10.1186/2193-8865-3-85

CuO-CeO2 nanocomposite catalyzed efficient synthesis of aminochromenes

  1. College of Science, Behbahan Khatam Alanbia University of Technology, Behbahan, IR
  2. Catalysis and Reaction Engineering, Tehran University, Tehran, IR
  3. Department of Chemistry, Gachsaran Branch, Islamic Azad University, Gachsaran, IR
Cover Image

Published in Issue 18-11-2013

How to Cite

Albadi, J., Razeghi, A., Mansournezhad, A., & Azarian, Z. (2013). CuO-CeO2 nanocomposite catalyzed efficient synthesis of aminochromenes. Journal of Nanostructure in Chemistry, 3(1 (December 2013). https://doi.org/10.1186/2193-8865-3-85

HTML views: 33

PDF views: 86

Abstract

Abstract CuO-CeO 2 nanocomposite is reported as an efficient and green recyclable catalyst for the synthesis of chromene derivatives under solvent-free conditions. The catalyst was synthesized by co-precipitation method and characterized by X-ray diffraction, Brenauer-Emmett-Teller specific surface area, FESEM and energy dispersive spectroscopy analysis. This catalyst can be recovered by simple filtration and recycled up to 10 consecutive runs without loss of its activity. This process provides some advantages such as simple work-up, clean procedure, short reaction times and high yields of the products.

Keywords

  • CuO-CeO2 nanocomposite,
  • Aminochromenes,
  • Resorcinol,
  • Malononitrile,
  • Solvent-free conditions

References

  1. Banerjee and Sereda (2009) One-step, three-component synthesis of highly substituted pyridines using silica nanoparticle as reusable catalyst (pp. 6959-6992) https://doi.org/10.1016/j.tetlet.2009.09.137
  2. Astruc (2008) Wiley-VCH
  3. Sharghi and Hosseini (2002) Solvent-free and one step Beckman rearrangement of Ketones and aldehydes by zinc oxide (pp. 1057-1059)
  4. Hosseini and Sharghi (2004) Reactions on a solid surface. A simple, economical and efficient Friedel-Crafts acylation reaction over zinc oxide (ZnO) as a new catalyst (pp. 6953-6956) https://doi.org/10.1021/jo0494477
  5. Yin et al. (2004) Magnesia-carbon nanotubes (MgO–CNTs) nanocomposite: novel support of Ru catalyst for the generation of COx-free hydrogen from ammonia (pp. 113-116) https://doi.org/10.1023/B:CATL.0000030107.64702.74
  6. Drexler and Amiridis (2002) Kinetic investigation of the heterogeneous synthesis of flavanone over MgO (pp. 175-181) https://doi.org/10.1023/A:1015320711566
  7. Varma (1999) Solvent-free organic syntheses, using supported reagents and microwave irradiation (pp. 43-55) https://doi.org/10.1039/a808223e
  8. Samantaray et al. (2012) Catalytic application of CeO2-CaO nanocomposite oxide synthesized using amorphous citrate process toward the aqueous phase one pot synthesis of 2-amino-2-chromenes (pp. 1-9) https://doi.org/10.1016/j.cej.2012.04.011
  9. Li et al. (2012) One-pot solvothermal synthesis of Pd/Fe3O4 nanocomposite and its magnetically recyclable and efficient catalysis for Suzuki reactions (pp. 81-87) https://doi.org/10.1016/j.molcata.2012.03.025
  10. Kidwai et al. (2005) Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents (pp. 4295-4298) https://doi.org/10.1016/j.bmcl.2005.06.041
  11. Dekamin et al. (2013) Potassium phthalimide-N-oxyl: a novel, efficient, and simple organocatalyst for the one-pot three-component synthesis of various 2-amino-4H-chromene derivatives in water (pp. 1074-1085) https://doi.org/10.1016/j.tet.2012.11.068
  12. Naimi-Jamal et al. (2010) An efficient, multicomponent approach for solvent-free synthesis of 2-amino-4H-chromene scaffold (pp. 437-477) https://doi.org/10.1007/s11030-010-9246-5
  13. Khurana et al. (2010) DBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b]pyranes, 2-amino-4Hbenzo[h]chromenes and 2-amino-4H benzo[g]chromenes in aqueous medium (pp. 5637-5641) https://doi.org/10.1016/j.tet.2010.05.082
  14. Jin et al. (2004) Ultrasound-assisted synthesis of 2-amino-2-chromenes with cetyltrimethylammonium bromide in aqueous media (pp. 393-397)
  15. Makarem et al. (2008) A multi-component electro-organic synthesis of 2-amino-4H-chromenes (pp. 7194-7196) https://doi.org/10.1016/j.tetlet.2008.10.006
  16. Dyachenko and Chernegam (2006) Aliphatic aldehydes in multicomponent syntheses of 4-alkyl-substituted partially hydrogenated quinolines, fused 4H-pyrans, and 2-amino-4-ethyl-5-methylbenzene-1,3-dicarbonitrile (pp. 567-576) https://doi.org/10.1134/S1070428006040142
  17. Mehrabi and Kazemi-Mireki (2011) An efficient and recyclable nanocatalyst for the rapid and green synthesis of 3,4-dihydropyrano[c]chromenes (pp. 1419-1422) https://doi.org/10.1016/j.cclet.2011.06.003
  18. Maggi et al. (2004) Basic alumina catalysed synthesis of substituted 2-amino-2-chromenes via three-component reaction (pp. 2297-2299) https://doi.org/10.1016/j.tetlet.2004.01.115
  19. Shestopalov et al. (2002) One_step synthesis of substituted 2-amino-4H-chromenes and 2-amino-4H-benzo[f]chromenes. Molecular and crystal structure of 2-amino-3-cyano-6-hydroxy-4-phenyl-4H-benzo[f]chromene (pp. 2238-2241) https://doi.org/10.1023/A:1022135402451
  20. Banothu and Bavanthula (2012) Brønsted acidic ionic liquid catalyzed highly efficient synthesis of chromeno pyrimidinone derivatives and their antimicrobial activity (pp. 1015-1018) https://doi.org/10.1016/j.cclet.2012.06.041
  21. Mohammadzadeh and Sheibani (2012) A convenient one-pot synthesis of new chromeno[3,4-c]chromene and chromeno[3,4-c]pyridine derivatives in the presence of high surface area of magnesium oxide (pp. 1327-1330) https://doi.org/10.1016/j.cclet.2012.10.007
  22. Mobinikhaledi et al. (2011) Microwave-assisted one-pot synthesis of 2-amino-2-chromenes using piperazine as a catalyst under solvent-free conditions (pp. 262-265)
  23. Eshghi et al. (2011) Efficient one-pot synthesis of 2-amino-4H- chromenes catalyzed by ferric hydrogen sulfate and Zr-based catalysts of FI (pp. 1067-1073) https://doi.org/10.1080/15533174.2011.591347
  24. Raghuvanshi and Singh (2010) An expeditious synthesis of novel pyranopyridine derivatives involving chromenes under controlled microwave irradiation (pp. 305-317)
  25. Mosadegh (2013) Ultrasonic-assisted preparation of nano eggshell powder: a novel catalyst in green and high efficient synthesis of 2-aminochromenes (pp. 1436-1441) https://doi.org/10.1016/j.ultsonch.2013.04.008
  26. Gaikwad et al. (2011) An efficient multi-component synthesis of (2-amino-3-cyano-4H-chromen-4-yl) phosphonic acid diethyl ester (pp. 865-868) https://doi.org/10.1016/j.crci.2011.03.001
  27. Datta and Pasha (2012) Glycine catalyzed convenient synthesis of 2-amino-4H-chromenes in aqueous medium under sonic condition (pp. 725-728) https://doi.org/10.1016/j.ultsonch.2012.01.006
  28. Albadi et al. (2013) CuO-CeO2 nanocomposite: an efficient recyclable catalyst for the synthesis of aryl-14H-dibenzo[a-j]xanthenes (pp. 1-8) https://doi.org/10.1155/2013/546194
  29. Albadi et al. (2013) CuO–CeO2 nanocomposite: a highly efficient recyclable catalyst for the multicomponent synthesis of 4H-benzo[b]pyran derivatives (pp. 821-824) https://doi.org/10.1016/j.cclet.2013.05.031
  30. Albadi et al. (2013) Poly(4-vinylpyridine): as a green, efficient and commercial available basic catalyst for the synthesis of chromene derivatives (pp. 208-210) https://doi.org/10.1016/j.cclet.2013.01.020