Exploring the Untapped Catalytic Application of a ZnO/CuI/PPy Nanocomposite for the Green Synthesis of Biologically Active 2,4,5-trisubstituted Imidazole Scaffolds

Overview

Journal Nanoscale Adv

Publisher Royal Society of Chemistry

Specialty Biotechnology

Date 2023 Apr 14

PMID 37056623

Authors

Sahil Kohli

Nisha

Garima Rathee

Sunita Hooda

Ramesh Chandra

Affiliations

Soon will be listed here.

Abstract

This work is focused on designing an innovative, efficient, and reusable heterogeneous ZnO/CuI/PPy nanocomposite the self-assembly approach where pyrrole is oxidized into polypyrrole (PPy) and pyrrole also behaves as a reductant in the presence of KI. This so-obtained material was characterized by XRD, FTIR, FESEM, EDX, TEM, XPS, and ICP. TEM clearly shows a spherical morphology with the particle size ranging between 18 and 42 nm. The fabricated nanomaterial was tested for one-pot catalytic synthesis of biologically active 2,4,5-trisubstituted imidazoles under solvent-free conditions. The present work includes the benefits of an easy work-up procedure, higher product yield, shorter reaction duration, and no additional additive requirement under green and sustainable conditions. Moreover, the catalyst exhibited reusability for six runs with no considerable reduction in the respective yields and reactivity (confirmed by XRD, SEM, and TEM of the recycled catalyst). The ICP study shows very low leaching of copper (2.08 ppm) and zinc (0.12 ppm) metals. The approach also presented better values of green metrics like the E-factor, process mass intensity, carbon efficiency and reaction mass efficiency.

Citing Articles

Green and efficient synthesis of 5-amino-1-pyrazole-5-carbonitriles utilizing novel modified LDH.

Momeni S, Ghorbani-Vaghei R Nanoscale Adv. 2024; .

PMID: 39430305 PMC: 11488685. DOI: 10.1039/d4na00577e.

FeO/PANI/CuI as a sustainable heterogeneous nanocatalyst for A coupling.

Nisha , Kohli S, Singh S, Sharma N, Chandra R Nanoscale Adv. 2024; 6(19):4842-4851.

PMID: 39323424 PMC: 11421548. DOI: 10.1039/d4na00448e.

References

Nair S, Sasidharan A, Rani V, Menon D, Nair S, Manzoor K . Role of size scale of ZnO nanoparticles and microparticles on toxicity toward bacteria and osteoblast cancer cells. J Mater Sci Mater Med. 2008; 20 Suppl 1:S235-41. DOI: 10.1007/s10856-008-3548-5. View

Hosseini Sarvari M, Sharghi H . Reactions on a solid surface. A simple, economical and efficient Friedel-Crafts acylation reaction over zinc oxide (ZnO) as a new catalyst. J Org Chem. 2004; 69(20):6953-6. DOI: 10.1021/jo0494477. View

Wang L, Woods K, Li Q, Barr K, McCroskey R, Hannick S . Potent, orally active heterocycle-based combretastatin A-4 analogues: synthesis, structure-activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation. J Med Chem. 2002; 45(8):1697-711. DOI: 10.1021/jm010523x. View

Gawande M, Goswami A, Felpin F, Asefa T, Huang X, Silva R . Cu and Cu-Based Nanoparticles: Synthesis and Applications in Catalysis. Chem Rev. 2016; 116(6):3722-811. DOI: 10.1021/acs.chemrev.5b00482. View

Ngouansavanh T, Zhu J . Alcohols in isonitrile-based multicomponent reaction: Passerini reaction of alcohols in the presence of o-iodoxybenzoic acid. Angew Chem Int Ed Engl. 2006; 45(21):3495-7. DOI: 10.1002/anie.200600588. View

Rathee G, Kohli S, Singh N, Awasthi A, Chandra R . Calcined Layered Double Hydroxides: Catalysts for Xanthene, 1,4-Dihydropyridine, and Polyhydroquinoline Derivative Synthesis. ACS Omega. 2020; 5(25):15673-15680. PMC: 7331214. DOI: 10.1021/acsomega.0c01901. View

Kappe C . Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog. Acc Chem Res. 2000; 33(12):879-88. DOI: 10.1021/ar000048h. View

Premanathan M, Karthikeyan K, Jeyasubramanian K, Manivannan G . Selective toxicity of ZnO nanoparticles toward Gram-positive bacteria and cancer cells by apoptosis through lipid peroxidation. Nanomedicine. 2010; 7(2):184-92. DOI: 10.1016/j.nano.2010.10.001. View

Kozhummal R, Yang Y, Guder F, Kucukbayrak U, Zacharias M . Antisolvent crystallization approach to construction of CuI superstructures with defined geometries. ACS Nano. 2013; 7(3):2820-8. DOI: 10.1021/nn4003902. View

10.

de Laszlo S, Hacker C, Li B, Kim D, MacCoss M, Mantlo N . Potent, orally absorbed glucagon receptor antagonists. Bioorg Med Chem Lett. 1999; 9(5):641-6. DOI: 10.1016/s0960-894x(99)00081-5. View

11.

Kohli S, Rathee G, Hooda S, Chandra R . AlO/CuI/PANI nanocomposite catalyzed green synthesis of biologically active 2-substituted benzimidazole derivatives. Dalton Trans. 2021; 50(22):7750-7758. DOI: 10.1039/d1dt00806d. View

12.

Yugandar S, Konda S, Parameshwarappa G, Ila H . One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles via [2 + 2 + 1] Cycloannulation of 1,3-Bishet(aryl)-monothio-1,3-diketones, α-Substituted Methylamines and Sodium Nitrite through α-Nitrosation of Enaminones. J Org Chem. 2016; 81(13):5606-22. DOI: 10.1021/acs.joc.6b00938. View

13.

Tanigawara Y, Aoyama N, Kita T, Shirakawa K, Komada F, Kasuga M . CYP2C19 genotype-related efficacy of omeprazole for the treatment of infection caused by Helicobacter pylori. Clin Pharmacol Ther. 1999; 66(5):528-34. DOI: 10.1016/S0009-9236(99)70017-2. View

14.

Indubala E, Dhanasekar M, Sudha V, Malar E, Divya P, Sherine J . l-Alanine capping of ZnO nanorods: increased carrier concentration in ZnO/CuI heterojunction diode. RSC Adv. 2022; 8(10):5350-5361. PMC: 9078177. DOI: 10.1039/c7ra12385j. View

15.

Elders N, Schmitz R, de Kanter F, Ruijter E, Groen M, Orru R . A resource-efficient and highly flexible procedure for a three-component synthesis of 2-imidazolines. J Org Chem. 2007; 72(16):6135-42. DOI: 10.1021/jo070840x. View

16.

Paravidino M, Bon R, Scheffelaar R, Vugts D, Znabet A, Schmitz R . Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality. Org Lett. 2006; 8(23):5369-72. DOI: 10.1021/ol062204b. View

17.

Rathee G, Kohli S, Panchal S, Singh N, Awasthi A, Singh S . Fabrication of a Gold-Supported NiAlTi-Layered Double Hydroxide Nanocatalyst for Organic Transformations. ACS Omega. 2020; 5(37):23967-23974. PMC: 7513357. DOI: 10.1021/acsomega.0c03250. View

18.

Ranu B, Dey R, Chatterjee T, Ahammed S . Copper nanoparticle-catalyzed carbon-carbon and carbon-heteroatom bond formation with a greener perspective. ChemSusChem. 2012; 5(1):22-44. DOI: 10.1002/cssc.201100348. View

19.

Kohli S, Rathee G, Hooda S, Chandra R . An efficient approach for the green synthesis of biologically active 2,3-dihydroquinazolin-4(1)-ones using a magnetic EDTA coated copper based nanocomposite. RSC Adv. 2023; 13(3):1923-1932. PMC: 9832363. DOI: 10.1039/d2ra07496f. View