A Novel and Efficient Isocyanide-Catalyzed Addition Reaction of Enaminones to Isatin Derivatives for Oxindoles Synthesis

References

• S.R. Shaikh and G.M. Nazeruddin, “Multi Component Reactions and Non-Steroidal anti-Inflammatory Drugs,” Cheminform 46, no. 25 (2015): 34.
   Google Scholar
• A. Dömling, W. Wang, and K. Wang, “Chemistry and Biology of Multicomponent Reactions,” Chemical Reviews 112, no. 6 (2012): 3083–35.
   PubMed Web of Science ®Google Scholar
• M. Stucchi, G. Lesma, F. Meneghetti, G. Rainoldi, A. Sacchetti, and A. Silvani, “Organocatalytic Asymmetric Biginelli-like Reaction Involving Isatin,” The Journal of Organic Chemistry 81, no. 5 (2016): 1877–84.
   PubMed Web of Science ®Google Scholar
• A.Y. Elah-Abadi, N. Simin, R. Morekian, and H. Heydari-Dahoei, “Microwave-Promoted Facile and Rapid Access to Novel Spirooxindole-Furo[2,3 c]Pyrazole Derivatives Using Pyridinium Ylide-Assisted Domino Reaction,” Polycyclic Aromatic Compounds (2019): 1–10.
   Web of Science ®Google Scholar
• Y.-M. Wang, H.-H. Zhang, C. Li, T. Fan, and F. Shi, “Catalytic Asymmetric Chemoselective 1,3-Dipolar Cycloadditions of an Azomethine Ylide with Isatin-Derived Imines: Diastereo- and Enantioselective Construction of a Spiro[Imidazolidine-2,3'-Oxindole] Framework,” Chemical Communications (Cambridge, England) 52, no. 9 (2016): 1804–7.
   PubMed Web of Science ®Google Scholar
• M. Keshavarz, M. Tabatabaee, M. Shahabi, and E. Yazdankish, “A Sulfonated Phenanthrolinum Salt of Phosphotungstate as Novel Catalyst for the Efficient Synthesis of 3,30-Diaryloxindoles,” Polycyclic Aromatic Compounds (2019): 1–13.
   Web of Science ®Google Scholar
• Y. Zhang, B.-W. Wei, H. Lin, L. Zhang, J.-X. Liu, H.-Q. Luo, and X.-L. Fan, “On Water” Directly Catalytic Vinylogous Henry (Nitroaldol) Reactions of Isatins for the Efficient Synthesis of Isoxazole Substituted 3hydroxyindolin-2-Ones,” Green Chemistry 17, no. 6 (2015): 3266–70.
   Web of Science ®Google Scholar
• Q.N. Zhu, Y.C. Zhang, M.M. Xu, X.X. Sun, X. Yang, and F. Shi, “Enantioselective Construction of Tetrahydroquinolin-5-one-Based Spirooxindole Scaffold via an Organocatalytic Asymmetric Multicomponent [3 + 3] Cyclization,” The Journal of Organic Chemistry 81, no. 17 (2016): 7898–907.
   PubMed Web of Science ®Google Scholar
• J.D. Sunderhaus and S.F. Martin, “Applications of Multicomponent Reactions to the Synthesis of Diverse Heterocyclic Scaffolds,” Chemistry (Weinheim an Der Bergstrasse, Germany) 15, no. 6 (2009): 1300–8.
   PubMed Web of Science ®Google Scholar
• M. Sapnakumari, B. Narayana, K.S. Shashidhara, and B. K. Sarojini, “Multicomponent Synthesis, Biological Evaluation and Molecular Docking of New Spiro-Oxindole Derivatives,” Journal of Taibah University for Science 11, no. 6 (2017): 1008–18.
   Web of Science ®Google Scholar
• J. Sh. Yua, and J. Zhou, “Organocatalytic Enantioselective Mukaiyama–Mannich Reaction of fluorinated Enol Silyl Ethers and Cyclic N-Sulfonyl Ketimines,” Organic Chemistry Frontiers 3, (2016): 298–303.
   Web of Science ®Google Scholar
• Y.C. Zhang, F. Jiang, and F. Shi, “Organocatalytic Asymmetric Synthesis of Indole-Based Chiral Heterocycles: Strategies, Reactions, and Outreach,” Accounts of Chemical Research 53, no. 2 (2020): 425–46.
   PubMed Web of Science ®Google Scholar
• Zh, Y. Cao, F. Zhou, and J. Zhou, “Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles,” Accounts of Chemical Research 51, no. 6 (2018): 1443–54.
   PubMed Web of Science ®Google Scholar
• F. Jiang, D. Zhao, X. Yang, F.R. Yuan, G.J. Mei, and F. Shi, “Catalyst-Controlled Chemoselective and Enantioselective Reactions of Tryptophols with Isatin-Derived Imines,” ACS Catalysis 7, no. 10 (2017): 6984–9.
   Web of Science ®Google Scholar
• G.J. Mei and F. Shi, “Indolylmethanols as Reactants in Catalytic Asymmetric Reactions,” The Journal of Organic Chemistry 82, no. 15 (2017): 7695–707.
   PubMed Web of Science ®Google Scholar
• Y.-L. Zhao, Z.-Y. Cao, X.-P. Zeng, J.-M. Shi, Y.-H. Yu, and J. Zhou, “Asymmetric Sequential Au(i)/chiral tertiary amine catalysis: an enone-formation/cyanosilylation sequence to synthesize optically active 3-alkenyloxindoles from diazooxindoles,” Chemical Communications (Cambridge, England) 52, no. 20 (2016): 3943–6.
   PubMed Web of Science ®Google Scholar
• G.J. Mei and F. Shi, “Catalytic Asymmetric Synthesis of Spirooxindoles: recent Developments,” Chemical Communications (Cambridge, England) 54, no. 50 (2018): 6607–21.
   PubMed Web of Science ®Google Scholar
• B. Yu, D.Q. Yu, and H.M. Liu, “Spirooxindoles: Promising Scaffolds for Anticancer Agents,” European Journal of Medicinal Chemistry 97, (2015): 673–98.
   PubMed Web of Science ®Google Scholar
• R. Ahdenov, A. Mohammadi, S. Taheri, P. Ghaderi, and M. Saadat, “An Efficient Synthesis for Some New Heterocyclic Compound-Fused Oxindole Derivatives,” Journal of Heterocyclic Chemistry 54, no. 1 (2017): 789–93.
   Web of Science ®Google Scholar
• M. Pourshab, S. Asghari, and M. Mohseni, “Synthesis and Antibacterial Evaluation of Novel Spiro,” Journal of Heterocyclic Chemistry 55, no. 1 (2018): 173–80.
   Web of Science ®Google Scholar
• K. Arya, D.S. Rawat, and H. Sasai, “Zeolite Supported Bronsted-Acid Ionic Liquids: An Eco Approach for Synthesis of Spiro[Indole-Pyrido[3,2-e]Thiazine] in Water under Ultrasonication,” Green Chemistry 14, no. 7 (2012): 1956–63.
   Web of Science ®Google Scholar
• L.-J. Zhou, Y.-C. Zhang, F. Jiang, G. He, J. Yan, H. Lu, S. Zhang, and F. Shi, “Enantioselective Construction of Cyclic Enaminone-Based 3-Substituted 3-Amino-2-Oxindole Scaffolds via Catalytic Asymmetric Additions of Isatin-Derived Imines,” Advanced Synthesis and Catalysis 358, no. 19 (2016): 3069–83.
   Web of Science ®Google Scholar
• G. Luppi, M. Monari, R.J. Corrêa, F.A. de Violante, A.C. Pinto, B. Kaptein, Q.B. Broxterman, S.J. Garden, and C. Tomasini, “The First Total Synthesis of (R)-Convolutamydine A,” Tetrahedron 62, no. 51 (2006): 12017–24.
   Web of Science ®Google Scholar
• W. Balk-Bindseil, E. Helmke, H. Weyland, and H. Laatsch, “Maremycin A and B, New Diketopiperazines from a Marine Streptomyces sp,” Liebigs Annalen 1995, no. 7 (1995): 1291–4.
   Google Scholar
• Y. Zhang, Z. Jun Li, H. S. Xu, Y. Zhang, and W. Wang, “Organocatalytic Asymmetric Henry Reaction of Isatins: Highly Enantioselective Synthesis of 3-Hydroxy-2-Oxindoles,” RSC Advances 1, no. 3 (2011): 389–92.
   Web of Science ®Google Scholar
• S. Mathusalini, T. Arasakumar, K. Lakshmi, C.-H. Lin, P.S. Mohan, M.G. Ramnath, and R. Thirugnanasampandan, “Synthesis and Biological Evaluation of New Spirooxindoles with Embedded Pharmacophores,” New Journal of Chemistry 40, no. 6 (2016): 5164–9.
   Web of Science ®Google Scholar
• S. Sadjadi, M. Heravi, and N. Nazari, “Isocyanide-Based Multcomponent Reactions to Synthesis of Heterocycles,” RSC Advances 6, no. 58 (2016): 53203–72.
   Web of Science ®Google Scholar
• A. Váradi, T. Palmer, R.N. Dardashti, and S. Majumdar, “Isocyanide-Based Multicomponent Reactions for the Synthesis of Heterocycles,” Molecules 21, no. 1 (2015): 19–22.
   Web of Science ®Google Scholar
• A. Shaabani, H. Rezayan, A. Sarvary, and A. Rahmati, “Isocyanide‐Catalyzed Reaction of Tetracyanoethylene and Activated 1,3‐Dicarbonyl CH‐Acid Compounds: A Rapid and Efficient Synthesis of Pyran Annulated Heterocyclic Systems,” Synthetic Communications 38, no. 2 (2008): 274–81.
   Web of Science ®Google Scholar
• R. Ghahremanzadeh, Z. Rashid, A.H. Zarnani, and H. Naeimi, “A Rapid and High Efficient Microwave Promoted Multicomponent 3 Domino Reaction for the Synthesis of Spirooxindole Derivatives,” Journal of Industrial and Engineering Chemistry 20, no. 6 (2014): 4076–84.
   Web of Science ®Google Scholar
• R. Ghahremanzadeh, Z. Rashid, A.H. Zarnani, and H. Naeimi, “Synthesis of Novel Spirooxindoles in Water by Using MnFe2o4 Nanoparticles as an Efficient Magnetically Recoverable and Reusable Catalyst,” Applied Catalysis A: General 467, (2013): 270–8.
   Web of Science ®Google Scholar
• R. Ghahremanzadeh, Z. Rashid, A.H. Zarnani, and H. Naeimi, “Manganese Ferrite Nanoparticle Catalyzed Tandem and Green Synthesis of Spirooxindoles,” RSC Advances 4, no. 82 (2014): 43661–70.
   Web of Science ®Google Scholar
• H. Naeimi, Z. Rashid, A.H. Zarnani, and R. Ghahremanzadeh, “An Efficient One-Pot Multicomponent Synthesis of 4-Aza-Podophyllotoxin Derivatives in Ionic Liquid,” Journal of Chemistry 2013 (2013): 1–9.
   Web of Science ®Google Scholar