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Research Articles

Green Approach of Solvent- and Catalyst Free Synthesis of Bis(indolyl)methanes under Visible Light Irradiation

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Pages 1761-1769 | Received 23 Jun 2020, Accepted 29 Jul 2020, Published online: 06 Aug 2020

References

  • (a) L. F. Tietze, “Domino Reactions in Organic Synthesis,” Chemical Reviews 96, no. 1 (1996): 115–136; (b) A. Dömling, and I. Ugi. “Multicomponent Reactions with Isocyanides,” Angewandte Chemie (International ed. in English) 39, no. 18 (2000): 3168–3210.
  • (a) L. Weber, “Multi-component Reactions and Evolutionary Chemistry,” Drug Discovery Today 7, no. 2 (2002) 143–147; (b) A. Dömling, “Recent Advances in Isocyanide-Based Multicomponent Chemistry,” Current Opinion in Chemical Biology 6, no. 3 (2002): 306–313.
  • (a) F. Bossert, H. Meyer, and E. Wehinger, “4-Aryldihydropyridines, A New Class of Highly Active Calcium Antagonists,” Angewandte Chemie (International ed. in English) 20, no. 9 (1981): 762–769; (b) H. Nakayama, and Y. Kasoaka, “Chemical Identification of Binding Sites for Calcium Channel Antagonists,” Heterocycles 42 (1996): 901–909.
  • (a) T. Godfraid, R. Miller, and M. Wibo, “Calcium Antagonism and Calcium Entry Blockade,” Pharmacological Reviews 38, no. 4 (1986): 321–416; (b) A. Sausins, and G. Duburs, “Synthesis of 1,4-Dihydropyridines by Cyclocondensation Reactions,” Heterocycles 27 (1988): 269–289; (c) P. P. Mager, R. A. Coburn, A. J. Solo, D. J. Triggle, and H. Rothe, “QSAR, Diagnostic Statistics and Molecular Modeling of 1,4-Dihydropyridine Calcium Antagonists: A Difficult Road Ahead,” Drug Design & Discovery 8, no. 4 (1992): 273–289; (d) R. Mannhold, B. Jablonka, W. Voigdt, K. Schoenafinger, and K. Schravan, “Calcium- and Calmodulinantagonism of Elnadipine Derivatives: Compaeative SAR,” European Journal of Medicinal Chemistry 27, no. 3 (1992): 229–235.
  • S.-J. Ji, S.-Y. Wang, Y. Zhang, and T.-P. Loh, “Facile Synthesis of Bis(Indolyl)Methanes Using Catalytic Amount of Iodine at Room Temperature under Solvent - Free Conditions,” Tetrahedron 60, no. 9 (2004): 2051–5.
  • A. K. Chakraborti, S. R. Roy, D. Kumar, and P. Chopra, “Catalytic Application of Room Temperature Ionic Liquids: [Bmim][MeSO4] as a Recyclable Catalyst for Synthesis of Bis(Indolyl)Methanes. Ion-Fishing by MALDI-TOF-TOF MS and MS/MS Studies to Probe the Proposed Mechanistic Model of Catalysis,” Green Chemistry 10, no. 10 (2008): 1111–8.
  • S. Y. Wang, and S. J. Ji, “Facile Synthesis of Bis(Indolyl)Methanes Catalyzed by Ferric Dodecyl Sulfonate [Fe(DS)3] in Water at Room Temperature,” Synthetic Communications 38, no. 8 (2008): 1291–8.
  • C. C. Silveira, S. R. Mendes, F. M. Líbero, E. J. Lenardão, and G. Perin, “Glycerin and CeCl3·7H2O: A New and Efficient Recyclable Medium for the Synthesis of Bis(Indolyl)Methanes,” Tetrahedron Letters 50, no. 44 (2009): 6060–3.
  • C. Praveen, Y. Wilson Sagayaraj, and P. T. Perumal, “Gold(I)-Catalyzed Sequential Cycloisomerization/Bis-Addition of o-Ethynylanilines: An Efficient Access to Bis(Indolyl)Methanes and Di(Indolyl)Indolin-2-Ones,” Tetrahedron Letters 50, no. 6 (2009): 644–7.
  • M. A. Naik, D. Sachdev, and A. Dubey, “Sulfonic Acid Functionalized Mesoporous SBA-15 for One-Pot Synthesis of Substituted Aryl-14H-Dibenzo Xanthenes and Bis(Indolyl)Methanes,” Catalysis Communications 11, no. 14 (2010): 1148–53.
  • C. Huo, C. Sun, C. Wang, X. Jia, and W. Chang, “Triphenylphosphine-m-Sulfonate/Carbon Tetrabromide as an Efficient and Easily Recoverable Catalyst System for Friedel - Crafts Alkylation of Indoles with Carbonyl Compounds or Acetals,” ACS Sustainable Chemistry & Engineering 1, no. 5 (2013): 549–53.
  • K. R. Naidu, S. I. Khalivulla, S. Rasheed, S. Fakurazi, P. Arulselvan, O. Lasekan, and F. Abas, “Synthesis of Bisindolylmethanes and Their Cytotoxicity Properties,” International Journal of Molecular Sciences 14, no. 1 (2013): 1843–53.
  • N. Azizi, L. Torkian, and M. R. Saidi, “Highly Efficient Synthesis of Bis(Indolyl)Methanes in Water,” Journal of Molecular Catalysis A: Chemical 275, no. 1–2 (2007): 109–12.
  • M. Karthik, A. Tripathi, N. Gupta, M. Palanichamy, and V. Murugesan, “Zeolite Catalyzed Electrophilic Substitution Reaction of Indoles with Aldehydes: Synthesis of Bis(Indolyl)Methanes,” Catalysis Communications 5, no. 7 (2004): 371–5.
  • H. Hikawa, H. Suzuki, Y. Yokoyama, and I. Azumaya, “Mechanistic Studies for Synthesis of Bis(Indolyl)Methanes: Pd-Catalyzed C-H Activation of Indole-Carboxylic Acids with Benzyl Alcohols in Water,” Catalysts 3, no. 2 (2013): 486–500.
  • H. Hikawa, and Y. Yokoyama, “Pd-Catalyzed C-H Activation in Water: Synthesis of Bis(Indolyl)Methanes from Indoles and Benzyl Alcohols,” RSC Advances 3, no. 4 (2013): 1061–4.
  • (a) V. Klusa, “Cerebrocrast Neuroprotectant, Cognition Enhancer,” Drugs of the Future 20, no. 2 (1995): 135–138; (b) R. G. Bretzel, C. C. Bollen, E. Maeser, and K. F. Federlin, “Nephroprotective Effects of Nitrendipine in Hypertensive Type I and Type II Diabetic Patients,” American Journal of Kidney Diseases 21, no. 6 Suppl 3 (1993): 53–64; (c) R. G. Retzel, C. C. Bollen, E. Maeser, and K. F. Federlin, “Trombodipine Platelet Aggregation Inhibitor Antithrombotic,” Drugs of the Future 17 (1992): 465–468; (d) R. Boer, and V. Gekeler, “Chemosensitizers in Tumor Therapy: New Compounds Promise Better Efficacy,” Drugs of the Future 20 (1995): 499–509.
  • H. L. Davis, and T. E. Davis, “Daunorubicin and Adriamycin in Cancer Treatment: An Analysis of Their Roles and Limitations,” Cancer Treatment Reports 63, no. 5 (1979): 809–15.
  • I. Pastan, and M. M. N. Gottesman, “ Multiple-drug resistance in human cancer,” The New England Journal of Medicine 316, no. 22 (1987): 1388–93.
  • Hirokazu Tanabe, Shigeyuki Tasaka, Hiromasa Ohmori, Noriaki Gomi, Yoshiyuki Sasaki, Toshiki Machida, Mayumi Iino, Akira Kiue, Seiji Naito, and Michihiko Kuwano, “Newly Synthesized Dihydropyridine Derivatives as Modulators of P-Glycoprotein-Mediated Multidrug Resistance,” Bioorganic & Medicinal Chemistry 6, no. 11 (1998): 2219–27.
  • P. Anastas, and J. Warner, Green Chemistry: Theory and Practice (Oxford, UK: Oxford University Press, 1998).
  • P. T. Anastas, and T. C. Williamson, Eds., Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes (Oxford, UK: Oxford University Press, 1998).
  • M. Lancaster, Green Chemistry: An Introductory Text (Cambridge, UK: Royal Society of Chemistry, 2002).
  • J. Banothu, R. Gali, R. Velpula, R. Bavantula, and P. A. Crooks, “An Eco-Friendly Improved Protocol for the Synthesis of Bis(3-Indolyl)Methanes Using Poly(4-Vinylpyridinium)Hydrogen Sulfate as Efficient, Heterogeneous, and Recyclable Solid Acid Catalyst,” ISRN Organic Chemistry 2013 (2013): 616932–5. https://doi.org/http://dx.doi.org/10.1155/2013/616932.
  • M. N. K. Reddi, C. H. Sung, and K. Il, “Synthesis of Bis(Indolyl)Methanes Using Hyper-Cross-Linked Polyaromatic Spheres Decorated with Bromomethyl Groups as Efficient and Recyclable Catalysts,” ACS Omega 3 (2018): 2242–53.
  • Y. Wang, R. Sang, Y. Zheng, L. Guo, M. Guan, and Y. Wu, “Graphene Oxide: An Efficient Recyclable Solid Acid for the Synthesis of Bis(Indolyl)Methanes from Aldehydes and Indoles in Water,” Catalysis Communications 89 (2017): 138–42.
  • Carla Grosso, Ana Lúcia Cardoso, Américo Lemos, João Varela, Maria João Rodrigues, Luísa Custódio, Luísa Barreira, and Teresa M. V. D. Pinho e Melo, “Novel Approach to Bis(Indolyl)Methanes: De Novo Synthesis of 1-Hydroxyiminomethyl Derivatives with anti-Cancer Properties,” European Journal of Medicinal Chemistry 93, (2015): 9–15.
  • M. L. Deb, B. Deka, P. J. Saikia, and P. K. Baruah, “Base-Promoted Three-Component Cascade Approach to Unsymmetrical Bis(Indolyl)Methanes,” Tetrahedron Letters 58, no. 20 (2017): 1999–2003.
  • J. Kothandapani, A. Ganesan, and S. S. Ganesan, “Magnetically Separable Sulfonic Acid Catalysed One-Pot Synthesis of Diverse Indole Derivatives,” Tetrahedron Letters 56, no. 41 (2015): 5568–72.
  • Y. Fu, Z. Lu, K. Fang, X. He, H. Xu, and Y. Hu, “Enzymatic Approach to Cascade Synthesis of Bis(Indolyl)Methanes in Pure Water,” RSC Advances 10, no. 18 (2020): 10848–53.
  • Z. Wu, G. Wang, S. Yuan, D. Wu, W. Liu, B. Ma, S. Bi, H. Zhan, and X. Chen, “Synthesis of Bis(Indolyl)Methanes under Dry Grinding Conditions, Promoted by a Lewis Acid-Surfactant-SiO2-Combined Nanocatalyst,” Green Chemistry 21, no. 13 (2019): 3542–6.

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