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γ-Alumina Catalyzed Green Synthesis of Pyran’s Annulated Heterocyclic Systems via Three-Component Reaction

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Abstract

γ-Alumina was found as a new efficient heterogeneous catalyst for the synthesis of pyran’s annulated heterocyclic systems. Three-component reaction of various aromatic aldehydes, malononitrile and cyclic CH-acids in the presence of γ-alumina in H2O as a green solvent at 50 °C gave pyran derivatives in high yields. γ-Alumina has some advantages such as cheap, available and recyclable.

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References

  • Alizadeh A, Khodaei MM, Beygzadeh M, Kordestani D, Feyzi M (2012) Biguanide-functionalized Fe3O4/SiO2 magnetic nanoparticles: an efficient heterogeneous organosuperbase catalyst for various organic transformations in aqueous media. Bull Korean Chem Soc 33(8):2546–2552

    Article  Google Scholar 

  • Aswin K, Sheik Mansoor S, Logaiya K, Sudhan SPN, Saleem Malik V, Ramadoss H (2014) Reusable silica-bonded S-sulfonic acid catalyst for three-component synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes and 2-amino-4H-pyrans in aqueous ethanol. Res Chem Intermed 40(8):2583–2598

    Article  Google Scholar 

  • Baghbanian SM, Rezaei N, Tashakkorian H (2013) Nanozeolite clinoptilolite as a highly efficient heterogeneous catalyst for the synthesis of various 2-amino-4H-chromene derivatives in aqueous media. Green Chem 15(12):3446–3458

    Article  Google Scholar 

  • Bonsignore L, Loy G, Secci D, Calignano A (1993) Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives. Eur J Med Chem 28(6):517–520

    Article  Google Scholar 

  • Coates WJ (1990) Preparation of pyrimidopyrimidine derivatives useful as bronchodilators, vasodilators, antiallergic. European Patent 351058

  • Davoll J, Clarke J, Elslager EF (1972) Antimalarial substances. 26. Folate antagonists. 4. Antimalarial and antimetabolite effects of 2,4-diamino-6-[(benzyl)amino]pyrido[2,3-d]pyrimidines. J Med Chem 15(8):837–839

    Article  Google Scholar 

  • Edjlali L (2008) The regiospecific synthesis of some new 3,5-disubstituted isoxazoles. J Chin Chem Soc 55(6):1322–1325

    Article  Google Scholar 

  • Fenn D (ed) (1994) The pyrimidines. Wiley, New York

    Google Scholar 

  • Ghorab MM, Hassan AY (1998) Synthesis and antibacterial properties of new dithienyl containing pyran, pyrano[2,3-b] pyridine, pyrano[2,3-d]pyrimidine and pyridine derivatives. Phosphorus Sulfur Silicon Relat Elem 141(1):251–261

    Article  Google Scholar 

  • Grieco PA (1998) Organic synthesis in water. Blackie, New York

    Book  Google Scholar 

  • Kidwai M, Jain A, Bhardwaj S (2012) Magnetic nanoparticles catalyzed synthesis of diverse N-Heterocycles. Mol Divers 16(1):121–128

    Article  Google Scholar 

  • Kitamura N, Onishi A (1984). European patent 163599

  • Konkoy CS, Fick DB, Cai SX, Lan NC, Keana JFW (2000) Substituted 5-oxo-5, 6,7,8-tetrahydro-4H-1-benzopyrans and benzothiopyrans and their use as potentiators of AMPA. PCT Int Appl, WO Patent 0075123

    Google Scholar 

  • Levitt G (1982) Herbicidal sulfonamides, US Patent 4339267

  • Mandelli D, van Vliet MCA, Sheldon RA, Schuchardt U (2001) Aluminium catalyzed alkene epoxidation with hydrogen peroxide. Appl Catal A 219(1):209–213

    Article  Google Scholar 

  • Min BK, Friend CM (2007) Heterogeneous gold-based catalysis for green chemistry: low-temperature CO oxidation and propene oxidation. Chemical Review 107(6):2709–2724

    Article  Google Scholar 

  • Mirzaei YR, Edjlali L (2010) Synthesis and characterization of 2-alkyl-5-{4-[(3-nitrophenyl-5-isoxazolyl)methoxy]phenyl}-2H-tetrazoles. J Iran Chem Soc 7(3):685–694

    Article  Google Scholar 

  • Nagendrappa G (2002) Organic synthesis under solvent-free condition: an environmentally benign procedure-I. Resonance 7(10):59–68

    Article  Google Scholar 

  • Oberlander K (1984) Applied industrial catalysis In: Leach BE (ed.), Academic Press, New York, p.63

  • Sarrafi Y, Mehrasbi E, Vahid A, Tajbakhsh M (2012) Well-ordered mesoporous silica nanoparticles as a recoverable catalyst for one-pot multicomponent synthesis of 4H-chromene derivatives. Chin J Catal V33(9):1486–1494

    Article  Google Scholar 

  • Sepulveda J, Teixeir S, Schuchardt U (2007) Alumina-catalyzed epoxidation of unsaturated fatty esters with hydrogen peroxide. Appl Catal A 318(1–2):213–217

    Article  Google Scholar 

  • Varma RS, Namboodiri VV (2001) Solvent-free preparation of ionic liquids using a household microwave oven. Pure Appl Chem 73(8):1309–1313

    Article  Google Scholar 

  • Wefers K (1990) Alumina chemicals: science and technology hand-book. In: Hart LD (ed.), The American Ceramic Society, Westerville, Ohio, p.13

  • Witte EC, Neubert P, Roesch A (1986) 7-(piperazinyl propoxy)-2H-1-benzopyran-2-ones. Ger Offen DE, 3427985

  • Zeng Z, Wang L, Cao Y, Luo Y (2012) Synthesis of 2-amide-3-carboxylate-4-aryl-4H-chromene derivatives. Res Chem Intermed 38(8):1751–1760

    Article  Google Scholar 

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Acknowledgments

We gratefully acknowledge financial support from the Research Council of Tabriz Branch of Islamic Azad University.

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Correspondence to L. Edjlali.

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Edjlali, L., Hosseinzdeh-Khanmiri, R. γ-Alumina Catalyzed Green Synthesis of Pyran’s Annulated Heterocyclic Systems via Three-Component Reaction. Iran. J. Sci. Technol. Trans. Sci. 40, 151–156 (2016). https://doi.org/10.1007/s40995-016-0014-y

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  • DOI: https://doi.org/10.1007/s40995-016-0014-y

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