwasserstoffsäure. Justus Liebigs Ann. Chem. 1963, 666 , 54-61. doi:10.1002/jlac.19636660107.
   Google Scholar
• (a) Bossio, R. ; Marcaccini, S. ; Paoli, P. ; Pepino, R. ; Polo, C . Studies on Isocyanides and Related Compounds. Synthesis of Benzofuran Derivatives. Synthesis. 1991, 1991 , 999-1000. (b) El Kaim, L. ; Grimaud, L . Beyond the Ugi Reaction: Less Conventional Interactions between Isocyanides and Iminium Species. Tetrahedron. 2009, 65 , 2153-2171. doi:10.1016/j.tet.2008.12.002.
   Web of Science ®Google Scholar
• Cheng, G. ; He, X. ; Tian, L. ; Chen, J. ; Li, C. ; Jia, X. ; Li, J . Ugi/Himbert Arene/Allene Diels − Alder Cycloaddition to Synthesize Strained Polycyclic Skeleton. J. Org. Chem. 2015, 80 , 11100-11107. doi:10.1021/acs.joc.5b01724
   PubMed Web of Science ®Google Scholar
• Chandgude, A. L. ; Dömling, A . N-Hydroxyimide Ugi Reaction toward α-Hydrazino Amides. Org. Lett. 2017, 19, 1228-1231. doi:10.1021/acs.orglett.7b00205
   PubMed Web of Science ®Google Scholar
• (a) Neo, A. G. ; Castellano, T. G. ; Marcos, C. F . Enol-Ugi Reaction of Hydroxycoumarins: straightforward Synthesis of Amino Acid Derived Coumarin Enamines. Synthesis. 2015, 47 , 2431-2438. (b) Castellano, T. G. ; Neo, A. G. ; Marcaccini, S. ; Marcos, C. F . Enols as Feasible Acid Components in the Ugi Condensation. Org. Lett. 2012, 14 , 6218-6221. (c). Neo, A. G. ; Marcos, C. F . Selective Synthesis of 3-substituted Pyrrolidinones by enol-Passerini and Anomalous enol-Passerini Condensations. Org. Lett. 2018, 20 , 3875-3878. doi:10.1055/s-0034-1380436
   Web of Science ®Google Scholar
• Tron, G. C . Off the Beaten Track: The Use of Secondary Amines in the Ugi Reaction. Eur. J. Org. Chem. 2013, 2013 , 1849-1859. doi:10.1002/ejoc.201201660
   Web of Science ®Google Scholar
• Giovenzana, G. B. ; Tron, G. C. ; Di Paola, S. ; Menegotto, I. ; Pirali, T . A Mimicry of Primary Amines by Bis-secondary Diamines as Components in the Ugi Four Component Reaction. Angew. Chem. Int. Ed. 2006, 45 , 1099-1102. doi:10.1002/anie.200503095.
   PubMed Web of Science ®Google Scholar
• Echemendía, R. ; de la Torre, A. F. ; Monteiro, J. L. ; Pila, M. ; Corrêa, A. G. ; Westermann, B. ; Rivera, D. G. ; Paixão, M. W . Highly Stereoselective Synthesis of Natural-product-like Hybrids by an Organocatalytic/multicomponent Reaction Sequence. Angew. Chem. Int. Ed. 2015, 54 , 7621-7625. doi:10.1002/anie.201412074.
   PubMed Web of Science ®Google Scholar