10.1007/s40097-014-0140-z

Efficient one-pot four-component synthesis of 1,4-dihydropyridines promoted by magnetite/chitosan as a magnetically recyclable heterogeneous nanocatalyst

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  • Ali Maleki*1,
  • Maryam Kamalzare1,
  • Morteza Aghaei1,
  1. Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, IR
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Published in Issue 10-12-2014

How to Cite

Maleki, A., Kamalzare, M., & Aghaei, M. (2014). Efficient one-pot four-component synthesis of 1,4-dihydropyridines promoted by magnetite/chitosan as a magnetically recyclable heterogeneous nanocatalyst. Journal of Nanostructure in Chemistry, 5(1 (March 2015). https://doi.org/10.1007/s40097-014-0140-z
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Abstract

Abstract 1,4-Dihydropyridines are synthesized from various aromatic aldehyde, dimedone or 1,3-cyclohexandione, ethyl acetoacetate or methyl acetoacetate and ammonium acetate catalyzed by magnetite/chitosan at room temperature under mild reaction conditions. This process offers an easy and efficient synthesis of 1,4-dihydropyridine derivatives in high yields. The benefits of this protocol are simplicity, nontoxicity, low cost, simple work-up, and an environmentally benign nature. The catalyst is recovered by filtration and reused at least five times without significant loss in catalytic activity.

Keywords

  • Nanocatalyst,
  • Multicomponent reactions,
  • Chitosan,
  • Fe3O4,
  • 1,4-dihydropyridine,
  • Heterogeneous
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References

  1. Gawande et al. (2013) The rise of magnetically recyclable nanocatalysts (pp. 3371-3393) https://doi.org/10.1039/c3cs35480f
  2. Gawande et al. (2013) Nano-magnetite (Fe3O4) as a support for recyclable catalysts in the development of sustainable methodologies (pp. 3371-3393) https://doi.org/10.1039/c3cs35480f
  3. Wang and Astruc (2014) Fast-growing field of magnetically recyclable nanocatalysts (pp. 6949-6985) https://doi.org/10.1021/cr500134h
  4. Kainz et al. (2014) Palladium nanoparticles supported on magnetic carbon-coated cobalt nanobeads: highly active and recyclable catalysts for alkene hydrogenation (pp. 2020-2027) https://doi.org/10.1002/adfm.201303277
  5. Shelke et al. (2014) Iron oxide-supported copper oxide nanoparticles (Nanocat-Fe-CuO): magnetically recyclable catalysts for the synthesis of pyrazole derivatives, 4-methoxyaniline, and Ullmann-type condensation reactions (pp. 1699-1706) https://doi.org/10.1021/sc500160f
  6. Sá et al. (2014) Magnetically recyclable magnetite–palladium (Nanocat-Fe–Pd) nanocatalyst for the Buchwald-Hartwig reaction (pp. 3494-3500) https://doi.org/10.1039/c4gc00558a
  7. Gawande et al. (2013) Magnetite-supported sulfonic acid: a retrievable nanocatalyst for the Ritter reaction and multicomponent reactions (pp. 1895-1899) https://doi.org/10.1039/c3gc40457a
  8. Shokouhimehr et al. (2007) A magnetically recyclable nanocomposite catalyst for olefin epoxidation (pp. 7039-7043) https://doi.org/10.1002/anie.200702386
  9. Shirini and Abedini (2013) Application of nanocatalysts in multi-component reactions (pp. 4838-4860) https://doi.org/10.1166/jnn.2013.7571
  10. Montazeri et al. (2013) Separation of the defect-free Fe3O4–Au core/shell fraction from magnetite-gold composite nanoparticles by an acid wash treatment (pp. 25-28) https://doi.org/10.1186/2193-8865-3-25
  11. Sausins and Duburs (1988) Synthesis of 1,4-dihydropyridines by cyclocondensation reactions (pp. 269-289) https://doi.org/10.3987/REV-87-370
  12. Gaudio et al. (1994) Quantitative structure-activity relationships for 1,4-dihydropyridine calcium channel antagonists (nifedipine analogues): a quantum chemical/classical approach (pp. 1110-1115) https://doi.org/10.1002/jps.2600830809
  13. Mager et al. (1992) QSAR, diagnostic statistics and molecular modelling of 1,4-dihydropyridine calcium antagonists: a difficult road ahead (pp. 273-289)
  14. Gordeev et al. (1996) Approaches to combinatorial synthesis of heterocycles: a solid-phase synthesis of 1,4-dihydropyridines (pp. 924-982) https://doi.org/10.1021/jo951706s
  15. Hantzsch (1882) Ueber die synthese pyridinartiger verbindungenaus acetessigäther und aldehyd ammoniak (pp. 1-82) https://doi.org/10.1002/jlac.18822150102
  16. Agarwal and Chauhan (2005) Solid supported synthesis of structurally diverse dihydropyrido[2,3-d]pyrimidines using microwave irradiation (pp. 1345-1348) https://doi.org/10.1016/j.tetlet.2004.12.109
  17. Ohberg and Westman (2001) An efficient and fast procedure for the Hantzsch dihydropyridine synthesis under microwave conditions (pp. 1296-1298) https://doi.org/10.1055/s-2001-16043
  18. Breitenbucher and Figliozzi (2000) Solid-phase synthesis of 4-aryl-1,4-dihydropyridines via the Hantzsch three component condensation (pp. 4311-4315) https://doi.org/10.1016/S0040-4039(00)00660-2
  19. Liang et al. (2002) Heterocyclic bibenzimidazole derivatives as topoisomerase I inhibitors (pp. 719-723) https://doi.org/10.1016/S0968-0896(01)00318-2
  20. Miri et al. (2002) Synthesis and calcium channel antagonist activities of 3-nitrooxyalkyl, 5-alkyl 1,4-dihydro-2,6-dimethyl-4-(1-methyl-5-nitro-2-imidazolyl)-3,5-pyridinedicarboxylates (pp. 123-128) https://doi.org/10.1016/S0014-827X(01)01183-1
  21. Dondoni et al. (2003) Model studies toward the synthesis of dihydropyrimidinyl and pyridyl α-amino acids via three-component biginelli and Hantzsch cyclocondensations (pp. 6172-6183) https://doi.org/10.1021/jo0342830
  22. Dondoni et al. (2004) Multicomponent Hantzsch cyclocondensation as a route to highly functionalized 2- and 4-dihydropyridylalanines, 2- and 4-pyridylalanines, and their n-oxides: preparation via a polymer-assisted solution-phase approach (pp. 2311-2326) https://doi.org/10.1016/j.tet.2004.01.011
  23. Ji et al. (2004) Facile ionic liquids-promoted one-pot synthesis of polyhydroquinoline derivatives under solvent free conditions (pp. 831-832) https://doi.org/10.1055/s-2004-820035
  24. Maheswara et al. (2006) An efficient one-pot synthesis of polyhydroquinoline derivatives via Hantzsch condensation using heterogeneous catalyst under solvent-free conditions (pp. 201-206)
  25. Chari and Syamasundar (2005) Silica gel/NaHSO4 catalyzed one-pot synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature (pp. 624-626) https://doi.org/10.1016/j.catcom.2005.03.010
  26. Ko et al. (2005) Molecular iodine-catalyzed one-pot synthesis of 4-substituted-1,4-dihydropyridine derivatives via Hantzsch reaction https://doi.org/10.1016/j.tetlet.2005.05.148
  27. Kumar and Maurya (2007) Bakers’ yeast catalyzed synthesis of polyhydroquinoline derivatives via an unsymmetrical Hantzsch reaction (pp. 3887-3890) https://doi.org/10.1016/j.tetlet.2007.03.130
  28. Wang et al. (2005) Facile Yb(OTf)3 promoted one-pot synthesis of polyhydroquinoline derivatives through Hantzsch reaction (pp. 1539-1543) https://doi.org/10.1016/j.tet.2004.11.079
  29. Tewari et al. (2004) Tetrabutylammonium hydrogen sulfate catalyzed eco-friendly and efficient synthesis of glycosyl 1,4-dihydropyridines (pp. 9011-9014) https://doi.org/10.1016/j.tetlet.2004.10.057
  30. Kumar and Maurya (2007) Synthesis of polyhydroquinoline derivatives through unsymmetric Hantzsch reaction using organocatalysts (pp. 1946-1952) https://doi.org/10.1016/j.tet.2006.12.074
  31. Cherkupally and Mekalan (2008) PTSA catalyzed facile and efficient synthesis of polyhydroquinoline derivatives through Hantzsch multi-component condensation (pp. 1002-1004) https://doi.org/10.1248/cpb.56.1002
  32. Adibi et al. (2007) Iron(III) trifluoroacetate and trifluorometh-anesulfonate: recyclable Lewis acid catalysts for one-pot synthesis of 3,4-dihydropyrimidinones or their sulfur analogues and 1,4-dihydropyridines via solvent-free Biginelli and Hantzsch condensation protocols (pp. 2119-2124) https://doi.org/10.1016/j.catcom.2007.04.022
  33. Sabitha et al. (2003) A novel TMSI-mediated synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature (pp. 4129-4131) https://doi.org/10.1016/S0040-4039(03)00813-X
  34. Sapkal et al. (2009) Nickel nanoparticle-catalyzed facile and efficient one-pot synthesis of polyhydroquinoline derivatives via Hantzsch condensation under solvent-free conditions (pp. 1754-1756) https://doi.org/10.1016/j.tetlet.2009.01.140
  35. Sheldon (2012) Fundamentals of green chemistry: efficiency in reaction design (pp. 1437-1451) https://doi.org/10.1039/C1CS15219J
  36. Walsh et al. (2007) A green chemistry approach to asymmetric catalysis: solvent-free and highly concentrated reactions (pp. 2503-2545) https://doi.org/10.1021/cr0509556
  37. NasirBaig and Varma (2012) Stereo- and regio-selective one-pot synthesis of triazole-based unnatural amino acids and β-amino triazoles (pp. 5853-5855) https://doi.org/10.1039/c2cc32392c
  38. NasirBaig and Varma (2012) Alternative energy input: mechanochemical, microwave and ultrasound-assisted organic synthesis (pp. 1559-1584) https://doi.org/10.1039/C1CS15204A
  39. Gawande et al. (2012) Nanocatalysis and prospects of green chemistry (pp. 65-68) https://doi.org/10.1002/cssc.201100377
  40. Maleki (2012) Fe3O4/SiO2 nanoparticles: an efficient and magnetically recoverable nanocatalyst for the one-pot multicomponent synthesis of diazepines (pp. 7827-7829) https://doi.org/10.1016/j.tet.2012.07.034
  41. Maleki (2013) One-pot multicomponent synthesis of diazepine derivatives using terminal alkynes in the presence of silica-supported superparamagnetic iron oxide nanoparticles (pp. 2055-2059) https://doi.org/10.1016/j.tetlet.2013.01.123
  42. Maleki et al. (2014) Chitosan-supported Fe3O4 nanoparticles: a magnetically recyclable heterogeneous nanocatalyst for the syntheses of multifunctional benzimidazoles and benzodiazepines (pp. 9416-9423) https://doi.org/10.1039/c3ra47366j
  43. Maleki and Kamalzare (2014) Fe3O4@cellulose composite nanocatalyst: preparation, characterization and application in the synthesis of benzodiazepines (pp. 67-71) https://doi.org/10.1016/j.catcom.2014.05.004
  44. Maleki et al. (2014) Synthesis and characterization of magnetic bromochromate hybrid nanomaterials with triphenylphosphine surface-modified iron oxide nanoparticles and their catalytic application in multicomponent reactions (pp. 29765-29771) https://doi.org/10.1039/C4RA04654D
  45. Tajbakhsh et al. (2013) Proticpyridinium ionic liquid as a green and highly efficient catalyst for the synthesis of polyhydroquinoline derivatives via Hantzsch condensation in water (pp. 44-48) https://doi.org/10.1016/j.molliq.2012.09.017
  46. Song et al. (2010) One-pot synthesis of hexahydroquinolines via Hantzsch four-component reaction catalyzed by a cheap amino alcohol (pp. 3067-3077) https://doi.org/10.1080/00397910903370626
  47. Zare et al. (2013) Synthesis, characterization and application of ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient catalyst for the preparation of hexahydroquinolines (pp. 113-121) https://doi.org/10.1016/j.molliq.2012.10.045
  48. Safari et al. (2011) Cobalt nanoparticles promoted highly efficient one pot four-component synthesis of 1,4-dihydropyridines under solvent-free conditions (pp. 1850-1855) https://doi.org/10.1016/S1872-2067(10)60295-1
  49. Heravi et al. (2010) Brønsted acid ionic liquid [(CH2)4SO3HMIM][HSO4] as novel catalyst for one-pot synthesis of Hantzsch polyhydroquinoline derivatives (pp. 523-529) https://doi.org/10.1080/00397910902994194
  50. Singh and Singh (2010) Glycine-catalyzed easy and efficient one-pot synthesis of polyhydroquinolines through Hantzsch multicomponent condensation under controlled microwave (pp. 194-198)
  51. Surasani et al. (2012) FeF3 as a novel catalyst for the synthesis of polyhydroquinoline derivatives via unsymmetrical Hantzsch reaction (pp. 91-96) https://doi.org/10.1016/j.jfluchem.2011.09.005
  52. Peng et al. (2011) p-Toluene sulfonic acid catalyzed one-pot synthesis of unsymmetrical 1,4-dihydropyridines derivatives via Hantzsch reaction (pp. 1833-1837)
  53. Yang et al. (2011) Synthesis and antioxidant evaluation of novel 4-aryl-hexahydroquinolines from lignin (pp. 327-329)
  54. Hong et al. (2010) Hafnium (IV) bis(perfluorooctanesulfonyl)imide complex catalyzed synthesis of polyhydroquinoline derivatives via unsymmetrical Hantzsch reaction in fluorous medium (pp. 111-114) https://doi.org/10.1016/j.jfluchem.2009.10.009
  55. Li et al. (2012) DPTA-catalyzed one-pot regioselective synthesis of polysubstituted pyridines and 1,4-dihydropyridines (pp. 4138-4144) https://doi.org/10.1016/j.tet.2012.03.104
  56. Mohammadi et al. (2012) FeNH4(SO4)2·12H2O (alum)-catalyzed preparation of 1,4-dihydropyridines: improved conditions for the Hantzsch reaction (pp. 931-933) https://doi.org/10.1007/s00706-011-0672-6
  57. Qin et al. (2010) Silica sulfuric acid: an efficient and versatile catalyst for one-pot synthesis of substituted 5-oxo-1,4,5,6,7,8-hexahydroquinoline derivatives (pp. 1179-1182)
  58. Nasr-Esfahani and Abdizadeh (2012) Vanadatesulfuric acid-catalyzed novel and eco-benign one-pot synthesis of polyhydroquinoline derivatives under solvent-free conditions (pp. 1249-1258) https://doi.org/10.13005/ojc/280321
  59. Sainani et al. (1994) Synthesis of 4-aryl-1,4,5,6,7,8-hexahydro-5-oxo- 2,7,7-trimehyl-quinoline-3-carboxylates and amides (pp. 526-531)