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Current Organocatalysis

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ISSN (Print): 2213-3372
ISSN (Online): 2213-3380

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Research Article

Microwave-assisted One-pot Synthesis of 2-Substituted Quinolines by Using Palladium Nanoparticles as a Catalyst developed from Green Alga Botryococcus braunii

Author(s): Anju Arya, Akhil Mahajan and Tejpal Singh Chundawat*

Volume 7, Issue 2, 2020

Page: [82 - 88] Pages: 7

DOI: 10.2174/2213337206666190625112833

Abstract

Background: Quinoline is a type of N-based organic heterocyclic biologically active compound. Quinolines have grasped the interest of scientists because of their wide scope of applications. Several methods have been developed for the synthesis of quinoline and its derivatives. In this study, a new, efficient, simple, one-pot synthesis of the substituted quinolines was developed by using palladium nanoparticles as a catalyst.

Methods: Catalyst synthesized by algal extract of green alga Botryococcus braunii and palladium acetate solution, and characterized by different instrumental techniques like FTIR, SEM, and XRD. The synthesized palladium nanoparticles explored for the catalytic activity in the synthesis of quinoline derivatives by the use of 2-aminobenzyl alcohol in toluene with acetyl derivatives followed by the addition of potassium hydroxide. The formation of the product was confirmed by 1HNMR, 13C NMR, and electron ionization mass spectra.

Results: The formation of palladium nanoparticles characterized by visual observation means the color change from light pale yellow to dark brown indicates the reduction of palladium ions into palladium nanoparticles. Synthesized palladium nanoparticles characterized by FTIR spectrum of the algal extract of green algae B. braunii for the presence of proteins, lipids, carbohydrates, carotenoids, vitamins and other secondary metabolites in algal extract, which function as active components for bioreduction. The morphology of the catalyst was confirmed by SEM and X-ray diffraction measurements for shape, crystalline nature and size. The synthesized palladium nanoparticles explored for the catalytic activity in the synthesis of quinoline derivatives by use of 2-aminobenzyl alcohol in toluene and added acetyl derivatives followed by the addition of potassium hydroxide. In order to establish the optimum heating method, a comparative study between conventional and microwave heating method was carried out in the presence of palladium nanoparticles as a catalyst.

Conclusion: This protocol provides a convenient and practical procedure for the preparation of quinoline derivatives from 2-aminobenzyl alcohol, acetyl derivatives, potassium hydroxide and palladium nanoparticles as a catalyst. This protocol will be helpful in synthesizing other quinoline derivatives and several organic heterocycles which are used in different fields such as biological, industrial, pharmaceutical, chemical, medical, etc.

Keywords: Green alga, microwave heating, palladium nanoparticles, quinolone, Botryococcus braunii, one-pot synthesis.

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[1]
Runge, F.F. On some products of coal distillation. Ann. Phy. Chem., 1834, 31, 65-78.
[http://dx.doi.org/10.1002/andp.18341070502]
[2]
Kouznetsov, V.V.; Menndez, L.Y.; Gomez, C.M. Recent progress in the synthesis of quinolones. Curr. Org. Chem., 2005, 9, 141-161.
[3]
Cunico, W.; Cechinel, C.A.; Bonacorso, H.G.; Martins, M.A.; Zanatta, N.; de Souza, M.V.; Freitas, I.O.; Soares, R.P.; Krettli, A.U. Antimalarial activity of 4-(5-trifluoromethyl-1H-pyrazol-1-yl)-chloroquine analogues. Bioorg. Med. Chem. Lett., 2006, 16(3), 649-653.
[http://dx.doi.org/10.1016/j.bmcl.2005.10.033] [PMID: 16257205]
[4]
Divo, A.A.; Sartorelli, A.C.; Patton, C.L.; Bia, F.J. Activity of fluoroquinolone antibiotics against Plasmodium falciparum in vitro. Antimicrob. Agents Chemother., 1988, 32(8), 1182-1186.
[http://dx.doi.org/10.1128/AAC.32.8.1182] [PMID: 2847647]
[5]
Görlitzer, K.; Gabriel, B.; Jomaa, H.; Wiesner, J. Thieno[3,2-c]chinolin-4-yl-amine--Synthese und Prŭfung auf Wirksamkeit gegen Malaria. Pharmazie, 2006, 61(4), 278-284.
[PMID: 16649537]
[6]
Khan, M.O.; Levi, M.S.; Tekwani, B.L.; Wilson, N.H.; Borne, R.F. Synthesis of isoquinuclidine analogs of chloroquine: antimalarial and antileishmanial activity. Bioorg. Med. Chem., 2007, 15(11), 3919-3925.
[http://dx.doi.org/10.1016/j.bmc.2006.11.024] [PMID: 17400457]
[7]
Kayirere, M.; Mahmoud, A.; Chevalier, J.; Soyfer, J.; Cremieux, A.; Barbe, J.; Eur, J. Synthesis and antibacterial activity of new 4-alkoxy, 4-aminoalkyl and 4-alkylthioquinoline derivatives. Med. Chem. (N.Y.), 1998, 33, 55-63.
[http://dx.doi.org/10.1016/S0223-5234(99)80076-2]
[8]
Kidwai, M.; Bhushan, K.R.; Sapra, P.; Saxena, R.K.; Gupta, R. Alumina-supported synthesis of antibacterial quinolines using microwaves. Bioorg. Med. Chem., 2000, 8(1), 69-72.
[http://dx.doi.org/10.1016/S0968-0896(99)00256-4] [PMID: 10968266]
[9]
Ryu, C.K.; Sun, Y.J.; Shim, J.Y.; You, H.J.; Choi, K.U.; Lee, H. Synthesis and antifungal activity of 6,7-bis-[S-(aryl)thio]-5,8-quinolinediones. Arch. Pharm. Res., 2002, 25(6), 795-800.
[http://dx.doi.org/10.1007/BF02976994] [PMID: 12510828]
[10]
Musiol, R.; Jamilek, J.; Buchta, V.; Silva, L.; Niedbala, H.; Podeszwa, B.; Palka, A.; Maniecka, K.M.; Oleksyn, B.; Polanski, J.A.; Palka, K.M. Maniecka; B, Oleksyn.; J, Polanski. Antifungal properties of new series of quinoline derivatives. Bioorg. Med. Chem., 2006, 14, 3592-3598.
[http://dx.doi.org/10.1016/j.bmc.2006.01.016] [PMID: 16458522]
[11]
Desai, U.; Mitragotri, S.; Thopate, T.; Pore, D.; Wadgaonkarb, P. A highly efficient synthesis of trisubstituted quinolines using sodium hydrogensulfate on silica gel as a reusable catalyst. ARKIVOC, 2006, 15, 198-204.
[12]
Elderfield, R.C.; Le Von, E.F.J. Synthesis of potential anticancer agents.III. Nitrogen mustards derived from 8- aminoquinolines. Org. Chem., 1960, 25, 1576-1583.
[http://dx.doi.org/10.1021/jo01079a027]
[13]
Denny, W.A.; Wilson, W.R.; Ware, D.C.; Atwell, G.J.; Milbank, J.B.; Stevenson, R.J. Stevenson, Anticancer 2,3-dihydro-1Hpyrrolo[ 3,2-f]quinoline complexes of cobalt and chromium US Patent 7064117B2.
[14]
Ebenso, E.E.; Kabanda, M.M.; Arland, T.; Saracoglu, M.; Kandemirli, F.; Murulana, L.C.; Singh, A.K.; Shukla, S.K.; Hammouti, B.; Khaled, K. Quantum chemical investigations on quinoline derivatives as effective corrosion inhibitors for mild steel in acidic medium. Int. J. Electrochem. Sci., 2012, 7, 5643-5676.
[15]
Gogoi, S.; Shekarrao, K.; Duarah, A.; Bora, T.C.; Gogoi, S.; Boruah, R.C. A microwave promoted solvent-free approach to steroidal quinolines and their in vitro evaluation for antimicrobial activities. Steroids, 2012, 77(13), 1438-1445.
[http://dx.doi.org/10.1016/j.steroids.2012.08.008] [PMID: 22960652]
[16]
Mahajan, A.; Chundawat, T.S. Review on the role of metal catalyst in the synthesi of pharmacologically important quinoline substrate. Mini Rev. Org. Chem., 2019, 7, 631-652.
[17]
Aditya, T.; Pal, A.; Pal, T. Nitroarene reduction: a trusted model reaction to test nanoparticle catalysts. Chem. Commun. (Camb.), 2015, 51(46), 9410-9431.
[http://dx.doi.org/10.1039/C5CC01131K] [PMID: 25872865]
[18]
Parmanik, S.; Das, M.R.; Das, D.; Das, P. Sustainable redox chemistry route to multifaceted Fe-Pd heteronanostructure: Delving into the synergistic influence in catalysis. ChemistrySelect, 2017, 2, 4577-4585.
[http://dx.doi.org/10.1002/slct.201700714]
[19]
Davis, S.E.; Ide, M.S.; Davis, R.J. Davis. Selective oxidation of alcohols and aldehydes over supported metal nanoparticles. Green Chem., 2013, 15, 17-45.
[http://dx.doi.org/10.1039/C2GC36441G]
[20]
Sheldon, R.A. Recent advances in green catalytic oxidation of alcohols in aqueous media. Catal. Today, 2015, 247, 4-13.
[http://dx.doi.org/10.1016/j.cattod.2014.08.024]
[21]
Lennox, A.J.J.; Lloyd-Jones, G.C. Selection of boron reagents for Suzuki-Miyaura coupling. Chem. Soc. Rev., 2014, 43(1), 412-443.
[http://dx.doi.org/10.1039/C3CS60197H] [PMID: 24091429]
[22]
Arya, A.; Gupta, K.; Chundawat, T.S.; Vaya, D. Biogeneic synthesis of copper and silver nanoparticles using green alaga Botryococcus brauni and its antimicrobial activity. Bioinorg. Chem. Appl., 2018, 2018, 7879403
[http://dx.doi.org/10.1155/2018/7879403] [PMID: 30420873]
[23]
Hazarika, M.; Borah, D.; Bora, P.; Silva, A.R.; Das, P. Biogenic synthesis of palladium nanoparticles and their applications as catalyst and antimicrobial agent. PLoS One, 2017, 12(9) e0184936
[http://dx.doi.org/10.1371/journal.pone.0184936] [PMID: 28957342]
[24]
Aboelfetoh, E.F. EI-Shenody; Ghobara, M. M. (2017) Eco-friendly synthesis of silver nanoparticles using green alga (Caulerpa serrulata): reaction optimization, catalytic and antibacterial activities. Environ. Monit. Assess., 2017, 189, 349.
[http://dx.doi.org/10.1007/s10661-017-6033-0] [PMID: 28646435]
[25]
Sharma, B.; Purkayastha, D.D.; Hazra, S.; Gogoi, L.; Bhattacharjee, C.R.; Ghosh, N.N.; Rout, J. Biosynthesis of gold nanoparticles using fresh water green alga Prasiola crispa. Mater. Lett., 2013, 116, 94-97.
[http://dx.doi.org/10.1016/j.matlet.2013.10.107]
[26]
Shende, S.; Gade, A.; Rai, M. Large scale synthesis and antibacterial activity of fungal derived silver nanoparticles. Environ. Chem. Lett., 2016, 15, 427-434.
[http://dx.doi.org/10.1007/s10311-016-0599-6]
[27]
Ramakrishana, M.; Babu, D.R.; Gengan, R.M.; Chandra, S.; Rao, G.N. Green synthesis of gold nanoparticles using marine algae and evaluation of their catalytic activity. J. Nanostruct. Chem., 2015, 6, 1-13.
[http://dx.doi.org/10.1007/s40097-015-0173-y]
[28]
Oza, G.; Pandey, S.; Mewada, A.; Kalita, G.; Sharon, M. Facile biosynthesis of gold nanoparticles Exploiting optimum pH and temperature of fresh water algae Chlorella pyrenoidusa. Adv. Appl. Sci. Res., 2012, 3, 1405-1412.
[29]
Rajesh Kumar, S.; Kanna, A.C.; Annadurai, G. Green synthesis of silver nanoparticles using marine brown alga Turbinaria conoids and its antibacterial activity. Int. J. Pharma Bio Sci., 2012, 2012(3), 502-510.
[30]
Azizi, S.; Mahdavi Shahri, M.; Rahman, H.S.; Rahim, R.A.; Rasedee, A.; Mohamad, R. Green synthesis palladium nanoparticles mediated by white tea (Camellia sinensis) extract with antioxidant, antibacterial, and antiproliferative activities toward the human leukemia (MOLT-4) cell line. Int. J. Nanomedicine, 2017, 12, 8841-8853.
[http://dx.doi.org/10.2147/IJN.S149371] [PMID: 29276385]

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