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TiO2 nanoparticles supported on the Fe3O4@SiO2 nanocomposites: a novel magnetic nanocatalyst for the synthesis of 2-aminothiazoles

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Abstract

Nano TiO2 supported on the Fe3O4@SiO2 nanocomposites is introduced as a novel catalyst for the environmental synthesis of 2-aminothiazoles in PEG-200 as a green medium at room temperature. In this reaction, thiourea and N-bromosuccinimide were reacted with various ketones affording the desired 2-aminothiazole compounds. This green protocol has promising features for the reaction response such as simple procedure, high yields, and the ease of separation of pure product, short reaction time, and convenient manipulation. This catalyst was easily separated by an external magnet, and the recovered catalyst was reused several times without any significant loss of activity.

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References

  • Abdolmohammadi S (2013) Simple route to indeno[1,2-b]quinoline derivatives via a coupling reaction catalyzed by TiO2 nanoparticles. Chin Chem Let 24:318–320

    Article  Google Scholar 

  • Anastas PT (1996) Green Chemistry. In: Williamson TC (ed) ACS Symposium series 626. American Chemical Society, Washington

    Google Scholar 

  • Azizi N, Rahimi Z, Alipour M (2015) Deep eutectic solvent-assisted one-pot synthesis of 2-aminothiazole and 2-aminoxazole derivatives. C R Chim 18:626–629

    Article  Google Scholar 

  • Banothu J, Vaarla K, Bavantula R, Crooks PA (2014) Sodium fluoride as an efficient catalyst for the synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles at ambient temperature. Chin Chem Lett 25:172–175

    Article  Google Scholar 

  • Chen W, Zhong LX, Peng XW, Wang K, Chen ZF, Sun RC (2014) Xylan-type hemicellulose supported palladium nanoparticles: a highly efficient and reusable catalyst for the carbon–carbon coupling reactions. Catal Sci Technol 4:1426–1435

    Article  Google Scholar 

  • Clemence F, Martret OL, Delevallee F, Benzoni J, Jouanen A, Jouquey S, Mouren M, Deraedt R (1988) 4-Hydroxy-3-quinolinecarboxamides with antiarthritic and analgesic activities. J Med Chem 31:1453–1462

    Article  Google Scholar 

  • Das B, Reddy SV, Ramu R (2006) A rapid and high-yielding synthesis of thiazoles and aminothiazoles using ammonium-12-molybdophosphate. J Mol Catal A: Chem 252:235–237

    Article  Google Scholar 

  • Dhital RN, Kamonsatikul C, Somsook E, Bobuatong K, Ehara M, Karanjit S, Sakurai H (2012) Low-temperature carbon–chlorine bond activation by bimetallic gold/palladium alloy nanoclusters: An application to Ullmann coupling. J Am Chem Soc 134:20250–20253

    Article  Google Scholar 

  • Diallo AK, Ornelas C, Salmon L, Aranzaes JR, Astruc D (2007) “Homeopathic” catalytic activity and atom-leaching mechanism in Miyaura-Suzuki reactions under ambient conditions with precise dendrimer-stabilized Pd nanoparticles. Angew Chem Int Ed 46:8644–8648

    Article  Google Scholar 

  • Fan Y, Ma C, Li W, Yin Y (2012) Synthesis and properties of Fe3O4/SiO2/TiO2 nanocomposites by hydrothermal synthetic method. Semicond Process 15:582–585

    Article  Google Scholar 

  • Ghodse SM, Telvekar VN (2015) Synthesis of 2-aminothiazole derivatives from easily available thiourea and alkyl/aryl ketones using aqueous NaICl2. Tetrahedron Lett 56:472–474

    Article  Google Scholar 

  • Haviv F, Ratajczyk JD, DeNet RW, Kerdesky FA, Walters RL, Schmidt SP, Holms JH, Young PR, Carter GW (1988) 3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives: inhibitors of immune complex induced inflammation. J Med Chem 31:1719–1728

    Article  Google Scholar 

  • Hosseini-Sarvari M (2007) Titania (TiO2)-catalyzed expedient, solventless and mild synthesis of bis(indolyl)methanes. Acta Chim Slov 54:354–359

    Google Scholar 

  • Huang X, Wang G, Yang M, Guo W, Gao H (2011) Synthesis of polyaniline-modified Fe3O4/SiO2/TiO2 composite microspheres and their photocatalytic application. Mater Let 65:2887–2890

    Article  Google Scholar 

  • Iwasaki M, Shinjoh H (2011) Hydrothermal stability enhancement by sequential ion-exchange of rare earth metals on Fe/BEA zeolites used as NO reduction catalysts. Chem Commun 47:3966–3968

    Article  Google Scholar 

  • Jaen JC, Wise LD, Caprathe BW, Tecle H, Bergmeier S, Humblet CC, Heffner TG, Meltzner LT, Pugsley TA (1990) 4-(1,2,5,6-Tetrahydro-1-alkyl-3-pyridinyl)-2-thiazolamines: a novel class of compounds with central dopamine agonist properties. J Med Chem 33:311–317

    Article  Google Scholar 

  • Karade H, Sathe M, Kaushik MP (2007) An efficient method for the synthesis of 2-aminothiazoles using silica chloride as a heterogeneous catalyst. Catal Commun 8:741–746

    Article  Google Scholar 

  • Kariuki NN, Wang X, Mawdsley JR, Ferrandon MS, Niyogi SG, Vaughey JT, Myers DJ (2010) Colloidal synthesis and characterization of carbon-supported Pd–Cu nanoparticle oxygen reduction electrocatalysts. Chem Mater 22:4144–4152

    Article  Google Scholar 

  • Kidwai M, Bansal V, Mirsha NK, Kumar A, Mozumdar S (2007) Copper-nanoparticle-catalyzed A3 coupling via CH activation. Synlett 10:1581–1584

    Article  Google Scholar 

  • King LC, Hlavacek RJ (1950) The reaction of ketones with iodine and thiourea. J Am Chem Soc 72:3722–3725

    Article  Google Scholar 

  • Liu X, Wang A, Yang X, Zhang T, Mou CY, Su DS, Li J (2009) Synthesis of Thermally stable and highly active bimetallic Au–Ag nanoparticles on inert supports. Chem Mater 21:410–418

    Article  Google Scholar 

  • Narender M, Reddy MS, Sridhar R, Nageswar K, Nageswar K, Rao KR (2005) Aqueous phase synthesis of thiazoles and aminothiazoles in the presence of β-cyclodextrin. Tetrahydron Lett 46:5953–5955

    Article  Google Scholar 

  • Noei J, Khosropour AR (2009) Ultrasound-promoted a green protocol for the synthesis of 2,4-diarylthiazoles under ambient temperature in [bmim]BF4. Ultrason Sonochem 16:711–717

    Article  Google Scholar 

  • Park YS, Kim K (1999) 4-Chloro-5H-1,2,3-dithiazol-5-one: a good α-thiocyanating agent for α, β-unsaturated β-amino esters. Tetrahedron Lett 40:6439–6442

    Article  Google Scholar 

  • Potewar TM, Ingale SA, Srinivasan KV (2007) Efficient synthesis of 2,4-disubstituted thiazoles using ionic liquid under ambient conditions: a practical approach towards the synthesis of Fanetizole. Tetrahedron 63:11066–11069

    Article  Google Scholar 

  • Ropero-Vega JL, Aldana-Péreza A, Gómez R, Niño-Gómez ME (2010) Sulfated titania [TiO2/SO4 2−]: A very active solid acid catalyst for the esterification of free fatty acids with ethanol. Appl Catal 379:24–29

    Article  Google Scholar 

  • Rostamizadeh S, Aryan R, Ghaieni HR, Amani AM (2008) Aqueous NaHSO4 catalyzed regioselective and versatile synthesis of 2-thiazolamines. Monatsh Chem 139:1241–1245

    Article  Google Scholar 

  • Safari J, Zarnegar Z (2013) A magnetic nanoparticle-supported sulfuric acid as a highly efficient and reusable catalyst for rapid synthesis of amidoalkyl naphthols. J Mol Catal A 379:269–276

    Article  Google Scholar 

  • Safari J, Zarnegar Z, Heydarian M (2012) Magnetic Fe3O4 nanoparticles as novel and efficient catalyst for the green synthesis of 2-amino-4H-chromene in aqueous media. Bull Chem Soc Jpn 85:1332–1338

    Article  Google Scholar 

  • Sajadi SM, Naderi M, Babadoust S (2011) Nano TiO2 as an efficient and reusable heterogeneous catalyst for the synthesis of 5-substituted 1H-tetrazoles. Nat Sci Res 1:10–17

    Google Scholar 

  • Shirini F, Alipour Khoshdel M, Abedini M, Atghia SD (2011a) Nanocrystalline TiO2 as an efficient and reusable catalyst for the chemoselective trimethylsilylation of primary and secondary alcohols and phenols. Chin Chem Lett 22:1211–1214

    Google Scholar 

  • Shirini F, Atghia SV, Alipour Khoshdel M (2011b) Nanocrystalline TiO2 as an efficient and reusable catalyst for the one-pot synthesis of polyhydroquinolien derivatives via Hantzsch reaction. Iran J Catal 1:93–97

    Google Scholar 

  • Sultane PR, Mete TB, Bhat BRG (2014) Chemoselective N-deacetylation under mild conditions. Org Biomol Chem 12:261–264

    Article  Google Scholar 

  • Tsuji K, Ishikawa H (1994) Synthesis and anti-pseudomonal activity of new 2-isocephems with a dihydroxypyridone moiety at C-7. Bioorg Med Chem Lett 4:1601–1606

    Article  Google Scholar 

  • Yadav JS, Subba Reddy BV, Gopala Rao Y, Narsaiah AV (2008) First example of the coupling of α-diazoketones with thiourea: a novel route for the synthesis of 2-aminothiazoles. Tetrahedron Lett 49:2381–2383

    Article  Google Scholar 

  • Zhu D, Chen J, Xiao H, Liu M, Ding J, Wu H (2009) Efficient and expeditious synthesis of di- and trisubstituted thiazoles in PEG under catalyst-free conditions. Synth Commun 39:2895–2906

    Article  Google Scholar 

  • Zhu YP, Yuan JJ, Zhao Q, Lian M, Gao QH, Liu MC, Yang Y, Wu AX (2012) I2/CuO-catalyzed tandem cyclization strategy for one-pot synthesis of substituted 2-aminothiozole from easily available aromatic ketones/α, β-unsaturated ketones and thiourea. Tetrahedron 68:173–178

    Article  Google Scholar 

  • Zorn K, Giorgio S, Halwax E, Henry CR, Grönbeck H, Rupprechter G (2011) Synthesis of thermally stable and highly active bimetallic Au–Ag nanoparticles on inert supports. J Phys Chem C 115:1103–1111

    Article  Google Scholar 

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Acknowledgments

We gratefully acknowledge the financial support from the Research Council of the University of Kashan for supporting this work by Grant No. (256722/III).

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Correspondence to Zohre Zarnegar.

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Safari, J., Abedi-Jazini, Z., Zarnegar, Z. et al. TiO2 nanoparticles supported on the Fe3O4@SiO2 nanocomposites: a novel magnetic nanocatalyst for the synthesis of 2-aminothiazoles. J Nanopart Res 17, 495 (2015). https://doi.org/10.1007/s11051-015-3298-5

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