GO@dopamine-Cu as a Green Nanocatalyst for the Efficient Synthesis of Fully Substituted Dihydrofuran-2(5H)-ones

Abstract

A new nanocatalyst graphene oxide@dopamine-Cu was synthesized, and its structure was characterized by fourier transform infrared (FT-IR), X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), Energy Dispersive X-ray Spectrometry (EDX), and thermogravimetric analysis – differential thermal analysis (TGA-DTA) techniques. The three-component one-pot reaction between an arylamine, aromatic aldehyde, and acetylenic carboxylate was achieved and formed methyl 5-oxo-2-aryl-4-(arylamino)-2,5-dihydrofuran-3-carboxylate derivatives (4) in the presence of the catalytic amount of graphene oxide@dopamine-Cu nanocatalyst in high yield. Molecular structures of products were characterized by FT-IR, 1H, 13C nuclear magnetic resonance (NMR), and Mass spectroscopy techniques. Representatively, the mass fragmentation of 4a was discussed, and the structure was confirmed. Easy reaction, high performance, and easy catalyst recyclability are the main advantages of this work. This nanocatalyst is recycled up to five successive runs.

Keywords

• Dihydrofuran-2(5H)-one
• Dimethyl acetylenedicarboxylate
• Green synthesis
• Graphene oxide
• Dopamine
• Copper

References

1. 1. Subodh S, Prakash K, Masram DT. A reversible chromogenic covalent organic polymer for gas sensing applications. Dalton Transactions. 2020;49(4):1007–10. Available from: .
2. 2. Yadav D, Awasthi SK. An unsymmetrical covalent organic polymer for catalytic amide synthesis. Dalton Transactions. 2020;49(1):179–86. Available from: .
3. 3. Subodh, Prakash K, Masram DT. Chromogenic covalent organic polymer-based microspheres as solid-state gas sensor. Journal of Material Chemistry C. 2020;8(27):9201–4. Available from: .
4. 4. Presolski S, Pumera M. Graphene Oxide: Carbocatalyst or Reagent? Angewandte Chemie, International Edition. 2018 Dec 17;57(51):16713–5. Available from: .
5. 5. Zhang M, Liu YH, Shang ZR, Hu HC, Zhang ZH. Supported molybdenum on graphene oxide/Fe3O4: An efficient, magnetically separable catalyst for one-pot construction of spiro-oxindole dihydropyridines in deep eutectic solvent under microwave irradiation. Catalysis Communications. 2017 Jan;88:39–44. Available from: .
6. 6. Subodh, Mogha NK, Chaudhary K, Kumar G, Masram DT. Fur-Imine-Functionalized Graphene Oxide-Immobilized Copper Oxide Nanoparticle Catalyst for the Synthesis of Xanthene Derivatives. ACS Omega. 2018 Nov 30;3(11):16377–85. Available from: .
7. 7. Yadav D, Awasthi SK. A Pd NP-confined novel covalent organic polymer for catalytic applications. New Journal of Chemistry. 2020;44(4):1320–5. Available from: .
8. 8. Yadav D, Awasthi SK. A Pd confined hierarchically conjugated covalent organic polymer for hydrogenation of nitroaromatics: catalysis, kinetics, thermodynamics and mechanism. Green Chemistry. 2020;22(13):4295–303. Available from: .

9. 9. Subodh, Prakash K, Masram DT. Silver Nanoparticles Immobilized Covalent Organic Microspheres for Hydrogenation of Nitroaromatics with Intriguing Catalytic Activity. ACS Applied Polymeric Materials. 2021 Jan 8;3(1):310–8. Available from: .
10. 10. Chaudhary K, Subodh, Prakash K, Mogha NK, Masram DT. Fruit waste (Pulp) decorated CuO NFs as promising platform for enhanced catalytic response and its peroxidase mimics evaluation. Arabian Journal of Chemistry. 2020 Apr;13(4):4869–81. Available from: .
11. 11. Stankovich S, Dikin DA, Piner RD, Kohlhaas KA, Kleinhammes A, Jia Y, et al. Synthesis of graphene-based nanosheets via chemical reduction of exfoliated graphite oxide. Carbon. 2007 Jun;45(7):1558–65. Available from: .
12. 12. Dreyer DR, Todd AD, Bielawski CW. Harnessing the chemistry of graphene oxide. Chemical Society Reviews. 2014 Jul 7;43(15):5288-301. Available from: .
13. 13. Compton OC, Nguyen ST. Graphene Oxide, Highly Reduced Graphene Oxide, and Graphene: Versatile Building Blocks for Carbon‐Based Materials. Small. 2010 Mar 22;6(6):711–23. Available from: .
14. 14. Noori S, Ghorbani-Vaghei R, Azadbakht R, Karamshahi Z, Koolivand M. Graphene-oxide/schiff base N2O4 ligand-palladium: A new catalyst for the synthesis of furan derivatives. Journal of Molecular Structure. 2022 Feb;1250:131849. Available from: .
15. 15. Dömling A. Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry. Chemical Reviews. 2006 Jan 1;106(1):17–89. Available from: .
16. 16. Pour M, Špulák M, Buchta V, Kubanová P, Vopršalová M, Wsól V, et al. 3-Phenyl-5-acyloxymethyl-2 H , 5H -furan-2-ones: Synthesis and Biological Activity of a Novel Group of Potential Antifungal Drugs. Journal of Medicinal Chemistry. 2001 Aug 1;44(17):2701–6. Available from: .
17. 17. Wu J, Cheng Y, Zhao X, Liu X, Sun W, Ren H, et al. Antibacterial activity and biological performance of a novel antibacterial coating containing a halogenated furanone compound loaded poly(L-lactic acid) nanoparticles on microarc-oxidized titanium. International Journal of Nanomedicine. 2015 Jan;727. Available from: .
18. 18. Tejedor D, García-Tellado F. Chemo-differentiating ABB′ multicomponent reactions. Privileged building blocks. Chemical Society Reviews. 2007;36(3):484–91. Available from: .
19. 19. Shirzaei M, Mollashahi E, Taher Maghsoodlou M, Lashkari M. Novel synthesis of silica-coated magnetic nano-particles based on acidic ionic liquid, as a highly efficient catalyst for three component system leads to furans derivatives. Journal of the Saudi Chemical Society. 2020 Feb;24(2):216–22. Available from: .
20. 20. Weber V. Novel 4,5-Diaryl-3-hydroxy-2(5H)-furanones as Anti-Oxidants and Anti-Inflammatory Agents. Bioorganic & Medicinal Chemistry. 2002 Jun;10(6):1647–58. Available from: .
21. 21. Lattmann E, Ayuko WO, Kinchinaton D, Langley CA, Singh H, Karimi L, et al. Synthesis and evaluation of 5-arylated 2(5 H )-furanones and 2-arylated pyridazin-3(2 H )-ones as anti-cancer agents. Journal of Pharmacy and Pharmacology. 2010 Feb 18;55(9):1259–65. Available from: .
22. 22. El-Tombary AA, Abdel-Ghany YS, Belal ASF, Shams El-Dine SA, Soliman FSG. Synthesis of some substituted furan-2(5H)-ones and derived quinoxalinones as potential anti-microbial and anti-cancer agents. Medicinal Chemistry Research. 2011 Sep;20(7):865–76. Available from: .
23. 23. Lipshutz BH. Five-membered heteroaromatic rings as intermediates in organic synthesis. Chemical Reviews. 1986;86(5):795–819.
24. 24. Mortensen DS, Rodriguez AL, Carlson KE, Sun J, Katzenellenbogen BS, Katzenellenbogen JA. Synthesis and Biological Evaluation of a Novel Series of Furans: Ligands Selective for Estrogen Receptor α. Journal of Medicinal Chemistry. 2001 Nov 1;44(23):3838–48. Available from: .
25. 25. Bassetti M, D’Annibale A, Fanfoni A, Minissi F. Synthesis of α,β-Unsaturated 4,5-Disubstituted γ-Lactones via Ring-Closing Metathesis Catalyzed by the First-Generation Grubbs’ Catalyst. Organic Letters. 2005 Apr 1;7(9):1805–8. Available from: .
26. 26. Bock I, Bornowski H, Ranft A, Theis H. New aspects in the synthesis of mono- and dialkylfurans. Tetrahedron. 1990 Jan;46(4):1199–210. Available from: .
27. 27. Takahashi S, Kubota A, Nakata T. Total synthesis of muconin. Tetrahedron Letters. 2002 Nov;43(48):8661–4. Available from: .
28. 28. Bandurraga MM, Fenical W, Donovan SF, Clardy J. Pseudopterolide, an irregular diterpenoid with unusual cytotoxic properties from the Caribbean sea whip Pseudopterogorgia acerosa (Pallas)(Gorgonacea). Journal of the American Chemical Society. 1982;104(23):6463–5.
29. 29. Padakanti S, Pal M, Yeleswarapu KR. An improved and practical synthesis of 5,5-dimethyl-3-(2-propoxy)-4-(4-methanesulfonylphenyl)-2-(5H)-furanone (DFP—a selective inhibitor of cyclooxygenase-2). Tetrahedron. 2003 Sep;59(40):7915–20. Available from: .
30. 30. Lee ES, Park BC, Paek SH, Lee YS, Basnet A, Jin DQ, et al. Potent Analgesic and Anti-inflammatory Activities of 1-Furan-2-yl-3-pyridin-2-yl-propenone with Gastric Ulcer Sparing Effect. Biological & Pharmaceutical Bulletin. 2006;29(2):361–4. Available from: .
31. 31. Rossi R, Bellina F, Biagetti M, Mannina L. Stereocontrolled synthesis of lissoclinolide by sequential transition metal-catalyzed lactonization/cross-coupling reactions. Tetrahedron Letters. 1998 Oct;39(42):7799–802. Available from: .
32. 32. Levy L. 5H-Furan-2-ones from fungal cultures of Aporpium caryae. Phytochemistry. 2003 Jan;62(2):239–43. Available from: .
33. 33. Hofnung M, Quillardet P, Michel V, Touati E. Genotoxicity of 2-nitro-7-methoxy-naphtho[2,1-b]furan (R7000): A case study with some considerations on nitrofurantoin and nifuroxazide. Research in Microbiology. 2002 Sep;153(7):427–34. Available from: .
34. 34. Wahab Khan M, Jahangir Alam M, Rashid MA, Chowdhury R. A new structural alternative in benzo[b]furans for antimicrobial activity. Bioorganic & Medicinal Chemistry. 2005 Aug;13(16):4796–805. Available from: .
35. 35. Pour M, Špulák M, Balšánek V, Kuneš J, Kubanová P, Buchta V. Synthesis and structure–antifungal activity Relationships of 3-Aryl-5-alkyl-2,5-dihydrofuran-2-ones and Their Carbanalogues: further refinement of tentative pharmacophore group. Bioorganic & Medicinal Chemistry. 2003 Jul;11(13):2843–66. Available from: .
36. 36. Shafiee MRM, Mansoor SS, Ghashang M, Fazlinia A. Preparation of 3,4,5-substituted furan-2(5H)-ones using aluminum hydrogen sulfate as an efficient catalyst. Comptes Rendus Chimie. 2014 Feb;17(2):131–4. Available from: .
37. 37. Karamshahi Z, Ghorbani‐Vaghei R. Efficient synthesis of multiply substituted furans using BF@Propyl/dopamine/Pd as a green catalyst. Applied Organometallic Chemistry. 2020 Apr;34(4):e5530. Available from: .
38. 38. Wipf P, Rahman LT, Rector SR. A General Strategy for Five-Membered Heterocycle Synthesis by Cycloelimination of Alkynyl Ketones, Amides, and Thioamides. The Journal of Organic Chemistry. 1998;63(21):7132–3.
39. 39. Golonka AN, Schindler CS. Iron(III) chloride-catalyzed synthesis of 3-carboxy-2,5-disubstituted furans from γ-alkynyl aryl- and alkylketones. Tetrahedron. 2017 Jul;73(29):4109–14. Available from: .
40. 40. Kangani M, Hazeri N, Maghsoodlou MT. Synthesis of pyrrole and furan derivatives in the presence of lactic acid as a catalyst. Journal of the Saudi Chemical Society. 2017 Feb;21(2):160–4. Available from: .