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Research Articles

Per-6-NH2-β-CD as Supramolecular Host and Reusable Aminocyclodextrin Promoted Solvent-Free Synthesis of 2-Amino-4H-Chromene Scaffolds at Room Temperature

Pages 6417-6428 | Received 11 Feb 2021, Accepted 14 Sep 2021, Published online: 01 Oct 2021

References

  • F. Mohamadpour, “Carboxymethyl Cellulose (CMC) as a Recyclable Green Catalyst Promoted Eco-Friendly Protocol for the Solvent-Free Synthesis of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Dione Derivatives,” Polycyclic Aromatic Compounds (2020), 1–12. doi: 10.1080/10406638.2020.1768412.
  • F. Mohamadpour, “Supramolecular β-Cyclodextrin as a Biodegradable and Reusable Catalyst Promoted Environmentally Friendly Synthesis of Pyrano[2,3-d]Pyrimidine Scaffolds via Tandem Knoevenagel–Michael–Cyclocondensation Reaction in Aqueous Media,” Polycyclic Aromatic Compounds (2020), 1–10. doi: 10.1080/10406638.2020.1852274.
  • F. Mohamadpour, “New Role for Photoexcited Organic Dye, Na2 Eosin Y via the Direct Hydrogen Atom Transfer (HAT) Process in Photochemical Visible-Light-Induced Synthesis of Spiroacenaphthylenes and 1H-Pyrazolo [1,2-b] Phthalazine-5,10-Diones under Air Atmosphere,” Dyes and Pigments 194, (2021), 109628.
  • F. Mohamadpour, “Imin-Based Synthesis of Polyfunctionalized Dihydro-2-Oxypyrroles Catalyzed by Glycine Amino Acid via Tandem Michael–Mannich Cyclocondensation Reaction under Ambient Temperature,” Research on Chemical Intermediates 46, no. 3 (2020): 1931–40.
  • L. Bonsignore, G. Loy, D. Secci, and A. Calignano, “Synthesis and Pharmacological Activity of 2-Oxo-(2H) 1-Benzopyran-3-Carboxamide Derivatives,” European Journal of Medicinal Chemistry 28, no. 6 (1993): 517–20.
  • A. Martínez-Grau, and J. Marco, “Friedländer Reaction on 2-Amino-3-Cyano-4H-Pyrans: Synthesis of Derivatives of 4H-Pyran [2,3-b] Quinoline, New Tacrine Analogues,” Bioorganic & Medicinal Chemistry Letters 7, no. 24 (1997): 3165–70.
  • H. G. Kathrotiya, and M. P. Patel, “Microwave-Assisted Synthesis of 30-Indolyl Substituted 4H-Chromenes Catalyzed by DMAP and Their Antimicrobial Activity,” Medicinal Chemistry Research 21, no. 11 (2012): 3406–16.
  • L. Alvey, S. Prado, B. Saint-Joanis, S. Michel, M. Koch, S. T. Cole, F. Tillequin, and Y. L. Janin, “Diversity-Oriented Synthesis of Furo[3,2-f]Chromanes with Antimycobacterial Activity,” European Journal of Medicinal Chemistry 44, no. 6 (2009): 2497–505.
  • D. O. Moon, K. C. Kim, C. Y. Jin, M. H. Han, C. Park, K. J. Lee, Y. M. Park, Y. H. Choi, and G. Y. Kim, “Inhibitory Effects of Eicosapentaenoic Acid on Lipopolysaccharide-Induced Activation in BV2 Microglia,” International Immunopharmacology 7, no. 2 (2007): 222–9.
  • D. Kumar, V. B. Reddy, S. Sharad, U. Dube, and S. Kapur, “A Facile One-Pot Green Synthesis and Antibacterial Activity of 2-Amino-4H-Pyrans and 2-Amino-5-oxo-5,6,7,8-Tetrahydro-4H-Chromenes,” European Journal of Medicinal Chemistry 44, no. 9 (2009): 3805–9.
  • T. Symeonidis, M. Chamilos, D. J. Hadjipavlou-Litina, M. Kallitsakis, and K. E. Litinas, “Synthesis of Hydroxycoumarins and Hydroxybenzo[f]- or [h]Coumarins as Lipid Peroxidation Inhibitors,” Bioorganic & Medicinal Chemistry Letters 19, no. 4 (2009): 1139–42.
  • T. Narender, and S. Gupta, “A Convenient and Biogenetic Type Synthesis of Few Naturally Occurring Chromeno Dihydrochalcones and Their in Vitro Antileishmanial Activity,” Bioorganic & Medicinal Chemistry Letters 19, (2009), 3913–6.
  • M. Rueping, E. Sugiono, and E. Merino, “Asymmetric Organocatalysis: An Efficient Enantioselective Access to Benzopyranes and Chromenes,” Chemistry (Weinheim an Der Bergstrasse, Germany) 14, no. 21 (2008): 6329–32.
  • M. T. Flavin, J. D. Rizzo, A. Khilevich, A. Kucherenko, A. K. Sheinkman, V. Vilaychack, L. Lin, W. Chen, E. M. Greenwood, T. Pengsuparp, et al. “Synthesis, Chromatographic Resolution, and anti-Human Immunodeficiency Virus Activity of (+/-)-Calanolide A and its Enantiomers,” Journal of Medicinal Chemistry 39, no. 6 (1996): 1303–13.
  • Fathy M. Abdelrazek, Peter Metz, and Ebtehal K. Farrag, “Synthesis and Molluscicidal Activity of 5-Oxo-5,6,7,8-Tetrahydro-4H-Chromene Derivatives,” Archiv Der Pharmazie 337, no. 9 (2004): 482–5.
  • P. K. Paliwal, S. R. Jetti, and S. Jain, “Green Approach towards the Facile Synthesis of Dihydropyrano(c)Chromene and Pyrano[2,3-d]-Pyrimidine Derivatives and Their Biological Evaluation,” Medicinal Chemistry Research 22, no. 6 (2013): 2984–90.
  • S. X. Cai, J. Drewe, and W. Kemnitzer, “Discovery of 4-aryl-4H-Chromenes as Potent Apoptosis Inducers Using a Cell- and Caspase-Based Anti-Cancer Screening Apoptosis Program (ASAP): SAR Studies and the Identification of Novel Vascular Disrupting Agents,” Anti-Cancer Agents in Medicinal Chemistry 9, no. 4 (2009): 437–56.
  • J. L. Wang, D. X. Liu, Z. J. Zhang, S. M. Shan, X. B. Han, S. M. Srinivasula, C. M. Croce, E. S. Alnemri, and Z. W. Huang, “Structure-Based Discovery of an Organic Compound that Binds Bcl-2 Protein and Induces Apoptosis of Tumor Cells,” Proceedings of the National Academy of Sciences of the United States of America 97, no. 13 (2000): 7124–9.
  • T. H. V. Huynh, B. Abrahamsen, K. K. Madsen, A. Gonzalez- Franquesa, A. A. Jensen, and L. Bunch, “Design, Synthesis and Pharmacological Characterization of Coumarin-Based Fluorescent Analogs of Excitatory Amino Acid Transporter Subtype 1 Selective Inhibitors, UCPH-101 and UCPH-102,” Bioorganic & Medicinal Chemistry 20, no. 23 (2012): 6831–9.
  • B. Datta, and M. A. Pasha, “Glycine Catalyzed Convenient Synthesis of 2-Amino-4H-Chromenes in Aqueous Medium under Sonic Condition,” Ultrasonics Sonochemistry 19, no. 4 (2012): 725–8.
  • G. T. Pawar, R. R. Magar, and M. K. Lande, “Mesolite: An Efficient Heterogeneous Catalyst for One-Pot Synthesis of 2-Amino-4H-Chromenes,” Polycyclic Aromatic Compounds 38, no. 1 (2018): 75–84. http://doi.org/10.1080/10406638.2016.1159584.
  • M. G. Dekamin, and M. Eslami, “Highly Efficient Organocatalytic Synthesis of Diverse and Densely Functionalized 2-Amino-3-Cyano-4H-Pyrans under Mechanochemical Ball Milling,” Green Chemistry 16, no. 12 (2014): 4914–21.
  • B. Eshtehardian, M. Rouhani, and Z. Mirjafary, “Green Protocol for Synthesis of MgFe2O4 Nanoparticles and Study of Their Activity as an Efficient Catalyst for the Synthesis of Chromene and Pyran Derivatives under Ultrasound Irradiation,” Journal of the Iranian Chemical Society 17, no. 2 (2020): 469–81.
  • S. Hosseinzadeh-Baghan, M. Mirzaei, H. Eshtiagh-Hosseini, V. Zadsirjan, M. M. Heravi, and J. T. Mague, “An Inorganic–Organic Hybrid Material Based on a Keggin Type Polyoxometalate@Dysprosium as an Effective and Green Catalyst in the Synthesis of 2-Amino-4H-Chromenes via Multicomponent Reactions,” Applied Organometallic Chemistry 34, no. 9 (2020): e5793–816.
  • J. Albadi, and A. Mansournezhad, “Aqua-Mediated Multicomponent Synthesis of Various 4H-Pyran Derivatives Catalyzed by Poly (4-Vinylpyridine)-Supported Copper Iodide Nanoparticle Catalyst,” Research on Chemical Intermediates 42, no. 6 (2016): 5739–52.
  • S. M. Baghbanian, N. Rezaei, and H. Tashakkorian, “Nanozeolite Clinoptilolite as a Highly Efficient Heterogeneous Catalyst for the Synthesis of Various 2-Amino-4H-Chromene Derivatives in Aqueous Media,” Green Chemistry 15, no. 12 (2013): 3446–58.
  • K. Kantharaju, and S. Y. Khatavi, “Microwave Accelerated Synthesis of 2-Amino-4H-Chromenes Catalyzed by WELFSA: A Green Protocol,” ChemistrySelect 3, no. 18 (2018): 5016–24.
  • S. K. Kundu, J. Mondal, and A. Bhaumik, “Tungstic Acid Functionalized Mesoporous SBA-15: A Novel Heterogeneous Catalyst for Facile One-Pot Synthesis of 2-Amino-4H-Chromenes in Aqueous Medium,” Dalton Transactions (Cambridge, England : 2003) 42, no. 29 (2013): 10515–24.
  • M. Saikia, and L. Saikia, “Sulfonic Acid-Functionalized MIL-101(Cr) as a Highly Efficient Heterogeneous Catalyst for One-Pot Synthesis of 2-Amino-4H-Chromenes in Aqueous Medium,” RSC Advances 6, no. 19 (2016): 15846–53.
  • M. A. Shaikh, M. Farooqui, and S. Abed, “Novel Task‑Specific Ionic Liquid [Et2NH(CH2)2CO2H][AcO] as a Robust Catalyst for the Efficient Synthesis of Some Pyran‑Annulated Scaffolds under Solvent-Free Conditions,” Research on Chemical Intermediates 45, no. 3 (2019): 1595–617.
  • M. A. Zolfigol, M. Yarie, and S. Baghery, “Application of {[4,4′-BPyH][C(CN)3]2} as a Bifunctional Nanostructured Molten Salt Catalyst for the Preparation of 2-Amino-4Hchromene Derivatives under Solvent-Free and Benign Conditions,” Synlett 27, no. 9 (2016): 1418–22.
  • D. Sing. Raghuvanshi, and K. Nand. Singh, “An Expeditious Synthesis of Novel Pyranopyridine Derivatives Involving Chromenes under Controlled Microwave Irradiation,” Arkivoc 2010, no. 10 (2010): 305–17.
  • S. R. Kale, S. S. Kahandal, A. S. Burange, M. B. Gawande, and R. V. Jayaram, “A Benign Synthesis of 2-Amino-4H-Chromene in Aqueous Medium Using Hydrotalcite (HT) as a Heterogeneous Base Catalyst,” Catalysis Science & Technology 3, no. 8 (2013): 2050–6.
  • J. Safari, Z. Zarnegar, and M. Heydarian, “Magnetic Fe3O4 Nanoparticles as Efficient and Reusable Catalyst for the Green Synthesis of 2-Amino-4H-Chromene in Aqueous Media,” Bulletin of the Chemical Society of Japan 85, no. 12 (2012): 1332–8.
  • B. Sadeghi, E. Arabian, and E. Akbarzadeh, “Nano-cellulose-OTiCl3 as a Green and Efficient Catalyst for One-Pot Synthesis of 2-Amino-7-Hydroxy-4-Aryl-4H-Chromene-3-Carbonitrile,” Inorganic and Nano-Metal Chemistry 50, no. 12 (2020): 1207–12.
  • P. R. Ashton, R. KöNiger, J. Fraser. Stoddart, D. Alker, and V. D. Harding, “Amino Acid Derivatives of β-Cyclodextrin,” The Journal of Organic Chemistry 61, no. 3 (1996): 903–8.
  • I. Abulkalam Azath, P. Puthiaraj, and K. Pitchumani, “One-Pot Multicomponent Solvent-Free Synthesis of 2-Amino-4H-Benzo[b]Pyrans Catalyzed by per-6-Amino-β-Cyclodextrin,”ACS Sustainable Chemistry & Engineering 1, no. 1 (2013): 174–9.
  • Y. Sonoda, F. Hirayama, H. Arima, Y. Yamaguchi, W. Saenger, and K. Uekama, “Selective Crystallization of the Metastable Form IV Polymorph of Tolbutamide in the Presence of 2,6-Di-O-Methyl-β-Cyclodextrin in Aqueous Solution,” Crystal Growth & Design 6, no. 5 (2006): 1181–5.
  • K. Kanagaraj, and K. Pitchumani, “Per-6-Amino-β-Cyclodextrin as a Chiral Base Catalyst Promoting One-Pot Asymmetric Synthesis of 2-Aryl-2,3-Dihydro-4-Quinolones,” The Journal of Organic Chemistry 78, no. 2 (2013): 744–51.
  • K. Kanagaraj, and K. Pitchumani, “Solvent-Free Multicomponent Synthesis of Pyranopyrazoles: Per-6-Amino-b-Cyclodextrin as a Remarkable Catalyst and Host,” Tetrahedron Letters 51, no. 25 (2010): 3312–6.
  • F. Mohamadpour, “Synthesis of Pyran-Annulated Heterocyclic Systems Catalyzed by Theophylline as a Green and Bio-Based Catalyst,” Polycyclic Aromatic Compounds 41, no. 1 (2021): 160–72.
  • F. Mohamadpour, “A New Role for Photoexcited Na2 Eosin Y as Direct Hydrogen Atom Transfer (HAT) Photocatalyst in Photochemical Synthesis of Dihydropyrano[2,3-c]Pyrazole Scaffolds Promoted by Visible Light Irradiation under Air Atmosphere,” Journal of Photochemistry and Photobiology A: Chemistry 418, (2021), 113428.
  • F. Mohamadpour, “Glycine as a Green Catalyst for the Preparation of Xanthenes,” Organic Preparations and Procedures International 53, no. 1 (2021): 59–67.

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