Fe3O4@SiO2/Kit-6 as a Magnetic Nano-Catalyst for the Synthesis of New Coumarin Fused Pyrrole Derivatives

Subject Areas : Polymer

Elham Sadr ¹ , Hossein Anaraki-Ardakani ² , Soheil Sayyahi ³ , Farzaneh Hosseini ⁴

1 - Department of Chemistry, Mahshahr Branch, Islamic Azad University, Mahshahr, Iran
2 - Department of Chemistry, Mahshahr Branch, Islamic Azad University, Mahshahr, Iran
3 - Department of Chemistry, Mahshahr Branch, Islamic Azad University, Mahshahr, Iran
4 - Department of Chemistry, Mahshahr Branch, Islamic Azad University, Mahshahr, Iran

Received: 2023-12-13 Accepted : 2023-12-13 Published : 2023-10-01

Keywords:

Abstract :

A series of new coumarin fused pyrrole derivatives were successfully synthesized through a one-pot multi-component reaction between 4-aminocoumarin, aryl glyoxals, and amides (thioacetamide) in the presence of Fe3O4@SiO2/Kit-6 in ethanol under reflux conditions. Further advantages to this synthesis include excellent yields, mild reaction conditions, atom economy, environment-friendly, magnetically reusable catalyst, and no need for chromatographic separations.

References:

1. Murray R, McKinnie S, Moore B, George Meroterpenoid natural products from Streptomycesbacteria – the evolution of chemoenzymatic syntheses. Nat Prod Rep. 2020;,37: 1334-1366


2. Lacy A, O'kennedy R. Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. Current pharmaceutical design. 2004;10(30):3797-811.


3. Patil AD, Freyer AJ, Eggleston DS, Haltiwanger RC, Bean MF, Taylor PB, et al. The inophyllums, novel inhibitors of HIV-1 reverse transcriptase isolated from the Malaysian tree, Calophyllum inophyllum Linn. Journal of medicinal chemistry. 1993;36(26):4131-8.


4. Guilet D, Hélesbeux J-J, Séraphin D, Sévenet T, Richomme P, Bruneton J. Novel Cytotoxic 4-Phenylfuranocoumarins from Calophyllum d ispar. Journal of natural products. 2001;64(5):563-8.


5. Emami S, Dadashpour S. Current developments of coumarin-based anti-cancer agents in medicinal chemistry. European Journal of Medicinal Chemistry. 2015;102:611-30.


6. Keri RS, Sasidhar B, Nagaraja BM, Santos MA. Recent progress in the drug development of coumarin derivatives as potent antituberculosis agents. European journal of medicinal chemistry. 2015;100:257-69.


7. Jones G, Gilow HM, Low J. Regioselective photoaddition of pyrroles and aliphatic carbonyl compounds. A new synthesis of 3 (4)-substituted pyrroles. The Journal of Organic Chemistry. 1979;44(16):2949-51.


8. DL B. Boyce CW. Labroli MA. Sehon CA. Jin Q. J Am Chem Soc. 1999;121:54.


9. Yang X, Jing L, Chen Z. An efficient method for one-pot synthesis of 3-alkoxy-substituted chromeno [4, 3-b] pyrrol-4 (1 H)-one derivatives. Chemistry of Heterocyclic Compounds. 2018;54:1065-9.


10. Trost BM. The atom economy—a search for synthetic efficiency. Science. 1991;254(5037):1471-7.


11. Bienayme H, Hulme C, Oddon G, Schmidt P. Chem. sEur. J. 2000;6:3321.


12. Heidarpour M, Kiani M, Anaraki-Ardakani H, Rezaei P, Ghaleh SP, Ahmadi R, et al. New magnetic nanocomposite Fe₃O₄@ Saponin/Cu (II) as an effective recyclable catalyst for the synthesis of aminoalkylnaphthols via Betti reaction. Steroids. 2022:109170.


13. Orru RV, de Greef M. Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds. Synthesis. 2003;2003(10):1471-99.


14. Climent MJ, Corma A, Iborra S. Homogeneous and heterogeneous catalysts for multicomponent reactions. RSC advances. 2012;2(1):16-58.


15. Astruc D, Lu F, Aranzaes JR. Nanoparticles as recyclable catalysts: the frontier between homogeneous and heterogeneous catalysis. Angewandte Chemie International Edition. 2005;44(48):7852-72.


16. Lim CW, Lee IS. Magnetically recyclable nanocatalyst systems for the organic reactions. Nano Today. 2010;5(5):412-34.


17. Zheng X, Luo S, Zhang L, Cheng J-P. Magnetic nanoparticle supported ionic liquid catalysts for CO 2 cycloaddition reactions. Green Chemistry. 2009;11(4):455-8.


18. Ma C, Shao H, Zhan S, Hou P, Zhang X, Chai Y, et al. Bi-phase dispersible Fe₃O₄@ Au core–shell multifunctional nanoparticles: Synthesis, characterization and properties. Composite Interfaces. 2019;26(6):537-49.


19. Rossi LM, Costa NJ, Silva FP, Wojcieszak R. Magnetic nanomaterials in catalysis: advanced catalysts for magnetic separation and beyond. Green Chemistry. 2014;16(6):2906-33.


20. Koli RR, Phadatare MR, Sinha BB, Sakate DM, Ghule AV, Ghodake GS, et al. Gram bean extract-mediated synthesis of Fe3O4 nanoparticles for tuning the magneto-structural properties that influence the hyperthermia performance. Journal of the Taiwan Institute of Chemical Engineers. 2019;95:357-68.


21. Gill CS, Price BA, Jones CW. Sulfonic acid-functionalized silica-coated magnetic nanoparticle catalysts. Journal of Catalysis. 2007;251(1):145-52.


22. Samiei Z, Soleimani-Amiri S, Azizi Z. Fe ₃ O ₄@ C@ OSO ₃ H as an efficient, recyclable magnetic nanocatalyst in Pechmann condensation: green synthesis, characterization, and theoretical study. Molecular Diversity. 2021;25:67-86.


23. Zeinali S, Fekri LZ, Nikpassand M, Varma RS. Greener syntheses of coumarin derivatives using magnetic nanocatalysts: recent advances. Topics in Current Chemistry. 2023;381(1):1.


24. Nikpassand M, Fekri LZ, Sahrapeima S, Shariati S. Synthesis of bis coumarinyl methanes using Fe3O4@ SiO2@ KIT-6 as an efficient and reusable catalyst. Letters in Organic Chemistry. 2016;13(8):578-84.


25. Fekri LZ, Maleki R. KIT‐6 Mesoporous silica‐coated magnetite nanoparticles: A highly efficient and easily reusable catalyst for the synthesis of benzo [d] imidazole derivatives. Journal of Heterocyclic Chemistry. 2017;54(2):1167-71.


26. Nikpassand M, Fekri LZ, Nabatzadeh M. Fe3O4@ SiO2@ KIT-6 as an Efficient and Reusable Catalyst for the Synthesis of Novel Derivatives of 3, 3'-((Aryl-1-phenyl-1H-pyrazol-4-yl) methylene) bis (1H-indole). Combinatorial Chemistry & High Throughput Screening. 2017;20(6):533-8.


27. Nikpassand M, Fekri LZ, Sanagou S. Green synthesis of 2-hydrazonyl-4-phenylthiazoles using KIT-6 mesoporous silica coated magnetite nanoparticles. Dyes and Pigments. 2017;136:140-4.


28. Abdolmohammadi S, Shariati S, Fard NE, Samani A. Aqueous‐Mediated green synthesis of novel spiro [indole‐quinazoline] derivatives using kit‐6 mesoporous silica coated Fe3O4 nanoparticles as catalyst. Journal of Heterocyclic Chemistry. 2020;57(7):2729-37.


29. Heidarpour M, Anaraki‐Ardakani H, Hasanzadeh N, Rayatzadeh A. Efficient synthesis of β‐aminoketones catalyzed by Fe₃O₄@ quillaja sapogenin/Ni (II) as a novel magnetic nano‐catalyst. Applied Organometallic Chemistry. 2020;34(10):e5834.


30. Kiani M, Anaraki-Ardakani H, Hasanzadeh N, Rayatzadeh A. Fe₃O₄@ saponin/Cd: a novel magnetic nano-catalyst for the synthesis of β-aminoketone derivatives. Journal of the Iranian Chemical Society. 2020;17(9):2243-56.


31. Khabazipour M, Shariati S, Safa F. SBA and KIT-6 mesoporous silica magnetite nanoparticles: Synthesis and characterization. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry. 2016;46(5):759-65.


32. Saha M, Pradhan K, Das AR. Facile and eco-friendly synthesis of chromeno [4, 3-b] pyrrol-4 (1H)-one derivatives applying magnetically recoverable nano crystalline CuFe₂O₄ involving a domino three-component reaction in aqueous media. RSC advances. 2016;6(60):55033-8.


33. Khalili B, Jajarmi P, Eftekhari-Sis B, Hashemi MM. Novel one-pot, three-component synthesis of new 2-alkyl-5-aryl-(1 H)-pyrrole-4-ol in water. The Journal of organic chemistry. 2008;73(6):2090-5.