One pot synthesis of bis (dihydropyrimidinone) and tetrahydro-4H-chromenes derivatives using Ag₂O/GO/TiO₂ composite nanostructure

Reference

• Garg, B.; Ling, Y.-C. Versatilities of Graphene-Based Catalysts in Organic Transformations. Green Mater. 2013, 1, 47–61. DOI: 10.1680/gmat.12.00008.
   Web of Science ®Google Scholar
• Robinson, J. T.; Perkins, F. K.; Snow, E. S.; Wei, Z.; Sheehan, P. E. Reduced Graphene Oxide Molecular Sensors. Nano Lett. 2008, 8, 3137–3140. DOI: 10.1021/nl8013007.
   PubMed Web of Science ®Google Scholar
• Wang, H.; Hao, Q.; Yang, X.; Lu, L.; Wang, X. Graphene Oxide Doped Polyaniline for Supercapacitors. Electrochem. Commun. 2009, 11, 1158–1161. DOI: 10.1016/j.elecom.2009.03.036.
   Web of Science ®Google Scholar
• Zhang, L. L.; Zhao, X.; Stoller, M. D.; Zhu, Y.; Ji, H.; Murali, S.; Wu, Y.; Perales, S.; Clevenger, B.; Ruoff, R. S. Highly Conductive and Porous Activated Reduced Graphene Oxide Films for High-Power Supercapacitors. Nano Lett. 2012, 12, 1806–1812. DOI: 10.1021/nl203903z.
   PubMed Web of Science ®Google Scholar
• Dhakshinamoorthy, A.; Alvaro, M.; Concepción, P.; Fornés, V.; Garcia, H. Graphene Oxide as an Acid Catalyst for the Room Temperature Ring Opening of Epoxides. Chem. Commun. (Camb) 2012, 48, 5443–5445. DOI: 10.1039/c2cc31385e.
   PubMed Web of Science ®Google Scholar
• Dhopte, K. B.; Raut, D. S.; Patwardhan, A. V.; Nemade, P. R. Graphene Oxide as Recyclable Catalyst for One-Pot Synthesis of α-Aminophosphonates. Synth. Commun. 2015, 45, 778–788. DOI: 10.1080/00397911.2014.989447.
   Web of Science ®Google Scholar
• Dhopte, K. B.; Zambare, R. S.; Patwardhan, A. V.; Nemade, P. R. Role of Graphene Oxide as a Heterogeneous Acid Catalyst and Benign Oxidant for Synthesis of Benzimidazoles and Benzothiazoles. RSC Adv. 2016, 6, 8164–8172. DOI: 10.1039/C5RA19066E.
   Web of Science ®Google Scholar
• Islam, S. M.; Roy, A. S.; Dey, R. C.; Paul, S. Graphene Based Material as a Base Catalyst for Solvent Free Aldol Condensation and Knoevenagel Reaction at Room Temperature. J. Mol. Catal. Chem. 2014, 394, 66–73. DOI: 10.1016/j.molcata.2014.06.038.
   Web of Science ®Google Scholar
• Verma, S.; Mungse, H. P.; Kumar, N.; Choudhary, S.; Jain, S. L.; Sain, B.; Khatri, O. P. Graphene Oxide: An Efficient and Reusable Carbocatalyst for aza-Michael Addition of Amines to Activated Alkenes. Chem. Commun. (Camb) 2011, 47, 12673–12675. DOI: 10.1039/c1cc15230k.
   PubMed Web of Science ®Google Scholar
• Kadam, M. M.; Lokare, O. R.; Kireeti, K. V. M. K.; Gaikar, V. G.; Jha, N. Impact of the Degree of Functionalization of Graphene Oxide on the Electrochemical Charge Storage Property and Metal Ion Adsorption. RSC Adv. 2014, 4, 62737–62745. DOI: 10.1039/C4RA08862J.
   Web of Science ®Google Scholar
• Krishnamoorthy, K.; Veerapandian, M.; Yun, K.; Kim, S.-J. The Chemical and Structural Analysis of Graphene Oxide with Different Degrees of Oxidation. Carbon 2013, 53, 38–49. DOI: 10.1016/j.carbon.2012.10.013.
   Web of Science ®Google Scholar
• Yan, H.; Tao, X.; Yang, Z.; Li, K.; Yang, H.; Li, A.; Cheng, R. Effects of the Oxidation Degree of Graphene Oxide on the Adsorption of Methylene Blue. J. Hazard. Mater. 2014, 268, 191–198. DOI: 10.1016/j.jhazmat.2014.01.015.
   PubMed Web of Science ®Google Scholar
• Allaedini, G.; Tasirin, S. M.; Aminayi, P. Synthesis of Fe–Ni–Ce Trimetallic Catalyst Nanoparticles via Impregnation and co-Precipitation and Their Application to Dye Degradation. Chem. Pap. 2016, 70, 231–242.
   Web of Science ®Google Scholar
• Du, X.; Su, H.; Zhang, X. Metal-Organic Framework-Derived M (M = Fe, Ni, Zn, and Mo) Doped Co9S8 Nanoarrays as Efficient Electrocatalyst for Water Splitting: The Combination of Theoretical Calculation and Experiment. J. Catal. 2020, 383, 103–116. DOI: 10.1016/j.jcat.2020.01.015.
   Web of Science ®Google Scholar
• Ngcobo, M.; Nyamato, G. S.; Ojwach, S. O. Structural Elucidation of N^O (Ethylimino-Methyl)Phenol Fe(II) and Co(II) Complexes and Their Applications in Ethylene Oligomerization Catalysis. Mol. Catal. 2019, 478, 110590. DOI: 10.1016/j.mcat.2019.110590.
   Google Scholar
• Eckenhoff, W. T. Molecular Catalysts of Co, Ni, Fe, and Mo for Hydrogen Generation in Artificial Photosynthetic Systems. Coord. Chem. Rev. 2018, 373, 295–316. DOI: 10.1016/j.ccr.2017.11.002.
   Web of Science ®Google Scholar
• Adrienn, H.; Zoltán, H.; Ilona, V. Convenient One-Pot Heterogeneous Catalytic Method for the Preparation of 3,4- Dihydropyrimidin-2(1H)-Ones. Synth. Commun. 2006, 36, 129–136.
   Web of Science ®Google Scholar
• Sanjeev, P.; Gokavi, G. S. Heteropoly Acid Catalyzed Synthesis of 3, 4-Dihydropyrimidin-2 (1H)-Ones. Catal. Commun. 2007, 8, 279–284. DOI: 10.1016/j.catcom.2006.05.048.
   Web of Science ®Google Scholar
• (a) Nagarathnam, D.; Miao, S. W.; Lagu, B.; Harrell, M. C.; Vyas, K. P.; Gluchowski, C. J. Med. Chem.1999, 42, 4764–4777.
   PubMed Web of Science ®Google Scholar
  (b) Barrow, J. C.; Nantermet, P. G.; Nagarathnam, D.; Forray, C. J. Med. Chem. 2000, 43, 2703–2718.
   PubMed Web of Science ®Google Scholar
• Kappe, C. O. 100 Years of the Biginelli dihydropyrimidine synthesis. Tetrahedron 1993, 49, 6937–6963.
   Web of Science ®Google Scholar
• Grover, G. J.; Dzwonczyk, S.; McMullen, D. M.; Normandin, D. E.; Parham, C. S.; Sleph, P. G.; Moreland, S. Pharmacologic Profile of the Dihydropyrimidine Calcium Channel Blockers SQ 32,547 and SQ 32,926 [Correction of SQ 32,946]. J. Cardiovasc. Pharmacol. 1995, 26, 289–291. DOI: 10.1097/00005344-199508000-00015.
   PubMed Web of Science ®Google Scholar
• (a) Bose, D. S., Fatima, L., Mereyala, H. B.. Green Chemistry Approaches to the Synthesis of 5-Alkoxycarbonyl-4-aryl-3,4-Dihydropyrimidin-2(1H)-ones by a Three-Component Coupling of One-pot Condensation Reaction: Comparison of Ethanol, Water, and Solvent-Free Conditions. J. Org. Chem. 2003, 68, 587–590;
   PubMed Web of Science ®Google Scholar
  (b) Adib, M., Ghanbary, K., Mostofi, M., Ganjal, M. R. Molecules, 2006, 11, 649;
   PubMed Web of Science ®Google Scholar
  (c) Chari, M. A., Syamasundar, K. J. Mol. Catal. A. 2004, 221, 137. DOI: 10.1021/jo0205199.
   Web of Science ®Google Scholar
• Dallinger, D.; Gorobets, N. Y.; Kappe, C. O. High-Throughput Synthesis of N3-Acylated Dihydropyrimidines Combining Microwave-Assisted Synthesis and Scavenging Techniques. Org. Lett. 2003, 5, 1205–1208. DOI: 10.1021/ol034085v.
   PubMed Web of Science ®Google Scholar
• (a) Hu, E. H., Sidler, D. R., Dolling, U. H. Unprecedented Catalytic Three Component One-Pot Condensation Reaction: An Efficient Synthesis of 5-Alkoxycarbonyl- 4-aryl-3,4-dihydropyrimidin-2(1H)-ones, J. Org. Chem. 1998, 63, 3454–3457;
   Web of Science ®Google Scholar
  (b) Dondoni, A., Massi, A. Tetrahedron Lett. 2001, 42, 7975;
   Web of Science ®Google Scholar
  (c) Peng, J., Deng, Y. Tetrahedron Lett. 2001, 42, 5917. DOI: 10.1021/jo970846u.
   Web of Science ®Google Scholar
• (a) Yadav, J. S.; Subba Reddy, B. V.; Bhaskar Reddy, K.; Raj, K. S.; Prasad, A. R. Ultrasound-accelerated Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones with Ceric Ammonium Nitrate. J. Chem. Soc., Perkin Trans. 1, 2001, 1, 1939–1941;
   Google Scholar
  (b) Saxena, I.; Borah, D. C.; Sarma, J. C. Tetrahedron Lett., 2005, 46, 1159;
   Web of Science ®Google Scholar
  (c) Bussolari, J. C.; McDonnell, P. A. J Org Chem. 2000, 65, 6777. DOI: 10.1039/b102565c.
   PubMed Web of Science ®Google Scholar
• (a) Kappe, C. O.; Kumar, D.; Varma, R. S. Synthesis. 1999, 1799;
   Web of Science ®Google Scholar
  (b) Hu, E. H.; Sidler, D. R.; Dolling, U. H. J Org Chem. 1998, 63, 3454.
   Web of Science ®Google Scholar
• (a) Li, J. T.; Han, J. F.; Yang, J. H.; Li, T. S. Ultrasound Assisted Dehydrogenation of 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides. Ultrason Sonochem, 2011, 18, 119;
   Web of Science ®Google Scholar
  (b) Memarian, H. R.; Soleymani, M. Ultrason Sonochem. 2011, 18, 745–752. DOI: 10.1016/j.ultsonch.2010.10.006.
   Web of Science ®Google Scholar
• Alessandro, D.; Alessandro, M. Parallel Synthesis of Dihydropyrimidinones Using Yb(III)-Resin and Polymer-Supported Scavengers under Solvent-Free Conditions. A Green Chemistry Approach to the Biginelli Reaction. Tetrahedron Lett. 2001, 42, 7975.
   Web of Science ®Google Scholar
• Ranu, B. C.; Hajra, A.; Dey, S. S. A Practical and Green Approach towards Synthesis of Dihydropyrimidinones without Any Solvent or Catalyst. Org. Process Res. Dev. 2002, 6, 817–818. DOI: 10.1021/op0255478.
   Web of Science ®Google Scholar
• Xu, F.; Huang Lin, D. X.; Wang, Y. Highly Enantioselective Biginelli Reaction Catalyzed by SPINOL-Phosphoric Acids. Org. Biomol. Chem. 2012, 10, 4467– 4470. DOI: 10.1039/c2ob25663k.
   PubMed Web of Science ®Google Scholar
• Mirjalili, B. B. F.; *.; Zamani, L. Nano-Ticl4.SiO2: A Versatile and Efficient Catalyst for Synthesis of Dihydropyrimidones via Biginelli Condensation. S. Afr. J. Chem. 2014, 67, 21–26.
   Web of Science ®Google Scholar
• Girija, D.; Bhojya Naik, H. S.; Vinay Kumar, B.; Sudhamani, C. N.; Harish, K. N. Fe3O4 Nanoparticle Supported Ni (II) Complexes: A Magnetically Recoverable Catalyst for Biginelli Reaction. Arabian J. Chem. 2019, 12, 420–428. DOI: 10.1016/j.arabjc.2014.08.008.
   Web of Science ®Google Scholar
• Lima, C. G. S.; Silva, S.; Gonçalves, R. H.; Leite, E. R.; Schwab, R. S.; Corrêa, A. G.; Paixão, M. W. Highly Efficient and Magnetically Recoverable Niobium Nanocatalyst for the Multicomponent Biginelli Reaction. ChemCatChem. 2014, 6, 3455– 3463. DOI: 10.1002/cctc.201402689.
   Web of Science ®Google Scholar
• Safari, J.; *.; Zarnegar, Z. Biginelli Reaction on Fe3O4-MWCNT Nanocomposite: excellent Reactivity and Facile Recyclability of the Catalyst Combined with Ultrasound Irradiation. RSC Adv. 2013, 3, 17962–17967. DOI: 10.1039/c3ra43014f.
   Web of Science ®Google Scholar
• Mahato, B. N.; Krithiga, T. Mesoporous ZnO/AlSBA-15 Nanocomposite as an Efficient Catalyst for Synthesis of 3,4-Dihydropyrimidin-2(1H)-One via Biginelli Reaction and Their Biological Activity Study. Bull. Chem. React. Eng. Catal. 2019, 14, 634–645. DOI: 10.9767/bcrec.14.3.4469.634-645.
   Web of Science ®Google Scholar
• Zaheri, H. M.; Javanshir, S.; Hemmati, B.; Dolatkhah, Z.; Fardpour, M. Magnetic Core-shell Carrageenan moss/Fe3O4: A Polysaccharide-based Metallic Nanoparticles for Synthesis of Pyrimidinone Derivatives via Biginelli Reaction . Chem. Cent. J. 2018, 12, 108. DOI: 10.1186/s13065-018-0477-3.
   Google Scholar
• Bashti, A.; Kiasat, A. R. Biginelli Multicomponent Condensation Reaction Promoted by 4,4′-Bipyridinium Dichloride Ordered Mesoporous Silica Nanocomposite under Solvent Free Conditions. Org. Chem. Res. 2016, 2, 28–38.
   Google Scholar
• Maleki, A.; Niksefat, M.; Rahimi, J.; Hajizadeh, Z. Design and Preparation of Fe3O4@ PVA Polymeric Magnetic Nanocomposite Film and Surface Coating by Sulfonic Acid via in Situ Methods and Evaluation of Its Catalytic Performance in the Synthesis of Dihydropyrimidines. BMC Chem. 2019, 13, 19. DOI: 10.1186/s13065-019-0538-2.
   Web of Science ®Google Scholar
• Zarnegar, Z.; Safari, J. Magnetic Nanoparticles Supported Imidazolium-Based Ionic Liquids as Nanocatalyst in Microwave-Mediated Solvent-Free Biginelli Reaction. J. Nanopart. Res. 2014, 16, 2509. DOI: 10.1007/s11051-014-2509-9.
   Web of Science ®Google Scholar
• Dangolani, S. k.; Panahi,F.; Nourisefat, M.; Khalafi-Nezhad, A. 4-Dialkylaminopyridine Modified Magnetic Nanoparticles: As an Efficient Nano-Organocatalyst for One-Pot Synthesis of 2-Amino-4H-Chromene-3-Carbonitrile Derivatives in Water. RSC Adv. 2016, 6, )92316–92324. DOI: 10.1039/C6RA18078G.
   Web of Science ®Google Scholar
• Maleki, A.; Azadegan, s. Preparation and Characterization of Silica-Supported Magnetic Nanocatalyst and Application in the Synthesis of 2-Amino-4H-Chromene-3-Carbonitrile Derivatives. Inorg. Nano Metal Chem. 2017, 47, 917–924. DOI: 10.1080/24701556.2016.1241266.
   Web of Science ®Google Scholar
• Amirheidari, B.; Seifi, M.; Abaszadeh, M. Evaluation of Magnetically Recyclable nano-Fe3O4 as a Green Catalyst for the Synthesis of Mono- and Bistetrahydro-4H-Chromene and Mono and bis1,4-Dihydropyridine Derivatives. Res. Chem. Intermed. 2016, 42, 3413–3423. DOI: 10.1007/s11164-015-2220-1.
   Web of Science ®Google Scholar
• Mollashahi, E.; Nikraftar, M. Nano-SiO2 Catalyzed Three-Component Preparations of Pyrano[2,3-d]Pyrimidines, 4H-Chromenes, and Dihydropyrano[3,2-c]Chromenes. J. Saudi Chem. Soc. 2018, 22, 42–48. DOI: 10.1016/j.jscs.2017.06.003.
   Web of Science ®Google Scholar
• Mohammadzadeh, A.; Marjani, A. P.; Zamani, A. A Novel Biopolymer-Based Nanomagnetic Catalyst for the Synthesis of 4H-Pyran and Tetrahydro-4H-Chromene Derivatives. S. Afr. J. Chem. 2020, 73, 55–63.
   Web of Science ®Google Scholar
• Molaei, H. R.; Sadeghi, B. Microwave Assisted Multi-Component Synthesis of 4H-Chromene Derivatives by Nano-Coconut Shell-BF3 as a New Heterogeneous Catalyst. J. Appl. Chem. Res. 2019, 13, 85–96.
   Google Scholar
• Vessally, E.; Hassanpour, A.; Hosseinzadeh-Khanmiri, R.; Babazadeh, M.; Abolhasani, J. Green and Recyclable Sulfonated Graphene and Graphene Oxide Nanosheet Catalysts for the Syntheses of 3,4-Dihydropyrimidinones. Monatsh. Chem. 2017, 148, 321–326. volume DOI: 10.1007/s00706-016-1762-2.
   Web of Science ®Google Scholar
• Moitra, D.; Ghosh, B. K.; Chandel, M.; Ghosh, N. N. Synthesis of a BiFeO3 Nanowire-Reduced Graphene Oxide Based Magnetically Separable Nanocatalyst and Its Versatile Catalytic Activity towards Multiple Organic Reactions. RSC Adv. 2016, 6, 97941–98553. DOI: 10.1039/C6RA22077K.
   Web of Science ®Google Scholar
• Narayanan, D. P.; Gopalakrishnan, A.; Yaakob, Z.; Sugunan, S.; Narayanan, B. N. A Facile Synthesis of Clay – Graphene Oxide Nanocomposite Catalysts for Solvent Free Multicomponent Biginelli Reaction. Arabian J. Chem. 2020, 13, 318–334. DOI: 10.1016/j.arabjc.2017.04.011.
   Web of Science ®Google Scholar
• Achary, L. S. K.; Kumar, A.; Rout, L.; Kunapuli, S. V. S.; Dhaka, R. S.; Dash, P. Phosphate Functionalized Graphene Oxide with Enhanced Catalytic Activity for Biginelli Type Reaction under Microwave Condition. Chem. Eng. J. 2018, 331, 300–310. DOI: 10.1016/j.cej.2017.08.109.
   Web of Science ®Google Scholar
• Rostamizadeh, S.; Hemmasi, A.; Zekri, N. Magnetic Amine-Functionalized Graphene Oxide as a Novel and Recyclable Bifunctional Nanocatalyst for Solvent-Free Synthesis of Pyrano[3,2-c]Pyridine Derivatives. Nanochem. Res. 2017, 2, 29–41.
   Google Scholar
• Khosravi, K.; Khalaji, K.; Naserifar, S. Solvent‐ and Metal‐Free Oxidative Esterification of Aromatic Aldehydes Using Urea‐2,2‐Dihydroperoxypropane as a New Solid Oxidant. J. Chin. Chem. Soc. 2017, 64, 303–309. DOI: 10.1002/jccs.201600777.
   Web of Science ®Google Scholar
• Moosavi-Zare, A. R.; Zolfigol, M. A.; Khaledian, O.; Khakyzadeh, V.; Farahani, M. D.; Beyzavi, M. H.; Kruger, H. G. Tandem Knoevenagel–Michael–Cyclocondensation Reaction of Malononitrile, Various Aldehydes and 2-Naphthol over Acetic Acid Functionalized Ionic Liquid. Chem. Eng. J. 2014, 248, 122–127. DOI: 10.1016/j.cej.2014.03.035.
   Web of Science ®Google Scholar
• Nyankson, E.; Adjasoo, J.; Kwame Efavi, J.; Yaya, A.; Manu, G.; Kingsford, A.; Yeboah Abrokwah, R. Synthesis and Kinetic Adsorption Characteristics of Zeolite/CeO2 Nanocomposite. Scient. Afr. 2020, 7, e00257. DOI: 10.1016/j.sciaf.2019.e00257.
   Google Scholar
• Mohammadi, M. K.; Gutiérrez, A.; Hayati, P.; Mohammadi, K.; Rezaei, R. Diverse Structural Assemblies and Influence in the Morphology of Different Parameters in a Series of 0D and 1D Mercury(II) Metal-Organic Coordination Complexes by the Sonochemical Process. Polyhedron 2019, 160, 20–34. DOI: 10.1016/j.poly.2018.12.016.
   Web of Science ®Google Scholar
• Mohammadi, M. K. Solvent-Free Synthesis of Oxovanadium (V) complexes with Isatin Base Schiff Ligands. Inorg. Nano-Metal Chem. 2017, 47, 1323–1327. VOL. NO. DOI: 10.1080/24701556.2017.1284096.
   Web of Science ®Google Scholar
• Xiao, L.; Youji, L.; Feitai, C.; Peng, X.; Ming, L. Facile Synthesis of Mesoporous Titanium Dioxide Doped by Ag-Coated Graphene with Enhanced Visible-Light Photocatalytic Performance for Methylene Blue Degradation. RSC Adv. 2017, 7, 25314–25324. DOI: 10.1039/C7RA02198D.
   Web of Science ®Google Scholar
• Kumar, D.; Reddy, V. B.; Sharad, S.; Dube, U.; Kapur, S. 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 . Eur. J. Med. Chem. 2009, 44, 3805–3809. DOI: 10.1016/j.ejmech.2009.04.017.
   PubMed Web of Science ®Google Scholar
• Taheri Hatkehlouei, S. F.; Mirza, B.; Soleimani- Amiri, S. Solvent-Free One-Pot Synthesis of Diverse Dihydropyrimidinones/Tetrahydropyrimidinones Using Biginelli Reaction Catalyzed by Fe3O4@C@OSO3H. Polycycl. Arom. Compd. 2020, DOI: 10.1080/10406638.2020.1781203.
   Web of Science ®Google Scholar
• Sayyahi, S.; Behvandi, M. Highly Efficient Multicomponent Biginelli’s Synthesis of 3,4-dihydropyrimidin2(1H)-Ones Catalyzed by Al-MCM-41 under Solvent-Free Conditions. Iran J. Catal. 2015, 5, 119–122.
   Web of Science ®Google Scholar
• Zhang, Y.; Wang, B.; Zhang, X.; Huang, J.; Liu, C. An Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones and Thiones Catalyzed by a Novel Brønsted Acidic Ionic Liquid under Solvent-Free Conditions. Molecules 2015, 20, 3811–3820. DOI: 10.3390/molecules20033811.
   PubMed Web of Science ®Google Scholar
• Javanshir, S.; Safari, M.; Dekamin, M. G. A Facile and Green Three-Component Synthesis of2-Amino-3-Cyano-7-Hydroxy-4H-Chromenes on Grinding. Sci. Iran. 2014, 21, 742–747.
   Web of Science ®Google Scholar
• Kumar, A.; Rao, M. S. An Expeditious and Greener One-Pot Synthesis of 4Hchromenes Catalyzed by Ba(OTf)2 in PEG-Water. Green Chem. Lett. Rev. 2012, 5, 283–290. DOI: 10.1080/17518253.2011.623683.
   Web of Science ®Google Scholar