240
Views
1
CrossRef citations to date
0
Altmetric
Research Articles

Cu(OAc)2.H2O Catalyzed C − H/C − N Bond Functionalization for the Synthesis of Isoquinoline Derivatives as Potential Antifungal Agent

, , & ORCID Icon
Pages 4404-4412 | Received 20 Mar 2020, Accepted 11 Feb 2021, Published online: 02 Mar 2021

Reference

  • M. Chrzanowska, and M. D. Rozwadowska, “Asymmetric Synthesis of Isoquinoline Alkaloids,” Chemical Reviews 104, no. 7 (2004): 3341–70.
  • P. Giri, and G. S. Kumar, “Isoquinoline Alkaloids and Their Binding with Polyadenylic Acid: Potential Basis of Therapeutic Action,” Mini Reviews in Medicinal Chemistry 10, no. 7 (2010): 568–77.
  • M. Iranshahy, R. J. Quinn, and M. Iranshahi, “Biologically Active Isoquinoline Alkaloids with Drug-like Properties from the Genus Corydalis,” RSC Advances 4 (2014): 15900–13.
  • R. Pingaew, S. Prachayasittikul, and S. Ruchirawat, “Synthesis, Cytotoxic and Antimalarial Activities of Benzoyl Thiosemicarbazone Analogs of Isoquinoline and Related Compounds,” Molecules 15, no. 2 (2010): 988–96.
  • N. W. Alcock, J. M. Brown, and G. I. Hulmes, “Synthesis and Resolution of 1-(2-Diphenylphosphino-1-Naphthyl)Isoquinoline; a PN Chelating Ligand for Asymmetric Catalysis,” Tetrahedron: Asymmetry 4, no. 4 (1993): 743–56.
  • C. W. Lim, O. Tissot, A. Mattison, M. W. Hooper, J. M. Brown, A. R. Cowley, D. I. Hulmes, and A. Blacker, “Practical Preparation and Resolution of 1-(2-Diphenylphosphino-1‘-Naphthyl)Isoquinoline: A Useful Ligand for Catalytic Asymmetric Synthesis,” Organic Process Research & Development 7, no. 3 (2003): 379–84.
  • B. A. Sweetman, H. Muller-Bunz, and P. J. Guiry, “Synthesis, Resolution, and Racemisation Studies of New Tridentate Ligands for Asymmetric Catalysis,” Tetrahedron Letters 46, no. 27 (2005): 4643–6.
  • F. Durola, J. P. Sauvage, and O. S. Wenger, “Sterically Non-Hindering Endocyclic Ligands of the Bi-Isoquinoline Family,” Chemical Communications 2, no. 2 (2006): 171–3.
  • S. J. Liu, Q. Zhao, R. F. Chen, Y. Deng, Q. L. Fan, F. Y. Li, L. H. Wang, C. H. Huang, and W. Huang, “ pi-Conjugated chelating polymers with Charged Iridium Complexes in the Backbones: Synthesis, Characterization, Energy Transfer, and Electrochemical Properties,” Chemistry (Weinheim an der Bergstrasse, Germany) 12, no. 16 (2006): 4351–61.
  • Q. Zhao, S. Liu, M. Shi, C. Wang, M. Yu, L. Li, F. Li, T. Yi, and C. Huang, “Series of New Cationic Iridium(III) Complexes with Tunable Emission Wavelength and Excited State Properties:  Structures, Theoretical Calculations, and Photophysical and Electrochemical properties,” Inorganic Chemistry 45, no. 16 (2006): 6152–60.
  • Łukasz Balewski, Franciszek Sączewski, Maria Gdaniec, Anita Kornicka, Karolina Cicha, and Aleksandra Jalińska, “Synthesis and Fluorescent Properties of Novel Isoquinoline Derivatives,” Molecules 24, no. 22 (2019): 4070.
  • Isravel Muthukrishnan, Vellaisamy Sridharan, and J. Carlos Menéndez, “Progress in the Chemistry of Tetrahydroquinolines,” Chemical Reviews 119, no. 8 (2019): 5057–191.
  • J. Wang, V. Jiang, B. Wang, and N. Zhang, “A Review on Analytical Methods for Natural Berberine Alkaloids,” Journal of Separation Science 42, no. 9 (2019): 1794–815.
  • G. Raghuram, V. Nagaraju, and C. M. Chandi, “Comprehensive Strategies for the Synthesis of Isoquinolines: Progress since 2008,” Advanced Synthesis and Catalysis 362 (2020): 4896–990.
  • Y. Yajun, G. Meng, Z. Yun-Hui, X. Wenlin, Z. Zhihua, and T. Zilong, “Efficient Synthesis of Isoquinoline and Its Derivatives: From Metal Сatalysts to Catalyst-Free Processes in Water,” Russian Journal of General Chemistry 90, no. 10 (2020): 2012–27.
  • A. Bischler, and B. Napieralski, “Zur Kenntniss Einer Neuen Isochinolinsynthese,”Berichte der deutschen chemischen Gesellschaft 26, no. 2 (1893): 1903–8.
  • A. Pictet, and T. Spengler, “Uber Die Bildung Von Isochinolin‐Derivaten Durch Einwirkung Von Methylal Auf Phenyl‐Athylamin, Phenyl‐Alanin Und Tyrosin,” Berichte der deutschen chemischen Gesellschaft 44, no. 3 (1911): 2030–6.
  • D. S. Deshmukh, N. Gangwar, and B. M. Bhanage, “Rapid and Atom Economic Synthesis of Isoquinolines and Isoquinolinones by C-H/N-N Activation Using Homogeneous Recyclable Ruthenium Catalyst in PEG Media,” European Journal of Organic Chemistry 2019, no. 18 (2019): 2919–27.
  • P. K. Mishra, S. Verma, M. Kumar, A. Kumar, and A. K. Verma, “Harnessing the Reactivity of ortho-Formyl-Arylketones: Base Promoted Regiospecific Synthesis of Functionalized Isoquinolines,” Chemical Communications (Cambridge, England) 55, no. 57 (2019): 8278–81.
  • L. Chao, X. Hui-Bei, Z. Jing, L. Man, and D. Lin, “Synthesis of Rhodium(III)-Catalyzed Isoquinoline Derivatives from Allyl Carbonates and Benzimidates with Hydrogen Evolution,” Organic & Biomolecular Chemistry 18, no. 7 (2020): 1412–6.
  • K. C. Jiang, L. Wang, Q. Chen, M. Y. He, M. G. Shen, and Z. H. Zhang, “Rh(III)-Catalyzed Synthesis of Isoquinolines from N-Hydroxyoximes and Alkynes in ϒ-Valerolactone,” Synthetic Communications 51, no. 1 (2021): 94–102.
  • S. L. Nakkalwar, H. M. Kasralikar, N. S. Kaminwar, S. B. Patwari, and V. B. Jadhav, “A Green Synthesis of Isoquinolines Using Ru(II)/PEG-400 as Homogeneous Recyclable Catalyst via C-H/N-N Bond Activation,” Indian Journal of Chemistry 59B (2020): 842–9.
  • D. S. Deshmukh, P. A. Yadav, and B. M. Bhanage, “Cp*Co(III)-Catalyzed Annulation of Azines by C-H/N-N Bond Activation for the Synthesis of Isoquinolines,” Organic & Biomolecular Chemistry 17, no. 14 (2019): 3489–96.
  • D. S. Deshmukh, and B. M. Bhanage, “Ruthenium-Catalyzed Annulation of N-Cbz Hydrazones via C–H/N–N Bond Activation for the Rapid Synthesis of Isoquinolines,” Synthesis 51, no. 12 (2019): 2506–I.21.
  • B. Nie, W. Wu, W. Zeng, Q. Ren, J. Zhang, Y. Zhang, and H. Jiang, “Synthesis of Isoquinoline Derivatives via Palladium‐Catalyzed C − H/C − N Bond Activation of N‐Acyl Hydrazones with α‐Substituted Vinyl Azides,” Advanced Synthesis & Catalysis 362, no. 6 (2020): 1362–9.
  • Q. Bing, F. Lili, W. Qi, G. Shan, S. Pengfei, C. Benfa, and Z. Jin, “Rh(III)-Catalyzed Synthesis of Isoquinolines Using the N-Cl Bond of N-Chloroimines as an Internal Oxidant,” Tetrahedron Letters 61, no. 16 (2020): 151771.
  • K. S. Singh, “Recent Advances in C–H Bond Functionalization with Ruthenium-Based Catalysts,” Catalysts 9, no. 2 (2019): 173.
  • J. G. Sun, X. Y. Zhang, H. Yang, P. Li, and B. Zhang, “Highly Regioselective Isoquinoline Synthesis via Nickel‐Catalyzed Iminoannulation of Alkynes at Room Temperature,” European Journal of Organic Chemistry 2018, no. 35 (2018): 4965–9.
  • Q. Z. Wan, Q. Kun, W. S. Cheng, S. Lei, Z. Wei, C. Dong-Mei, Z. Chen, and W. Xiu-Li, “Copper-Catalyzed Synthesis of Pyrazolo[5,1-a]Isoquinoline Derivatives from 2-Gem-Dipyrazolylvinyl Bromobenzenes,” New Journal of Chemistry 43 (2019): 10162–5.
  • T. V. V. Ramakrishna, and P. R. Sharp, “Naphthalenes, Isoquinolines and a Benzazocine from Zirconocene-Copper-Mediated Coupling of Benzocyclobutadiene with Nitriles and Alkynes,” Organic Letters 5, no. 6 (2003): 877–9.
  • G. Minghui, M. Xin, Z. Yang, D. Yuexia, S. Xuejun, T. Laijin, and C. Ziping, “Synthesis of 4-(1H-Isochromen-1-Yl)Isoquinolines through the Silver-Catalysed Homodimerization of Ortho-Alkynylarylaldehydes and Subsequent Condensation of the 1,5-Dicarbonyl Motif with NH3,” RSC Advances 9 (2019): 2703–7.
  • S. R. Mathapati, A. H. Jadhav, M. B. Swami, and J. K. Dawle, “Zinc Sulfamate Catalyzed Efficient Selective Synthesis of Benzimidazole Derivatives under Ambient Conditions,” Letters in Organic Chemistry 16, no. 9 (2019): 740–9.
  • S. R. Mathapati, D. Prasad, A. B. Atar, B. M. Nagaraja, J. K. Dawle, and J. K. Jadhav, “Phosphorofluoridic Acid as an Efficient Catalyst for One Pot Synthesis of Dihydropyrimidinones under Solvent Free and Ambient Condition,” Materials Today: Proceedings 9 (2019): 661–8.
  • S. R. Mathapati, J. F. Sakhare, M. B. Swami, and J. K. Dawle, “Application of Green Solvent in Synthesis of Thiophenytoins Using Aryl Thioureas,” Der Pharma Chemica 4 (2012): 2248–51.
  • V. B. Suryawanshi, K. I. Momin, J. K. Dawle, and S. R. Mathapati, “BCl3 Catalyzed, Solvent Free Protocol for the Synthesis of Dihydropyrano [3,2-b] Chromenediones,” Letters in Organic Chemistry 17 (2020): 1–7.
  • A. N. Vhadlure, R. V. Rohikar, G. A. Kulkarni, A. W. Suryavanshi, S. S. Mathkari, and S. R. Mathapati, “Synthesis and Spectral Characterization of Substituted Tetraphenylporphyrin Iron Chloride Complexes-Greener Approach,” International Journal of ChemTech Research 5 (2013): 522–7.
  • R. Dıaz-Torres, and S. Alvarez, “Coordinating Ability of Anions and Solvents towards Transition Metals and Lanthanides,” Dalton Transactions (Cambridge, England: 2003) 40, no. 40 (2011): 10742–50.
  • Y. N. Niu, Z. Yan, G. Gao, H. Wang, X. Shu, K. Ji, and Y. Liang, “Synthesis of Isoquinoline Derivatives via Ag-Catalyzed Cyclization of 2-Alkynyl Benzyl Azides,” The Journal of Organic Chemistry 74no. 7 (2009): 2893–6.
  • K. Shekarrao, P. P. Kaishap, S. Gogoi, and R. C. Boruah, “Efficient Synthesis of Isoquinolines and Pyridines via Copper(I)-Catalyzed Multi-Component Reaction,”RSC Advances 4no. 27 (2014): 14013–23.
  • H. Dai, C. X. Li, C. Yu, Z. Wang, H. Yan, and C. Lu, “Copper(II) Catalyzed Domino Synthesis of Quinoline Derivatives from Arylamines and Alkynes,”Organic Chemistry Frontiers 4no. 10 (2017): 2008–11.
  • S. C. Chuang, P. Gandeepan, and C. H. Cheng, “Synthesis of Isoquinolines via Rh(III)-Catalyzed C-H Activation Using Hydrazone as a New Oxidizing Directing Group,” Organic Letters 15, no. 22 (2013): 5750–3.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.