Chemoselective Aza-Michael addition of indoles with 2-arylidenemalononitriles

References

• Barman, S.; Das, G.; Mondal, P.; Pradhan, K.; Jana, B.; Bhunia, D.; Saha, A.; Kar, C.; Ghosh, S.Tripodal Molecular Propellers Perturb Microtubule Dynamics: Indole Acts as a Blade and Plays a Crucial Role in Anticancer Activity. Chem. Commun.2019, 55, 2356-2359. DOI: 10.1039/C9CC00074G.
   PubMed Web of Science ®Google Scholar
• Aksenov, A. V.; Smirnov, A. N.; Magedov, I. V.; Reisenauer, M. R.; Aksenov, N. A.; Aksenova, I. V.; Pendleton, A. L.; Nguyen, G.; Johnston, R. K.; Rubin, M.; et al. Activity of 2-Aryl-2-(3-Indolyl)Acetohydroxamates against Drug-Resistant Cancer Cells. J. Med. Chem.2015, 58, 2206-2220. DOI: 10.1021/jm501518y.
   PubMed Web of Science ®Google Scholar
• Zhang, H. C.; Derian, C. K.; McComsey, D. F.; White, K. B.; Ye, H.; Hecker, L. R.; Li, J.; Addo, M. F.; Croll, D.; Eckardt, A. J.; et al. Novel Indolylindazolylmaleimides as Inhibitors of Protein Kinase C-β: Synthesis, Biological Activity, and Cardiovascular Safety. J. Med. Chem.2005, 48, 1725-1728. DOI: 10.1021/jm049478u.
   PubMed Web of Science ®Google Scholar
• Breslin, H. J.; Miskowski, T. A.; Kukla, M. J.; De Winter, H. L.; Somers, M. V. F.; Roevens, P. W. M.; Kavash, R. W.Tripeptidyl-Peptidase II (TPP II) Inhibitory Activity of (S)-2,3-Dihydro-2-(1H-Imidazol-2-yl)-1H-Indoles, a Systematic SAR Evaluation. Part 2. Bioorg. Med. Chem. Lett.2003, 13, 4467-4471. DOI: 10.1016/j.bmcl.2003.09.014.
   PubMed Web of Science ®Google Scholar
• Hoemann, M. Z.; Kumaravel, G.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R.Potent in Vitro Methicillin-Resistant Staphylococcus aureus Activity of 2-(1H-Indol-3-yl)Quinoline Derivatives. Bioorg. Med. Chem. Lett.2000, 10, 2675-2678. DOI: 10.1016/S0960-894X(00)00542-4.
   PubMed Web of Science ®Google Scholar
• Zhao, K.; Du, R.; Wang, B.; Liu, J.; Xia, C.; Yang, L.RhCl3·3H2O-Catalyzed Regioselective C(sp2)−H Alkoxycarbonylation: Efficient Synthesis of Indole- and Pyrrole-2-Carboxylic Acid Esters. ACS Catal.2019, 9, 5545-5551. DOI: 10.1021/acscatal.9b01193.
   Web of Science ®Google Scholar
• Lai, R.; Wu, X.; Lv, S.; Zhang, C.; He, M.; Chen, Y.; Wang, Q.; Hai, L.; Wu, Y.Synthesis of Indoles and Quinazolines via Additive-Controlled Selective C − H Activation/Annulation of Narylamidines and Sulfoxonium Ylides. Chem. Commun.2019, 55, 4039-4042. DOI: 10.1039/C9CC01146C.
   PubMed Web of Science ®Google Scholar
• Shaabani, S.; Xu, R.; Ahmadianmoghaddam, M.; Gao, L.; Stahorsky, M.; Olechno, J.; Ellson, R.; Kossenjans, M.; Helan, V.; Dömling, A.Automated and Accelerated Synthesis of Indole Derivatives on a Nano-Scale. Green Chem.2019, 21, 225-232. DOI: 10.1039/C8GC03039A.
   PubMed Web of Science ®Google Scholar
• Nagaraju, K.; Ma, D.Oxidative Coupling Strategies for the Synthesis of Indole Alkaloids. Chem. Soc. Rev.2018, 47, 8018-8029. DOI: 10.1039/C8CS00305J.
   PubMed Web of Science ®Google Scholar
• Nikbakht, A.; Balalaie, S.; Baghestani, F.; Rominger, F.Efficient Synthesis of Indole Derivatives Containing the Tetrazole Moeity Utilizing an Ugi-Azide Post-Transformation Strategy. Synlett2018, 29, 1892-1896. DOI: 10.1055/s-0037-1610502.
   Web of Science ®Google Scholar
• Lin, W.; Zheng, Y. X.; Xun, Z.; Huang, Z. B.; Shi, D. Q.Microwave-Assisted Regioselective Synthesis of 3-Functionalized Indole Derivatives via Three-Component Domino Reaction. ACS Comb. Sci.2017, 19, 708-713. DOI: 10.1021/acscombsci.7b00126.
   PubMed Web of Science ®Google Scholar
• Zheng, M.; Chen, K.; Zhu, S.One-Pot Synthesis of Indole Derivatives from the Reaction of Nitroalkynes and Alkynes via a Mercury-Carbene Intermediate. Synthesis2017, 49, 4173-4182. DOI: 10.1055/s-0036-1588416.
   Web of Science ®Google Scholar
• Anderson, L. L.; Kroc, M. A.; Reidl, T. W.; Son, J.Cascade Reactions of Nitrones and Allenes for the Synthesis of Indole Derivatives. J. Org. Chem.2016, 81, 9521-9529. DOI: 10.1021/acs.joc.6b01758.
   PubMed Web of Science ®Google Scholar
• Clagg, K.; Hou, H.; Weinstein, A. B.; Russell, D.; Stahl, S. S.; Koenig, S. G.Synthesis of Indole-2-Carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C − H Bonds. Org. Lett.2016, 18, 3586-3589. DOI: 10.1021/acs.orglett.6b01592.
   PubMedGoogle Scholar
• Feng, Y.; Zhang, H.; Cheng, G.; Cui, X.Synthesis of Indole Derivatives via Domino Reactions. Chin. J. Org. Chem.2014, 34, 1499-1508. DOI: 10.6023/cjoc201403015.
   Google Scholar
• Li, Y. L.; Li, J.; Ma, A. L.; Huang, Y. N.; Deng, J.Metal-Free Synthesis of Indole via NIS-Mediated Cascade C − N Bond Formation/Aromatization. J. Org. Chem.2015, 80, 3841-3851. DOI: 10.1021/acs.joc.5b00090.
   PubMed Web of Science ®Google Scholar
• Su, W. Q.; Yang, C.; Xu, D. Z.Ionic Liquid [dabco-C8][FeCl4] as an Efficient and Recyclable Catalyst for Direct C3 Alkylation of Indoles with Electron-Deficient Olefins. Catal. Commun.2017, 100, 38-42. DOI: 10.1016/j.catcom.2017.06.018.
   Web of Science ®Google Scholar
• Desyatkin, V. G.; Beletskaya, I. P.Asymmetric Friedel-Crafts/Michael Reaction of Indoles and Pyrroles with Coumarin-3-Carbonylates. Synthesis2017, 49, 4327-4334. DOI: 10.1055/s-0036-1589024.
   Web of Science ®Google Scholar
• Romanini, S.; Galletti, E.; Caruana, L.; Mazzanti, A.; Himo, F.; Santoro, S.; Fochi, M.; Bernardi, L.Catalytic Asymmetric Reactions of 4-Substituted Indoles with Nitroethene: A Direct Entry to Ergot Alkaloid Structures. Chem. Eur. J.2015, 21, 17578-17582. DOI: 10.1002/chem.201502655.
   PubMed Web of Science ®Google Scholar
• Parsekar, S. B.; Naik, S.; Naik, M. M.; Tilve, S. G.Graphite as an Effective Catalyst for Michael Addition of Indoles to Nitroolefins in Aqueous Alcoholic Solution. Monatsh. Chem.2015, 146, 691-696. DOI: 10.1007/s00706-014-1347-x.
   Web of Science ®Google Scholar
• Liu, R.; Zhang, J.Organocatalytic Michael Addition of Indoles to Isatylidene-3-Acetaldehydes: Application to the Formal Total Synthesis of (-)-Chimonanthine. Org. Lett.2013, 15, 2266-2269. DOI: 10.1021/ol400845c.
   PubMed Web of Science ®Google Scholar
• Singh, S. K.; Singh, K. N.An Efficient and Mild Superoxide-Induced Michael Addition of Indoles to α,β-Unsaturated Ketones. J. Indian Chem. Soc2012, 89, 401-404.
   Web of Science ®Google Scholar
• Gupta, P.; Paul, S.Sulfonated Carbon/Silica Composite Functionalized Lewis Acids for One-Pot Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles, 3,4-Dihydropyrimidin-2(1H)-Ones and for Michael Addition of Indole to α,β-Unsaturated Ketones. J. Mol. Catal. A: Chem.2012, 352, 75-80. DOI: 10.1016/j.molcata.2011.10.016.
   Google Scholar
• Liu, X. L.; Xue, D.; Zhang, Z. T.An Efficient and Clean Michael Addition of Indoles to Electron-Deficient Olefins under Solvent- and Catalyst-Free Condition. J. Heterocyclic Chem.2011, 48, 489-494. DOI: 10.1002/jhet.569.
   Web of Science ®Google Scholar
• Hanessian, S.; Stoffman, E.; Mi, X.; Renton, P.Applications of Organocatalytic Asymmetric Synthesis to Drug Prototypes-Dual Action and Selective Inhibitors of n-Nitric Oxide Synthase with Activity against the 5-HT1D/1B Subreceptors. Org. Lett.2011, 13, 840-843. DOI: 10.1021/ol102795g.
   PubMed Web of Science ®Google Scholar
• Shen, W.; Wang, L.; Tang, J.; Qian, Z.; Tong, X.Ionic Liquid-Coordinated Ytterbium(III) Sulfonate Catalyzed Michael Addition of Indoles to Electron-Deficient Nitroolefins. Chin. J. Chem.2010, 28, 443-448. DOI: 10.1002/cjoc.201090094.
   Web of Science ®Google Scholar
• Joucla, L.; Djakovitch, L.Transition Metal-Catalysed, Direct and Site-Selective N1-, C2- or C3-Arylation of the Indole Nucleus: 20 Years of Improvements. Adv. Synth. Catal.2009, 351, 673-714. DOI: 10.1002/adsc.200900059.
   Web of Science ®Google Scholar
• Karchava, A. V.; Melkonyan, F. S.; Yurovskaya, M. A.New Strategies for the Synthesis of N-Alkylated Indoles (Review). Chem. Heterocycl. Comp. 2012, 48, 391-407. DOI: 10.1007/s10593-012-1006-2.
   Web of Science ®Google Scholar
• Larionov, V. A.; Savel'yeva, T. F.; Medvedev, M. G.; Stoletova, N. V.; Smol'yakov, A. F.; Gugkaeva, Z. T.; Cruchter, T.; Maleev, V. I.The Selective N-Functionalization of Indoles via aza-Michael Addition in the Ligand Sphere of a Chiral Nickel(II) Complex: Asymmetric Synthesis of (S)-1H-Indole-Alanine Derivatives. Eur. J. Org. Chem.2019, 2019, 3699-3703. DOI: 10.1002/ejoc.201900650.
   Web of Science ®Google Scholar
• Mukherjee, S.; Shee, S.; Poisson, T.; Besset, T.; Biju, A. T.Enantioselective N-Heterocyclic Carbene-Catalyzed Cascade Reaction for the Synthesis of Pyrroloquinolines via N − H Functionalization of Indoles. Org. Lett.2018, 20, 6998-7002. DOI: 10.1021/acs.orglett.8b02820.
   PubMed Web of Science ®Google Scholar
• Yang, J.; Li, T.; Zhou, H.; Li, N.; Xie, D.; Li, Z.Potassium Hydroxide Catalyzed Intermolecular aza-Michael Addition of 3-Cyanoindole to Aromatic Enones. Synlett2017, 28, 1227-1231. DOI: 10.1055/s-0036-1588152.
   Web of Science ®Google Scholar
• He, Y. H.; Cao, J. F.; Li, R.; Xiang, Y.; Yang, D. C.; Guan, Z.L-Proline-Catalyzed Multicomponent Synthesis of 3-Indole Derivatives. Tetrahedron2015, 71, 9299-9306. DOI: 10.1016/j.tet.2015.10.027.
   Web of Science ®Google Scholar
• Pasala, V. K.PMA-SiO2: Heteropolyacid Catalysis for Michael Addition-Convenient Route to Substituted-3-Indoles. Pharma. Chem.2017, 9, 112-117.
   Google Scholar
• Jari, T.; Amrollahi, M. A.; Kheilkordi, Z.ZrOCl2·SiO2-Catalyzed Synthesis of Bis(Indoles) via Conjugate Addition of Indole with Electron-Deficient Alkenes in Water. Heterocycl. Commun.2015, 21, 89-92. DOI: 10.1515/hc-2015-0014.
   Web of Science ®Google Scholar
• Li, J. T.; Lin, Z. P.An Efficient and Practical Synthesis of 2-((1H-Indol-3-yl)(Aryl)Methyl]Malononitriles under Ultrasound Irradiation. Ultrason. Sonochem.2008, 15, 265-268. DOI: 10.1016/j.ultsonch.2007.08.005.
   PubMed Web of Science ®Google Scholar
• Das, S.; Rahman, M.; Kundu, D.; Majee, A.; Hajra, A.Task-Specific Ionic-Liquid-Catalyzed Efficient Synthesis of Indole Derivatives under Solvent-Free Conditions. Can. J. Chem.2010, 88, 150-154. DOI: 10.1139/V09-154.
   Web of Science ®Google Scholar
• Sobhani, S.; Jahanshahi, R.Nano n-Propylsulfonated γ-Fe2O3 (NPS-γ-Fe2O3) as a Magnetically Recyclable Heterogeneous Catalyst for the Efficient Synthesis of 2-Indolyl-1-Nitroalkanes and Bis(Indolyl)Methanes. New J. Chem.2013, 37, 1009-1015. DOI: 10.1039/c3nj40899j.
   Web of Science ®Google Scholar
• Ferreira, J. M. G. O.; Filho, J. B. M. R.; Batista, P. K.; Teotonio, E. E. S.; Vale, J. A.Rapid and Efficient Uncatalyzed Knoevenagel Condensations from Binary Mixture of Ethanol and Water. J. Braz. Chem. Soc.2018, 29, 1382-1387. DOI: 10.21577/0103-5053.20170240.
   Web of Science ®Google Scholar