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Synthesis of new 2-amino-4H-pyran-3,5-dicarboxylate derivatives using nanocrystalline MIIZr4(PO4)6 ceramics as reusable and robust catalysts under microwave irradiation

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Abstract

In the present paper, we report the successful synthesis of nanocrystalline MIIZr4(PO4)6 ceramics (M: Mn, Ni, Fe, Co). These nano-structures were characterized by X-ray diffraction, scanning electron microscopy, and vibrating sample magnetometer (VSM). Size of nano-structures was in the range of 20–150 nm. Nano-MIIZr4(PO4)6 as an efficient and green catalyst has been used for the preparation of 2-amino-4H-pyran-3,5-dicarboxylate derivatives by the three-component condensation reaction of ethyl cyanoacetate, ethyl acetoacetate, and various aromatic aldehydes under microwave irradiation. Extraordinarily, the best results were obtained using MnZr4(PO4)6 nanocrystallines as an efficient catalyst. This method provides several advantages including easy work-up, excellent yields, short reaction times, using of microwave as green method, recoverability of the catalyst, and little catalyst loading.

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References

  • Abahmane L, Köhler JM, Groß GA (2011) Gold-nanoparticle-catalyzed synthesis of propargylamines: the traditional A3-multicomponent reaction performed as a two-step flow process. Chem Eur J 17:3005–3010

    Article  Google Scholar 

  • Alonso F, Moglie Y, Radivoy G, Yus M (2011) Multicomponent click synthesis of 1,2,3-Triazoles from epoxides in water catalyzed by copper nanoparticles on activated carbon. J Org Chem 76:8394–8405

    Article  Google Scholar 

  • Banerjee S, Horn A, Khatri H, Sereda G (2011) A green one-pot multicomponent synthesis of 4H-pyrans and polysubstituted aniline derivatives of biological, pharmacological, and optical applications using silica nanoparticles as reusable catalyst. Tetrahedron Lett 52:1878–1881

    Article  Google Scholar 

  • Bhattacharyya P, Pradhan K, Paul S, Das AR (2012) Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media. Tetrahedron Lett 53:4687–4691

    Article  Google Scholar 

  • Bhunia A, Kaicharla T, Porwal D, Gonnade RG, Biju AT (2014) Multicomponent reactions involving phosphines, arynes and aldehydes. Chem Commun 50:11389–11392

    Article  Google Scholar 

  • Chanda K, Rej S, Huang MH (2013) Facet-dependent catalytic activity of Cu2O nanocrystals in the one-pot synthesis of 1,2,3-Triazoles by multicomponent click reactions. Chem Eur J 19:16036–16043

    Article  Google Scholar 

  • Chen WB, Wu ZJ, Pei QL, Cun LF, Zhang XM, Yuan WC (2010) Highly enantioselective construction of spiro[4H-pyran-3,3′-oxindoles] through a Domino Knoevenagel/Michael/Cyclization sequence catalyzed by cupreine. Org Lett 12:3132–3135

    Article  Google Scholar 

  • Este´vez V, Villacampa M, Mene´ndez JC (2010) Multicomponent reactions for the synthesis of pyrroles. Chem Soc Rev 39:4402–4421

    Article  Google Scholar 

  • Gawande MB, Velhinho A, Nogueira ID, Ghumman CAA, Teodoro OMND, Branco PS (2012) A facile synthesis of cysteine–ferrite magnetic nanoparticles for application in multicomponent reactions-a sustainable protocol. RSC Adv 2:6144–6149

    Article  Google Scholar 

  • Gorodylova N, Kosinova V, Dohnalova Z, Belina P, Sulcova P (2013) New purple-blue ceramic pigments based on CoZr4(PO4)6. Dyes Pigments 98:393–404

    Article  Google Scholar 

  • Gubin SP (2009) Magnetic nanoparticles. WILEY-VCH Verlag GmbH & Co.KGaA, Weinheim

    Book  Google Scholar 

  • Kamdar NR, Haveliwala DD, Mistry PT, Patel SK (2010) Design, synthesis and in vitro evaluation of antitubercular and antimicrobial activity of some novel pyranopyrimidines. Eur J Med Chem 45:5056–5063

    Article  Google Scholar 

  • Kidwai M, Jahan A, Kumar Mishra N (2012) Gold(III) chloride (HAuCl4·3H2O) in PEG: a new and efficient catalytic system for the synthesis of functionalized spirochromenes. Appl Catal A Gen 425–426:35–43

    Article  Google Scholar 

  • Koukabi N, Kolvari E, Khazaei A, Zolfigol MA, Shirmardi-Shaghasemi B, Khavasi HR (2011) Hantzsch reaction on free nano-Fe2O3 catalyst: excellent reactivity combined with facile catalyst recovery and recyclability. Chem Commun 47:9230–9232

    Article  Google Scholar 

  • Kumar D, Reddy VB, Sharad S, Dube U, Kapur S (2009) A facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes. Eur J Med Chem 44:3805–3809

    Article  Google Scholar 

  • Liu DM (1994) Thermal diffusivity of porous (Ca 1-xMgx)Zr4(P04)6 ceramic. Mater Chem Phys 36:350–353

    Article  Google Scholar 

  • Naeimi H, Rashid Z, Zarnani AH, Ghahremanzadeh R (2014) Nanocrystalline magnesium oxide: an efficient promoter and heterogeneous nano catalyst for the one-pot synthesis of pyrazolotriazoles in green medium. J Nanoparticle Res 16:2416

    Article  Google Scholar 

  • Pansuriya AM, Savant MM, Bhuva CV, Singh J, Naliapara YT (2009) Use of cyclic aliphatic ketones for spiro 2-amino-3-cyano pyrano[3,2-c]chromene formation. ARKIVOC xii:254–260

    Google Scholar 

  • Patil SA, Wang J, Li XS, Chen JJ, Jones TS, Hosni-Ahmed A, Patil R, Seibel WL, Li W, Miller DD (2012) New substituted 4H-chromenes as anticancer agents. Bioorg Med Chem Lett 22:4458–4461

    Article  Google Scholar 

  • Safaei-Ghomi J, Kalhor S (2015) A convenient synthesis of 2-aminocyclohex-1-ene-1-carboxylic esters by FeCl3/SiO2 nanoparticles as robust and efficient catalyst. Chin Chem Lett 26:735–738

    Article  Google Scholar 

  • Safaei-Ghomi J, Shahbazi-Alavi H, Heidari-Baghbahadorani E (2014) SnO nanoparticles as an efficient catalyst for the one-pot synthesis of chromeno[2,3-b]pyridines and 2-amino-3,5-dicyano-6-sulfanyl pyridines. RSC Adv 4:50668–50677

    Article  Google Scholar 

  • Saundane AR, Vijaykumar K, Vaijinath AV (2013) Synthesis of novel 2-amino-4-(5′-substituted 2′-phenyl-1H-indol-3′-yl)-6-aryl-4H-pyran-3-carbonitrile derivatives as antimicrobial and antioxidant agents. Bioorg Med Chem Lett 23:1978–1984

    Article  Google Scholar 

  • Tanabe K (1970) Solid acids and bases. Academic Press, New York

    Book  Google Scholar 

  • Venkatesham A, Rao RS, Nagaiah K, Yadav JS, RoopaJones G, Basha SJ, Sridhar B, Addlagatta A (2012) Synthesis of new chromeno-annulated cis-fused pyrano[3,4-c]pyran derivatives via domino Knoevenagel-hetero-Diels-Alder reactions and their biological evaluation towards antiproliferative activity. Med Chem Commun 3:652–658

    Article  Google Scholar 

  • Wang Y, Xin X, Liang Y, Lin Y, Duan H, Dong D (2009) N, N, N´, N´-tetramethylchloroformamidinium chloride-mediated cyclizations of β-oxo amides: facile and divergent one-pot synthesis of substituted 2H-pyrans, 4H-pyrans and pyridin-2(1H)-ones. Adv Synth Catal 351:2217–2223

    Article  Google Scholar 

  • Zhu Y, Xie M, Dong S, Zhao X, Lin L, Liu X, Feng X (2011) Asymmetric cycloaddition of b, g-unsaturated a-ketoesters with electron-rich alkenes catalyzed by a chiral Er(OTf)3/N, N´-dioxide complex: highly enantioselective synthesis of 3,4-dihydro-2H-pyrans. Chem Eur J 17:8202–8208

    Article  Google Scholar 

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Acknowledgments

The authors acknowledge a reviewer who provided helpful insights. The authors are grateful to University of Kashan for supporting this work by Grant No. 159148/22.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, 87317, Islamic Republic of Iran

    Javad Safaei-Ghomi & Hossein Shahbazi-Alavi

  2. Nano-Research Center, Imam Hossein University, PO Box 16575-347, Tehran, Iran

    Abdollah Javidan

  3. School of Chemistry, College of Science, University of Tehran, Tehran, 14155-6455, Iran

    Abolfazl Ziarati

Authors
  1. Javad Safaei-Ghomi
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  2. Abdollah Javidan
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  3. Abolfazl Ziarati
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  4. Hossein Shahbazi-Alavi
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Correspondence to Javad Safaei-Ghomi.

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Safaei-Ghomi, J., Javidan, A., Ziarati, A. et al. Synthesis of new 2-amino-4H-pyran-3,5-dicarboxylate derivatives using nanocrystalline MIIZr4(PO4)6 ceramics as reusable and robust catalysts under microwave irradiation. J Nanopart Res 17, 338 (2015). https://doi.org/10.1007/s11051-015-3142-y

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  • DOI: https://doi.org/10.1007/s11051-015-3142-y

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