10.1007/s40097-020-00361-x

Chitosan magnetic nanocomposite: a magnetically reusable nanocatalyst for green synthesis of Hantzsch 1,4-dihydropyridines under solvent-free conditions

  • Parichehr Kamalzare1,
  • Behrooz Mirza1,
  • Somayeh Soleimani-Amiri*1,
  1. Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, IR

Published in Issue 23-10-2020

How to Cite

Kamalzare, P., Mirza, B., & Soleimani-Amiri, S. (2020). Chitosan magnetic nanocomposite: a magnetically reusable nanocatalyst for green synthesis of Hantzsch 1,4-dihydropyridines under solvent-free conditions. Journal of Nanostructure in Chemistry, 11(2 (June 2021). https://doi.org/10.1007/s40097-020-00361-x
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Abstract

Abstract An environmentally friendly method for the efficient synthesis of biologically active 1,4-dihydropyridine derivatives has been performed. The reaction was carried out under solvent-free conditions using chitosan magnetic nanocomposite of Ch-Rhomboclase as an efficient heterogeneous recyclable catalyst. The chitosan magnetic nanocomposite was synthesized through a comfortable and reasonably priced method. It was specified by FT-IR, XRD, EDS, SEM, TEM, VSM, and TGA analyses. Mild reaction conditions, absence of toxic solvent, low catalyst loading, high speed and efficiency, magnetically removable catalyst, and reusability of catalyst are the most important advantages of this method for the synthesis of Hantzsch 1,4-dihydropyridines. Graphic abstract

References

  1. Klusa (1995) Cerebrocrast. Neuroprotectant, cognition enhancer 20(2) (pp. 135-138) https://doi.org/10.1358/dof.1995.020.02.284117
  2. Bretzel et al. (1993) Nephroprotective effects of nitrendipine in hypertensive tune I and type II diabetic patients 21(6) (pp. S53-S64) https://doi.org/10.1016/0272-6386(93)70125-I
  3. Cariou et al. (2008) Rapid synthesis of 1,3,4,4-tetrasubstituted β-lactams from methyleneaziridines using a four-component reaction 73(24) (pp. 9762-9764) https://doi.org/10.1021/jo801664g
  4. Aute, D., Kshirsagar, A., Uphade, B., Gadhave, A.: Ultrasound Assisted and Aluminized Polyborate Prompted Green and Efficient One Pot Protocol for the Synthesis of Hexahydroquinolines. Polycycl. Aromat. Compd. (2020).
  5. https://doi.org/10.1080/10406638.2020.1781206
  6. Mekheimer et al. (2008) Solar thermochemical reactions: four-component synthesis of polyhydroquinoline derivatives induced by solar thermal energy 10(5) (pp. 592-593) https://doi.org/10.1039/b715126h
  7. Donelson et al. (2006) An efficient one-pot synthesis of polyhydroquinoline derivatives through the Hantzsch four component condensation 256(1) (pp. 309-311) https://doi.org/10.1016/j.molcata.2006.03.079
  8. Hong et al. (2010) Hafnium (IV) bis(perfluorooctanesulfonyl)imide complex catalyzed synthesis of polyhydroquinoline derivatives via unsymmetrical Hantzsch reaction in fluorous medium 131(1) (pp. 111-114) https://doi.org/10.1016/j.jfluchem.2009.10.009
  9. Evans and Gestwicki (2009) Enantioselective organocatalytic hantzsch synthesis of polyhydroquinolines 11(14) (pp. 2957-2959) https://doi.org/10.1021/ol901114f
  10. Sapkal et al. (2009) Nickel nanoparticle-catalyzed facile and efficient one-pot synthesis of polyhydroquinoline derivatives via Hantzsch condensation under solvent-free conditions 50(15) (pp. 1754-1756) https://doi.org/10.1016/j.tetlet.2009.01.140
  11. Singh and Singh (2010) Glycine-catalyzed easy and efficient one-pot synthesis of polyhydroquinolines through Hantzsch multicomponent condensation under controlled microwave 47(1) (pp. 194-198)
  12. Sheik Mansoor et al. (2017) An efficient one-pot multi component synthesis of polyhydroquinoline derivatives through Hantzsch reaction catalysed by Gadolinium triflate (pp. 546-553) https://doi.org/10.1016/j.arabjc.2012.10.017
  13. Rekunge et al. (2017) Sulfated polyborate: An efficient and reusable catalyst for one pot synthesis of Hantzsch 1,4-dihydropyridines derivatives using ammonium carbonate under solvent free conditions 58(12) (pp. 1240-1244) https://doi.org/10.1016/j.tetlet.2017.02.038
  14. Davoodnia et al. (2013) Tetrabutylammonium hexatungstate [TBA]2[W6O19]: Novel and reusable heterogeneous catalyst for rapid solvent-free synthesis of polyhydroquinoline via unsymmetrical Hantzsch reaction 34(6) (pp. 1173-1178) https://doi.org/10.1016/S1872-2067(12)60547-6
  15. Davarpanah et al. (2019) Synthesis of 1,4-dihydropyridine and polyhydroquinoline derivatives via Hantzsch reaction using nicotinic acid as a green and reusable catalyst (pp. 525-535) https://doi.org/10.1016/j.molstruc.2018.10.002
  16. Aute et al. (2020) Aluminized polyborate-catalysed green and efficient synthesis of polyhydroquinolines under solvent-free conditions 46(7) (pp. 3491-3508) https://doi.org/10.1007/s11164-020-04158-z
  17. Dharma Rao et al. (2017) Solvent-free synthesis of polyhydroquinoline derivatives employing mesoporous vanadium ion doped titania nanoparticles as a robust heterogeneous catalyst via the Hantzsch reaction 7(6) (pp. 3611-3616) https://doi.org/10.1039/C6RA26664A
  18. Astruc et al. (2005) Nanoparticles as recyclable catalysts: the frontier between homogeneous and heterogeneous catalysis 44(48) (pp. 7852-7872) https://doi.org/10.1002/anie.200500766
  19. Zeng et al. (2010) Fe3O4 nanoparticles: a robust and magnetically recoverable catalyst for three-component coupling of aldehyde, alkyne and amine 12(4) (pp. 570-573) https://doi.org/10.1039/b920000b
  20. Zhang et al. (2011) Magnetic CuFe2O4 nanoparticles as an efficient catalyst for C-O cross-coupling of phenols with aryl halides 3(1) (pp. 146-149) https://doi.org/10.1002/cctc.201000254
  21. Nasr-Esfahani et al. (2011) Fe3O4 nanoparticles as an efficient and magnetically recoverable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions 32(9) (pp. 1484-1489) https://doi.org/10.1016/S1872-2067(10)60263-X
  22. Ghavidel et al. (2019) A novel, efficient, and recoverable basic Fe3O4@C nano-catalyst for green synthesis of 4H-chromenes in water via one-pot three component reactions (pp. 1-22)
  23. Ghavidel et al. (2020) New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4H-chromenes using magnetic nanoparticle catalyst (pp. 1-21)
  24. Samiei et al. (2020) Fe3O4@C@OSO3H as an efficient, recyclable magnetic nanocatalyst in Pechmann condensation: green synthesis, characterization, and theoretical study (pp. 1-21)
  25. Taheri Hatkehlouei et al. (2020) Solvent-free one-pot synthesis of diverse dihydropyrimidinones/tetrahydropyrimidinones using biginelli reaction catalyzed by Fe3O4@C@OSO3H (pp. 1-17) https://doi.org/10.1080/10406638.2020.1781203
  26. Soleimani-Amiri et al. (2018) Synthesis of chromene derivatives via three-component reaction of 4-hydroxycumarin catalyzed by magnetic Fe3O4 nanoparticles in water 55(1) (pp. 209-213) https://doi.org/10.1002/jhet.3028
  27. Nasr-Esfahani et al. (2014) Magnetic Fe3O4 nanoparticles: efficient and recoverable nanocatalyst for the synthesis of polyhydroquinolines and Hantzsch 1,4-dihydropyridines under solvent-free conditions (pp. 99-105) https://doi.org/10.1016/j.molcata.2013.11.010
  28. Koukabi et al. (2011) Hantzsch reaction on free nano-Fe2O3 catalyst: excellent reactivity combined with facile catalyst recovery and recyclability 47(32) (pp. 9230-9232)
  29. Khazaei et al. (2018) Anchoring high density sulfonic acid based ionic liquid on the magnetic nano-magnetite (Fe3O4), application to the synthesis of hexahydroquinoline derivatives (pp. 484-494) https://doi.org/10.1016/j.molliq.2018.04.125
  30. Ravikumar Naik and Shivashankar (2016) Heterogeneous bimetallic ZnFe2O4 nanopowder catalyzed synthesis of Hantzsch 1,4-dihydropyridines in water 57(36) (pp. 4046-4049) https://doi.org/10.1016/j.tetlet.2016.07.071
  31. Maleki et al. (2015) Efficient one-pot four-component synthesis of 1,4-dihydropyridines promoted by magnetite/chitosan as a magnetically recyclable heterogeneous nanocatalyst 5(1) (pp. 95-105) https://doi.org/10.1007/s40097-014-0140-z
  32. Ashraf et al. (2020) New copper complex on Fe3O4 nanoparticles as a highly efficient reusable nanocatalyst for synthesis of polyhydroquinolines in water 150(3) (pp. 683-701) https://doi.org/10.1007/s10562-019-02986-2
  33. Hashemi-Uderji et al. (2019) Fe3O4@FSM-16-SO3H as a novel magnetically recoverable nanostructured catalyst: preparation, characterization and catalytic application 26(2) (pp. 467-480) https://doi.org/10.1007/s10934-018-0628-x
  34. Valadi et al. (2020) Ultrasound-assisted synthesis of 1,4-dihydropyridine derivatives by an efficient volcanic-based hybrid nanocomposite https://doi.org/10.1016/j.solidstatesciences.2020.106141
  35. Mirfarjood et al. (2017) Copper-incorporated fluorapatite encapsulated iron oxide nanocatalyst for synthesis of benzimidazoles 7(4) (pp. 359-366) https://doi.org/10.1007/s40097-017-0245-2
  36. Saadati-Moshtaghin and Zonoz (2017) Synthesis and characterization of magnetically recoverable 1-(copperferritesiloxypropyl)-3-methylimidazolium heteropolytungstate ionic liquid as a new nanocatalyst for the preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones 7(4) (pp. 317-325) https://doi.org/10.1007/s40097-017-0241-6
  37. Aguilera et al. (2019) Carboxymethyl cellulose coated magnetic nanoparticles transport across a human lung microvascular endothelial cell model of the blood–brain barrier 1(2) (pp. 671-685) https://doi.org/10.1039/C8NA00010G
  38. Safari and Javadian (2014) Chitosan decorated Fe3O4 nanoparticles as a magnetic catalyst in the synthesis of phenytoin derivatives 4(90) (pp. 48973-48979) https://doi.org/10.1039/C4RA06618A
  39. Rakhtshah and Yaghoobi (2019) Catalytic application of new manganese Schiff-base complex immobilized on chitosan-coated magnetic nanoparticles for one-pot synthesis of 3-iminoaryl-imidazo[1,2-a]pyridines (pp. 904-916) https://doi.org/10.1016/j.ijbiomac.2019.08.054
  40. Safari and Javadian (2015) Ultrasound assisted the green synthesis of 2-amino-4H-chromene derivatives catalyzed by Fe3O4-functionalized nanoparticles with chitosan as a novel and reusable magnetic catalyst (pp. 341-348) https://doi.org/10.1016/j.ultsonch.2014.02.002
  41. Motahharifar et al. (2020) Magnetic chitosan-copper nanocomposite: A plant assembled catalyst for the synthesis of amino- and N-sulfonyl tetrazoles in eco-friendly media https://doi.org/10.1016/j.carbpol.2019.115819
  42. Leonhardt et al. (2010) Chitosan as a support for heterogeneous Pd catalysts in liquid phase catalysis 379(1) (pp. 30-37) https://doi.org/10.1016/j.apcata.2010.02.029
  43. Muzzarelli (2011) Potential of chitin/chitosan-bearing materials for uranium recovery: an interdisciplinary review 84(1) (pp. 54-63) https://doi.org/10.1016/j.carbpol.2010.12.025
  44. Antony et al. (2013) Synthesis, spectrochemical characterisation and catalytic activity of transition metal complexes derived from Schiff base modified chitosan (pp. 423-430) https://doi.org/10.1016/j.saa.2012.09.101
  45. Baran et al. (2015) Synthesis and characterization of water soluble O-carboxymethyl chitosan Schiff bases and Cu(II) complexes (pp. 94-103) https://doi.org/10.1016/j.ijbiomac.2014.07.029
  46. Zhu et al. (2012) Synthesis of novel magnetic chitosan supported protonated peroxotungstate and its catalytic performance for oxidation 36(12) (pp. 2587-2592) https://doi.org/10.1039/c2nj40753a
  47. Asghari-Haji et al. (2017) Cobalt ferrite encapsulated in a zwitterionic chitosan derived shell: An efficient nano-magnetic catalyst for three-component syntheses of pyrano[3,2-c]quinolines and spiro-oxindoles 31(12) https://doi.org/10.1002/aoc.3891
  48. Moghadam et al. (2020) New nanomagnetic heterogeneous cobalt catalyst for the synthesis of aryl nitriles and biaryls 5(30) (pp. 18619-18627) https://doi.org/10.1021/acsomega.0c01002
  49. Veisi et al. (2020) In situ decorated Pd NPs on chitosan-encapsulated Fe3O4/SiO2-NH2 as magnetic catalyst in Suzuki-Miyaura coupling and 4-nitrophenol reduction https://doi.org/10.1016/j.carbpol.2020.115966
  50. Mohammadi and Kassaee (2013) Sulfochitosan encapsulated nano-Fe3O4 as an efficient and reusable magnetic catalyst for green synthesis of 2-amino-4H-chromen-4-yl phosphonates (pp. 152-158) https://doi.org/10.1016/j.molcata.2013.09.027
  51. Cremlyn, R.J.: Chlorosulfonic Acid: A Versatile Reagent. The Royal Society of Chemistry, pp. 1–6.(2002)
  52. Hyde et al. (2011) Methods to analyze metastable and microparticulate hydrated and hydrous iron sulfate minerals 96(11–12) https://doi.org/10.2138/am.2011.3792
  53. Mahinpour et al. (2018) New synthetic method for the synthesis of 1,4-dihydropyridine using aminated multiwalled carbon nanotubes as high efficient catalyst and investigation of their antimicrobial properties 22(7) (pp. 876-885) https://doi.org/10.1016/j.jscs.2017.11.001
  54. Allahresani et al. (2020) CoFe2O4@SiO2-NH2-CoII NPs catalyzed Hantzsch reaction as an efficient, reusable catalyst for the facile, green, one-pot synthesis of novel functionalized 1,4-dihydropyridine derivatives 34(9) https://doi.org/10.1002/aoc.5759
  55. Igder et al. (2015) Melamine supported on hydroxyapatite-encapsulated-γ-Fe2O3: a novel superparamagnetic recyclable basic nanocatalyst for the synthesis of 1,4-dihydropyridines and polyhydroquinolines 41(10) (pp. 7227-7244) https://doi.org/10.1007/s11164-014-1808-1
  56. Khodamorady et al. (2020) Efficient one-pot synthetic methods for the preparation of 3,4-dihydropyrimidinones and 1,4-dihydropyridine derivatives using BNPs@SiO2(CH2)3NHSO3H as a ligand and metal free acidic heterogeneous nano-catalyst https://doi.org/10.1016/j.poly.2019.114340
  57. Maleki et al. (2018) Magnetic guanidinylated chitosan nanobiocomposite: a green catalyst for the synthesis of 1,4-dihydropyridines (pp. 320-326) https://doi.org/10.1016/j.ijbiomac.2018.05.035
  58. Maleki et al. (2019) Cellulose matrix embedded copper decorated magnetic bionanocomposite as a green catalyst in the synthesis of dihydropyridines and polyhydroquinolines (pp. 251-260) https://doi.org/10.1016/j.carbpol.2018.12.069
  59. Koukabi et al. (2012) A magnetic particle-supported sulfonic acid catalyst: tuning catalytic activity between homogeneous and heterogeneous catalysis 354(10) (pp. 2001-2008) https://doi.org/10.1002/adsc.201100352
  60. Ghosh et al. (2013) Hantzsch 1,4-dihydropyridine synthesis in aqueous ethanol by visible light 54(1) (pp. 58-62) https://doi.org/10.1016/j.tetlet.2012.10.079
  61. Coburn et al. (1988) 1,4-Dihydropyridine antagonist activities at the calcium channel: a quantitative structure-activity relationship approach 31(11) (pp. 2103-2107) https://doi.org/10.1021/jm00119a009
  62. Mirzaei and Davoodnia (2012) Microwave assisted sol-gel synthesis of MgO nanoparticles and their catalytic activity in the synthesis of Hantzsch 1,4-dihydropyridines 33(9) (pp. 1502-1507) https://doi.org/10.1016/S1872-2067(11)60431-2
  63. Yarhosseini et al. (2016) Tetraethylammonium 2-(carbamoyl)benzoate as a bifunctional organocatalyst for one-pot synthesis of Hantzsch 1,4-dihydropyridine and polyhydroquinoline derivatives 147(10) (pp. 1779-1787) https://doi.org/10.1007/s00706-016-1666-1
  64. Niaz et al. (2015) Synthesis of diethyl 4-substituted-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylates as a new series of inhibitors against yeast α-glucosidase (pp. 199-209) https://doi.org/10.1016/j.ejmech.2015.03.018
  65. Vahdat et al. (2019) Sulfonated organic heteropolyacid salts as a highly efficient and green solid catalysts for the synthesis of 1,8-dioxo-decahydroacridine derivatives in water 12(7) (pp. 1515-1521) https://doi.org/10.1016/j.arabjc.2014.10.026
  66. Ziarani et al. (2014) Synthesis of 1,8-dioxo-decahydroacridine derivatives using sulfonic acid functionalized silica (SiO2-Pr-SO3H) under solvent free conditions 7(3) (pp. 335-339) https://doi.org/10.1016/j.arabjc.2011.01.037
  67. Patil et al. (2014) Novel Brønsted acidic ionic liquid ([CMIM][CF3COO]) prompted multicomponent Hantzsch reaction for the eco-friendly synthesis of acridinediones: an efficient and recyclable catalyst 144(5) (pp. 949-958) https://doi.org/10.1007/s10562-014-1202-z