Experimental and theoretical studies on SPION@glutathione catalyzed synthesis of indolyl chromene, indolo xanthene, and pyrimido[4,5-b]quinoline

References

• Hernández, J. G.; Juaristi, E. Recent Efforts Directed to the Development of More Sustainable Asymmetric Organocatalysis. Chem. Commun. 2012, 48(44), 5396–5409. DOI: 10.1039/c2cc30951c.
   PubMed Web of Science ®Google Scholar
• Jarvo, E. R.; Miller, S. J. Amino Acids and Peptides as Asymmetric Organocatalysts. Tetrahedron. 2002, 58(13), 2481–2495. DOI: 10.1016/S0040-4020(02)00122-9.
   Web of Science ®Google Scholar
• List, B. Introduction: Organocatalysis. Chem. Rev. 2007, 107(12), 5413–5415. DOI: 10.1021/cr078412e.
   Web of Science ®Google Scholar
• Singh, N. G.; Nongrum, R.; Kathing, C.; Rani, J. W. S.; Nongkhlaw, R. Bakers’ Yeast: An Environment Benign Catalyst for the One-Pot Synthesis of Indolyl Chromenes and Bisindolyl Alkanes. Green Chem. Lett. Rev. 2014, 7(2), 137–144. DOI: 10.1080/17518253.2014.902506.
   Web of Science ®Google Scholar
• Khalafi-Nezhad, A.; Nourisefat, M.; Panahi, F. Trimethylsilyl Iodide as a Multifunctional Agent in the One-Pot Synthesis of 9-(1H-Indol-3-yl)xanthen-4-(9H)-ones from O-Methyl Protected Salicylaldehydes, Indoles, and β-Dicarbonyl Compounds. Synthesis (Stuttg). 2014, 46(15), 2071–2078. DOI: 10.1055/s-0033-1338633.
   Google Scholar
• Kohno, K.; Nakagawa, K.; Yahagi, T.; Choi, J.; Yasuda, H.; Sakakura, T. Fe(OTf) 3 -Catalyzed Addition of sp C−H Bonds to Olefins. J. Am. Chem. Soc. 2009, 131(8), 2784–2785. DOI: 10.1021/ja8090593.
   PubMed Web of Science ®Google Scholar
• Babu, G.; Sridhar, N.; Perumal, P. T. A Convenient Method of Synthesis of Bis -Indolylmethanes: Indium Trichloride Catalyzed Reactions of Indole with Aldehydes and Schiff’s Bases. Synth. Commun. 2000, 30(9), 1609–1614. DOI: 10.1080/00397910008087197.
   Web of Science ®Google Scholar
• Naganaboina, R. T.; Peddinti, R. K. BF 3 · Etherate-Mediated Friedel–Crafts Arylation of 2-Hydroxy-1,4-benzoxazines: Synthesis of 2-Aryl-1,4-benzoxazine Derivatives. J. Org. Chem. 2013, 78(24), 12819–12824. DOI: 10.1021/jo402254n.
   PubMed Web of Science ®Google Scholar
• Litvinov, Y. M.; Mortikov, V. Y.; Shestopalov, A. M. Versatile Three-Component Procedure for Combinatorial Synthesis of 2-Aminospiro[(3′H)-indol-3′,4-(4H)-pyrans]. J. Comb. Chem. 2008, 10(5), 741–745. DOI: 10.1021/cc800093q.
   PubMedGoogle Scholar
• Cheng, T.; Zhang, D.; Li, H.; Liu, G. Magnetically Recoverable Nanoparticles as Efficient Catalysts for Organic Transformations in Aqueous Medium. Green Chem. 2014, 16(7), 3401–3427. DOI: 10.1039/C4GC00458B.
   Web of Science ®Google Scholar
• Varma, R. S. Journey on Greener Pathways: From the Use of Alternate Energy Inputs and Benign Reaction Media to Sustainable Applications of Nano-Catalysts in Synthesis and Environmental Remediation. Green Chem. 2014, 16(4), 2027–2041. DOI: 10.1039/c3gc42640h.
   Web of Science ®Google Scholar
• Singh, N. G.; Lily, M.; Devi, S. P.; Rahman, N.; Ahmed, A.; Chandra, A. K.; Nongkhlaw, R. Synthetic, Mechanistic and Kinetic Studies on the Organo-Nanocatalyzed Synthesis of Oxygen and Nitrogen Containing Spiro Compounds Under Ultrasonic Conditions. Green Chem. 2016, 18(15), 4216–4227. DOI: 10.1039/C6GC00724D.
   Web of Science ®Google Scholar
• Pompella, A.; Visvikis, A.; Paolicchi, A.; Tata, V. De; Casini, A. F. The Changing Faces of Glutathione, a Cellular Protagonist. Biochem. Pharmacol. 2003, 66(8), 1499–1503. DOI: 10.1016/S0006-2952(03)00504-5.
   PubMed Web of Science ®Google Scholar
• Deponte, M. Glutathione Catalysis and the Reaction Mechanisms of Glutathione-Dependent Enzymes. Biochim. Biophys. Acta - Gen. Subj. 2013, 1830(5), 3217–3266. DOI: 10.1016/j.bbagen.2012.09.018.
   PubMed Web of Science ®Google Scholar
• Kathrotiya, H. G.; Patel, M. P. Microwave-Assisted Synthesis of 3′-Indolyl Substituted 4H-Chromenes Catalyzed by DMAP and their Antimicrobial Activity. Med. Chem. Res. 2012, 21(11), 3406–3416. DOI: 10.1007/s00044-011-9861-4.
   Web of Science ®Google Scholar
• Shanthi, G.; Perumal, P. T. An Eco-Friendly Synthesis of 2-Aminochromenes and Indolyl Chromenes Catalyzed by InCl3 in Aqueous Media. Tetrahedron Lett. 2007, 48(38), 6785–6789. DOI: 10.1016/j.tetlet.2007.07.102.
   Web of Science ®Google Scholar
• Polshettiwar, V.; Varma, R. S. Nano-Organocatalyst: Magnetically Retrievable Ferrite-Anchored Glutathione for Microwave-Assisted Paal–Knorr Reaction, Aza-Michael Addition, and Pyrazole Synthesis. Tetrahedron. 2010, 66(5), 1091–1097. DOI: 10.1016/j.tet.2009.11.015.
   Web of Science ®Google Scholar
• Baruwati, B.; Polshettiwar, V.; Varma, R. S. Glutathione Promoted Expeditious Green Synthesis of Silver Nanoparticles in Water Using Microwaves. Green Chem. 2009, 11(7), 926. DOI: 10.1039/b902184a.
   Web of Science ®Google Scholar
• Polshettiwar, V.; Baruwati, B.; Varma, R. S. Magnetic Nanoparticle-Supported Glutathione: A Conceptually Sustainable Organocatalyst. Chem. Commun. 2009, 1(14), 1837. DOI: 10.1039/b900784a.
   Web of Science ®Google Scholar
• Becke, A. D. Density‐Functional Thermochemistry. III. The Role of Exact Exchange. J. Chem. Phys. 1993, 98(7), 5648–5652. DOI: 10.1063/1.464913.
   Web of Science ®Google Scholar
• Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density. Phys. Rev. B. 1988, 37(2), 785–789. DOI: 10.1103/PhysRevB.37.785.
   PubMed Web of Science ®Google Scholar
• Reddi, Y.; Sunoj, R. B. Origin of Stereoselectivity in a Chiral N-Heterocyclic Carbene-Catalyzed Desymmetrization of Substituted Cyclohexyl 1,3-Diketones. Org. Lett. 2012, 14(11), 2810–2813. DOI: 10.1021/ol301036u.
   PubMed Web of Science ®Google Scholar
• Zolfigol, M. A.; Afsharnadery, F.; Baghery, S.; Salehzadeh, S.; Maleki, F. Catalytic Applications of {[HMIM]C(NO2)3}: As a Nano Ionic Liquid for the Synthesis of Pyrazole Derivatives Under Green Conditions and a Mechanistic Investigation with a New Approach. RSC Adv. 2015, 5(92), 75555–75568. DOI: 10.1039/C5RA16289K.
   Web of Science ®Google Scholar
• Ma, Z.; Guan, Y.; Liu, H. Superparamagnetic Silica Nanoparticles with Immobilized Metal Affinity Ligands for Protein Adsorption. J. Magn. Magn. Mater. 2006, 301(2), 469–477. DOI: 10.1016/j.jmmm.2005.07.027.
   Web of Science ®Google Scholar