Facile synthesis of 3-(pyrazol-1-yl) succinimides from Ag₂CO₃ -catalyzed aza-Michael addition of pyrazoles to maleimides

References

• (a) Zhao, Z. F.; Yue, J. X.; Ji, X. T.; Nian, M.; Kang, K. W.; Qiao, H. F.; Zheng, X. H. Research Progress in Biological Activities of Succinimide Derivatives. Bioorg. Chem. 2021, 108, 104557. DOI: 10.1016/j.bioorg.2020.104557.
   PubMed Web of Science ®Google Scholar
• (a) Crosignani, S.; Bingham, P.; Bottemanne, P.; Cannelle, H.; Cauwenberghs, S.; Cordonnier, M.; Dalvie, D.; Deroose, F.; Feng, J. L.; Gomes, B.; et al. Discovery of a Novel and Selective Indoleamine 2,3-Dioxygenase (IDO-1) Inhibitor 3-(5-Fluoro-1 H -Indol-3-yl)Pyrrolidine-2,5-Dione (EOS200271/PF-06840003) and Its Characterization as a Potential Clinical Candidate. J. Med. Chem. 2017, 60, 9617–9629.
   PubMed Web of Science ®Google Scholar
  (b) Kudo, M.; Morimoto, M.; Moriguchi, M.; Izumi, N.; Takayama, T.; Yoshiji, H.; Hino, K.; Oikawa, T.; Chiba, T.; Motomura, K.; et al. A Randomized, Double‐Blind, Placebo‐Controlled, Phase 3 Study of Tivantinib in Japanese Patients with MET‐High Hepatocellular Carcinoma. Cancer Sci. 2020, 111, 3759–3769.
   PubMed Web of Science ®Google Scholar
  (c) Matviiuk, T.; Mori, G.; Lherbet, C.; Rodriguez, F.; Pasca, M. R.; Gorichko, M.; Guidetti, B.; Voitenko, Z.; Baltas, M. Synthesis of 3-Heteryl Substituted Pyrrolidine-2,5-Diones via Catalytic Michael Reaction and Evaluation of Their Inhibitory Activity against InhA and Mycobacterium Tuberculosis. Eur. J. Med. Chem. 2014, 71, 46–52.
   PubMed Web of Science ®Google Scholar
  (d) Mashiko, T.; Hara, K.; Tanaka, D.; Fujiwara, Y.; Kumagai, N.; Shibasaki, M. En Route to an Efficient Catalytic Asymmetric Synthesis of as-3201. J. Am. Chem. Soc. 2007, 129, 11342–11343.
   PubMed Web of Science ®Google Scholar
  (e) Isaka, M.; Rugseree, N.; Maithip, P.; Kongsaeree, P.; Prabpai, S.; Thebtaranonth, Y. Hirsutellones a–E, Antimycobacterial Alkaloids from the Insect Pathogenic Fungus Hirsutella Nivea BCC 2594. Tetrahedron 2005, 61, 5577–5583.
   Web of Science ®Google Scholar
  (f) Zhang, Y. J.; Wang, Z. L.; Sprous, D.; Nabioullin, R. In Silico Design and Synthesis of Piperazine-1-Pyrrolidine-2,5-Dione Scaffold-Based Novel Malic Enzyme Inhibitors. Bioorg. Med. Chem. Lett. 2006, 16, 525–528. DOI: 10.1021/acs.jmedchem.7b00974.
   PubMedGoogle Scholar
• (a) Bettadapur, K. R.; Lanke, V.; Prabhu, K. Ru (II)-Catalyzed C–H Activation: Ketone-Directed Novel 1,4-Addition of Ortho C–H Bond to Maleimides. Org. Lett. 2015, 17, 4658–4661.
   PubMedGoogle Scholar
  (b) Cuadros, S.; Horwitz, M. A.; Schweitzer-Chaput, B.; Melchiorre, P. A Visible-Light Mediated Three-Component Radical Process Using Dithiocarbamate Anion Catalysis. Chem. Sci. 2019, 10, 5484–5488. DOI: 10.1039/C9SC00833K.
   PubMed Web of Science ®Google Scholar
• (a) Lanke, V.; Bettadapur, K. R.; Prabhu, K. R.; 17. Site-Selective Addition of Maleimide to Indole at the C-2 Position: Ru(II)-Catalyzed C-H Activation. Org. Lett. 2015, 17, 4662–4665.
   PubMed Web of Science ®Google Scholar
  (b) Muniraj, N.; Prabhu, K. R. Co(III)-Catalyzed C–H Activation: A Site-Selective Conjugate Addition of Maleimide to Indole at the C-2 Position. ACS Omega 2017, 2, 4470–4479.
   PubMed Web of Science ®Google Scholar
  (c) Liu, S. L.; Li, Y.; Guo, J. R.; Yang, G. C.; Li, X. H.; Gong, J. F.; Song, M. P. An Approach to 3-(Indol-2-yl)Succinimide Derivatives by Manganese-Catalyzed C–H Activation. Org. Lett. 2017, 19, 4042–4045.
   PubMed Web of Science ®Google Scholar
  (d) Wróbel, M. Z.; Chodkowski, A.; Herold, F.; Gomółka, A.; Kleps, J.; Mazurek, A. P.; Pluciński, F.; Mazurek, A.; Nowak, G.; Siwek, A.; et al. Synthesis and Biological Evaluation of Novel Pyrrolidine-2,5-Dione Derivatives as Potential Antidepressant Agents. Part 1. Eur. J. Med. Chem. 2013, 63, 484–500.
   PubMed Web of Science ®Google Scholar
  (e) Wrobel, M. Z.; Chodkowski, A.; Herold, F.; Marciniak, M.; Dawidowski, M.; Siwek, A.; Starowicz, G.; Stachowicz, K.; Szewczyk, B.; Nowak, G.; et al. Synthesis and Biological Evaluation of New Multi-Target 3-(1H-Indol-3-yl)Pyrrolidine-2,5-Dione Derivatives with Potential Antidepressant Effect. Eur. J. Med. Chem 2019, 183, 111736.
   PubMed Web of Science ®Google Scholar
  (f) (Xu, M.; Wang, Y.; Yang, F.; Wu, C.; Wang, Z.; Ye, B.; Jiang, X.; Zhao, Q.; Li, J.; Liu, Y.; et al. Privileged Heterocycles for DNA-Encoded Library Design and Hit-to-Lead Optimization. Eur. J. Med. Chem. 2023, 248, 115079–115085. DOI: 10.1021/acs.orglett.5b01809.
   PubMed Web of Science ®Google Scholar
• Li, B.; Mao, Q.; Zhou, J.; Liu, F.; Ye, N. HFIP-Promoted Michael Reactions: direct Para-Selective C-H Activation of Anilines with Maleimides. Org. Biomol. Chem. 2019, 17, 2242–2246. DOI: 10.1039/c8ob03073a.
   PubMed Web of Science ®Google Scholar
• An, Y. L.; Deng, Y. X.; Zhang, W.; Zhao, S. Y. Regioselective Hetero-Michael Addition of Oxygen, Sulfur, and Nitrogen­ Nucleophiles to Maleimides Catalyzed by BF3·OEt2. Synthesis 2015, 47, 1581–1592. DOI: 10.1055/s-0034-1380404.
   Web of Science ®Google Scholar
• (a) Oulous, A.; Daoudi, N. E.; Harit, T.; Cherfi, M.; Bnouham, M.; Malek, F. New Pyrazole-Tetrazole Hybrid Compounds as Potent α-Amylase and Non-Enzymatic Glycation Inhibitors. Bioorg. Med. Chem. Lett. 2022, 69, 128785.
   PubMed Web of Science ®Google Scholar
  (b) Short, K. M.; Estiarte, M. A.; Pham, S. M.; Williams, D. C.; Igoudin, L.; Dash, S.; Sandoval, N.; Datta, A.; Pozzi, N.; Cera, E. D.; Kita, D. B. Discovery of Novel N-Acylpyrazoles as Potent and Selective Thrombin Inhibitors. Eur. J. Med. Chem. 2023, 246, 114855.
   PubMed Web of Science ®Google Scholar
  (c) Ragab, M. A.; Eldehna, W. M.; Nocentini, A.; Bonardi, A.; Okda, H. E.; Elgendy, B.; Ibrahim, T. S.; Abd-Alhaseeb, M. M.; Gratteri, P.; Supuran, C. T.; et al. 4-(5-Amino-Pyrazol-1-yl)Benzenesulfonamide Derivatives as Novel Multi-Target anti-Inflammatory Agents Endowed with Inhibitory Activity against COX-2, 5-LOX and Carbonic Anhydrase: Design, Synthesis, and Biological Assessments. Eur. J. Med. Chem. 2023, 250, 115180. DOI: 10.1016/j.ejmech.2023.115180.
   PubMed Web of Science ®Google Scholar
• (a) Yu, H. F.; Wang, W. J. Catalyst Free Cyclocondensation of β -Ethylthio- β -Indolyl- α, β -Unsaturated Ketones with Hydrazines: Efficient Synthesis of 3-Pyrazolyl Indoles. Synthetic. Commun. 2020, 50, 1133–1140.
   Web of Science ®Google Scholar
  (b) Zhao, Y. H.; Yu, H. F.; Liao, P. Q.; Wang, W. J. Green and Efficient Synthesis of 3-Pyrazolyl Indoles in Water. Chem. Res. Chin. Univ. 2020, 36, 847–852.
   Web of Science ®Google Scholar
  (c) Zhao, X. B.; Jiang, S. A.; Wang, N.; Yu, H. F. Green and Complementary Regioselective Synthesis of 3-(1 –Substituted Pyrazol-3(or 5)-yl)Indoles from β-Ethyltho-β-Indolyl-α,β-Unsaturated Ketones in Water. Synth. Commun. 2020, 50, 3404–3412.
   Web of Science ®Google Scholar
  (d) Yu, J.; Chen, X.; Liu, Y.; Wu, B.; Li, H.; Hu, Y.; Wang, L.; Zhang, S. Facile Construction of Troponoid Derivatives Incorporating Imidazolin-2-One Moieties. Synthesis 2020, 52, 1847–1854.
   Web of Science ®Google Scholar
  (e) Zhang, X.; Qiu, D. X.; Qiu, W. T.; Wang, H. R.; Zhao, Z. W.; Yu, H. F.; Che, G. B. Ag2CO3 Catalyzed Aza-Michael Addition of Pyrazoles to α, β-Unsaturated Carbonyl Compounds: A New Access to N-Alkylated Pyrazole Derivatives. Tetrahedron 2023, 134, 133305.
   Web of Science ®Google Scholar
  (f) (Zhang, X.; Zhang, Z. Y.; Yu, H. F.; Che, G. B. Regio- and Stereoselective Switchable Synthesis of (E)- and (Z)-N-Carbonylvinylated Pyrazoles. Molecules 2023, 28, 4347. DOI: 10.3390/molecules28114347.
   PubMed Web of Science ®Google Scholar
• (a) Xu, Z.; Zhao, S. J.; Lv, Z. S.; Gao, F.; Wang, Y. L.; Zhang, F.; Bai, L. Y.; Deng, J. L. Fluoroquinolone-Isatin Hybrids and Their Biological Activities. Eur. J. Med. Chem. 2019, 162, 396–406.
   PubMed Web of Science ®Google Scholar
  (b) Hassan, A. S.; Moustafa, G. O.; Awad, H. M.; Nossier, E. S.; Mady, M. F. Design, Synthesis, Anticancer Evaluation, Enzymatic Assays, and a Molecular Modeling Study of Novel Pyrazole–Indole Hybrids. ACS Omega 2021, 6, 12361–12374.
   PubMed Web of Science ®Google Scholar
  (c) Ke, S.; Shi, L.; Yang, Z. Discovery of Novel Isatin–Dehydroepiandrosterone Conjugates as Potential Anticancer Agents. Bioorg. Med. Chem. Lett. 2015, 25, 4628–4631. DOI: 10.1016/j.ejmech.2018.11.032.
   PubMed Web of Science ®Google Scholar
• Stepakov, A.; V.; Popova, E. A.; Stepakova, L. V.; Boitsov, V. M.; Starova, G. L.; Grinenko, E. V. (4 + 2) Dimerization of Imides of Arylmaleic Acids in the Presence of the 3,5-Dimethyl-1H-Pyrazole and 2,6-Lutidine. Tetrahedron 2010, 66, 5262–5269. DOI: 10.1016/j.tet.2010.04.022.
   Web of Science ®Google Scholar
• CCDC 2263559 (4a) and CCDC 2263568 (4j) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam. ac.uk/data request/cif
   Google Scholar
• (a) Bai, X. F.; Xu, Z.; Xia, C. G.; Zheng, Z. J.; Xu, L. W.; 6016-6020, 5. Aromatic-Amide-Derived Nonbiaryl Atropisomer as Highly Efficient Ligand for Asymmetric Silver-Catalyzed [3 + 2] Cycloaddition. ACS Catal. 2015, 5, 6016–6020.
   Web of Science ®Google Scholar
  (b) Li, J. Y.; Kim, H. Y.; Oh, K. Enantiodivergent Brucine Diol‐Catalyzed 1,3‐Dipolar Cycloaddition of Azomethine Ylides with α,β‐Unsaturated Ketones. Adv. Synth. Catal. 2016, 358, 984–993.
   Google Scholar
  (c) Gao, Y. L.; Hu, Z. Y.; Dong, J. H.; Liu, J.; Xu, X. X. Chemoselective Double Annulation of Two Different Isocyanides: Rapid Access to Trifluoromethylated Indole-Fused Heterocycles. Org. Lett. 2017, 19, 5292–5295. DOI: 10.1021/acs.orglett.7b02582.
   PubMed Web of Science ®Google Scholar