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.
Similar content being viewed by others
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
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
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
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
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
Edjlali L (2008) The regiospecific synthesis of some new 3,5-disubstituted isoxazoles. J Chin Chem Soc 55(6):1322–1325
Fenn D (ed) (1994) The pyrimidines. Wiley, New York
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
Grieco PA (1998) Organic synthesis in water. Blackie, New York
Kidwai M, Jain A, Bhardwaj S (2012) Magnetic nanoparticles catalyzed synthesis of diverse N-Heterocycles. Mol Divers 16(1):121–128
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
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
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
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
Nagendrappa G (2002) Organic synthesis under solvent-free condition: an environmentally benign procedure-I. Resonance 7(10):59–68
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
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
Varma RS, Namboodiri VV (2001) Solvent-free preparation of ionic liquids using a household microwave oven. Pure Appl Chem 73(8):1309–1313
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
Acknowledgments
We gratefully acknowledge financial support from the Research Council of Tabriz Branch of Islamic Azad University.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s40995-016-0014-y