One-pot three-component synthesis of 1,8-dioxooctahydroxanthenes and 14-Aryl-14Hdibenzo[a,j]xanthenes using a new nanostructure zeolite

Abstract

A new modified zeolite containing Fe nanoparticles loaded in zeolite X (Fe-X) has been synthesized and characterized by FT-IR, XRD, EDX and SEM techniques and its catalytic activity has been investigated in the synthesis of two series of xanthene derivatives. We have described an efficient and novel method using Fe-X as a new and reusable catalyst for the synthesis of 1,8-dioxooctahydroxanthenes and 14-aryl-14H-dibenzo[a,j]xanthenes derivatives from one-pot three-component condensation of aromatic aldehyde and dimedone or β-naphthol under solvent-free conditions. The significant advantages of the present method are high yields of products, short reaction time, easy separation of the catalyst from the reaction mixture, easy product isolation, solvent-free condition and reusability of the catalyst.

Graphic abstract

A new modified zeolite containing Fe nanoparticles loaded in zeolite X has been synthesized, characterized and applied in the synthesis of two series of xanthene derivatives.

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References

  1. 1.

    Sersale R 1985 Natural zeolites: processing, present and possible applications Stud. Surf. Sci. Catal. 24 503

    CAS  Google Scholar 

  2. 2.

    Parveen A, Ahmed M R S, Shaikh K A, Deshmukh S P and Pawar R P 2007 Efficient synthesis of 2, 4, 5-triaryl substituted imidazoles under solvent free conditions at room temperature Arkivoc. 16 12

    Google Scholar 

  3. 3.

    Breck D W 1974 Zeolite Molecular Sieves (New York: Wiley)

    Google Scholar 

  4. 4.

    Flanigen E M 1991 Zeolites and molecular sieves: an historical perspective Stud. Surf. Sci. Catal. 58 13

    CAS  Google Scholar 

  5. 5.

    Choi E Y, Kim Y, Han Y W and Seff K 2000 Structure of a cyclopropane sorption complex of dehydrated fully Cd2+-exchanged zeolite A Micropor. Mesopor. Mat. 41 61

    CAS  Google Scholar 

  6. 6.

    Bae D and Seff K 1999 Structures of cobalt (II)-exchanged zeolite X Micropor. Mesopor. Mat. 33 265

    CAS  Google Scholar 

  7. 7.

    Sebastian J, Jinka K M and Jasra R V 2006 Effect of alkali and alkaline earth metal ions on the catalytic epoxidation of styrene with molecular oxygen using cobalt(II)-exchanged zeolite X J. Catal. 244 208

    CAS  Google Scholar 

  8. 8.

    Veljović E, Špirtović-Halilović S, Kahrović E, Roca S, Novaković I, Osmanović A, Salihović M, Alagić D, Hastor B, Ljubunćić Dž and Završnik D 2016 Solvent-free synthesis and antibacterial activity of 14-aryl substituted dibenzoxanthene derivatives Bull. Chem. Technol. Bosnia Herzegovina 46 33

    Google Scholar 

  9. 9.

    Naidu K R M, Krishna B S, Kumar M A, Arulselvan P, Khalivulla S I and Lasekan O 2012 Design, synthesis and antiviral potential of 14-aryl/heteroaryl-14H-dibenzo[a,j]xanthenes using an efficient polymer-supported catalyst Molecules 17 7543

    CAS  Google Scholar 

  10. 10.

    Poupelin J P, Saint-Rut G, Fussard-Blanpin O, Narcisse G, Uchida-Ernouf G and Lakroix R 1978 Synthesis and antiinflammatory properties of bis(2-hydroxy-1-naphthyl) methane derivatives. I. Monosubstituted derivatives Eur. J. Med. Chem. 13 67

    CAS  Google Scholar 

  11. 11.

    Chibale K, Visser M, Schalkwyk D V, Smith P J, Saravanamuthu A and Fairlamb A H 2003 Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents Tetrahedron 59 2289

    CAS  Google Scholar 

  12. 12.

    Saint-Ruf G, Hieu H T and Poupelin J P 1975 The effect of dibenzoxanthenes on the paralyzing action of zoxazolamine Naturwissenschaften 62 584

    CAS  PubMed  Google Scholar 

  13. 13.

    Peters A T and Bide M J 1985 Amino derivatives of 1,8-naphthalic anhydride and derived dyes for synthetic-polymer fibres Dyes Pigm. 6 349

    CAS  Google Scholar 

  14. 14.

    Ahmad M, King T A, Ko D K, Cha B H and Lee J 2002 Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases J. Phys. D: Appl. Phys. 35 1473

    CAS  Google Scholar 

  15. 15.

    Ion R M, Frackowiak D, Planner A and Wiktorowicz K 1998 The incorporation of various porphyrins into blood cells measured via flow cytometry, absorption and emission spectroscopy Acta Biochim. Pol. 45 833

    CAS  Google Scholar 

  16. 16.

    Knight C G and Stephens T 1989 Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles Biochem. J. 258 683

    CAS  PubMed  Google Scholar 

  17. 17.

    Das B, Thirupathi P, Reddy K R, Ravikanth B and Nagarapu L 2007 An efficient synthesis of 1,8-dioxooctahydroxanthenes using heterogeneous catalysts Catal. Commun. 8 535

    CAS  Google Scholar 

  18. 18.

    Madje B R, Ubale M B, Bharad J V and Shingare M S 2010 Alum-promoted synthesis of 1,8-dioxo-octahydroxanthenes in water Afr. J. Chem. 63 36

    Google Scholar 

  19. 19.

    Jin T S, Zhang J S, Xiao J C, Wang A Q and Li T S 2004 Clean synthesis of 1,8-dioxo-octahydroxanthene derivatives catalyzed by p-dodecylbenzenesulfonic acid in aqueous media ChemInform 35

  20. 20.

    Zhang Z H and Tao X Y 2008 2,4,6-Trichloro-1,3,5-triazine-promoted synthesis of 1,8-dioxo-octahydroxanthenes under solvent-free conditions Aust. J. Chem. 61 77

    CAS  Google Scholar 

  21. 21.

    Shaterian H R, Hosseinian A and Ghashang M 2008 Reaction in dry media: silica gel supported ferric chloride catalyzed synthesis of 1,8-dioxo-octahydroxanthene derivatives Phosphor. Sulfur Silicon. 183 3136

    CAS  Google Scholar 

  22. 22.

    Zhang Z H and Liu Y H 2008 Antimony trichloride/SiO2 promoted synthesis of 9-ary-3,4,5,6,7,9-hexahydroxanthene-1,8-diones Catal. Commun. 9 1715

    CAS  Google Scholar 

  23. 23.

    Kantevari S, Bantu R and Nagarapu L J 2007 HClO4–SiO2 and PPA–SiO2 catalyzed efficient one-pot Knoevenagel condensation, Michael addition and cyclo-dehydration of dimedone and aldehydes in acetonitrile, aqueous and solvent free conditions: Scope and limitations J. Mol. Catal. A Chem. 269 53

    CAS  Google Scholar 

  24. 24.

    Wu H, Chen X M, Wan Y, Xin H Q, Xu H H, Yue C H, Pang L L and Ma R 2009 Synthesis and Luminescence of 14-Aryl- or Alkyl-14H-dibenzo[a,j]xanthenes catalyzed by 2-1′-methylimidazolium-3-yl-1-ethyl sulfate Synth. Commun. 39 3762

    CAS  Google Scholar 

  25. 25.

    Das B, Ravikanth B, Ramu R, Laxminarayana K and Rao B V 2006 Iodine catalyzed simple and efficient synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j]xanthenes J. Mol. Catal. A: Chem. 255 74

    CAS  Google Scholar 

  26. 26.

    Mohammadpoor-Baltork I, Moghadam M, Mirkhani V, Tangestaninejad S and Tavakoli H R 2011 Highly efficient and green synthesis of 14-aryl(alkyl)-14H-dibenzo[a,j]xanthene and 1,8-dioxooctahydroxanthene derivatives catalyzed by reusable zirconyl triflate [ZrO(OTf))2] under solvent-free conditions Chin. Chem. Lett. 22 9

    CAS  Google Scholar 

  27. 27.

    Kumar P S, Kumar B S, Rajitha B, Reddy P N, Sreenivasulu N and Reddy Y T 2006 A novel one pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes catalyzed by SelectfluorTM under solvent free conditions Arkivoc. 12 46

    Google Scholar 

  28. 28.

    Dabiri M, Baghbanzadeh M, Nikcheh M S and Arzroomchilar E 2008 Eco-friendly and efficient one-pot synthesis of alkyl-or aryl-14H-dibenzo[a,j]xanthenes in water Bioorg. Med. Chem. Lett. 18 436

    CAS  Google Scholar 

  29. 29.

    Wu L, Zhang J, Fang L, Yang C and Yan F 2010 Silica chloride catalyzed synthesis of 14-aryl-14H-dibenzo[a,i]xanthene-8,13-diones Dyes Pigm. 86 93

    CAS  Google Scholar 

  30. 30.

    Baghbanian S M, Rezaei N and 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 3446

    CAS  Google Scholar 

  31. 31.

    Singhal R K, Gangadhar B, Basu H and Manisha V 2012 Remediation of malathion contaminated soil using zero valent iron nano-particles Am. J. Anal. Chem. 3 76

    CAS  Google Scholar 

  32. 32.

    Hojati S F, Amiri A and Raouf H 2017 Efficient four-component synthesis of spiroindole derivatives catalysed by a versatile and reusable nano-paramagnetic catalyst Appl. Organomet. Chem. 31 3595

    Google Scholar 

  33. 33.

    Hojati S F and Raouf H 2016 Ionic Liquid for One-pot Synthesis of Spiro [indoline-3,4′-pyrano[2,3-c]pyrazoles] Org. Prep. Proc. Int. 48 474

    CAS  Google Scholar 

  34. 34.

    Hojati S F, Moosavifar M and Ghorbanipoor T 2017 The improvement in nano composite host (nano cavity of dealuminated zeolite Y)-gest (12-molibdophosphoric acid) catalytic activity and its application in one-pot three-component synthesis of tetrahydrobenzo[b]pyrans C. R. Chem. 20 520

    CAS  Google Scholar 

  35. 35.

    Hojati S F, Amiri A, Mohamadi S and Moeini Eghbali N 2018 Novel organometallic nanomagnetic catalyst for multicomponent synthesis of spiroindoline derivatives Res. Chem. Int. 44 2275

    CAS  Google Scholar 

  36. 36.

    Hojati S F, Amiri A, MoeiniEghbali N and Mohamadi S 2018 Polypyrrole/Fe3O4/CNT as a recyclable and highly efficient catalyst for one-pot three-component synthesis of pyran derivatives Appl. Organomet. Chem. 32 4235

    Google Scholar 

  37. 37.

    Keshavarz M, Abdoli-Senejani M, Hojati S F and Moosavifar M 2017 Novel and highly efficient heteropoly acids for one-pot mild and green synthesis of xanthene derivatives Org. Prep. Proc. Int. 49 549

    CAS  Google Scholar 

  38. 38.

    Keshavarz M, Abdoli-Senejani M, Hojati S F and Askari S 2018 Fe3O4 magnetic nanoparticles coated with a copolymer: a novel reusable catalyst for one-pot three-component synthesis of 2-amino-4H-chromen React. Kin. Mech. Catal. 124 757

    CAS  Google Scholar 

  39. 39.

    Maleki B, Gholizadeh M and Bull Z 2011 1,3,5-Trichloro-2,4,6-triazinetrion: a versatile heterocycle for the one-pot synthesis of 14-aryl-or alkyl-14H-dibenzo[a,j]xanthene, 1,8-dioxooctahydroxanthene and 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one derivatives under solvent-free conditions Korean Chem. Soc. 32 1697

    CAS  Google Scholar 

  40. 40.

    Venkatesan K, Pujari S S, Lahoti R J and Srinivasan K V 2008 An efficient synthesis of 1,8-dioxo-octahydro-xanthene derivatives promoted by a room temperature ionic liquid at ambient conditions under ultrasound irradiation Ultrason. Sonochem. 15 548

    CAS  Google Scholar 

  41. 41.

    Zolfigol M A, Khakyzadeh V, Moosavi-Zare A R, Zare A, Azimi S B, Asgari Z and Hasaninejad A 2012 C. R. Chemie. 15 719

    CAS  Google Scholar 

  42. 42.

    Shirini F, Abedini M and Pourhasan R 2013 A novel polymeric and reusable catalyst for the preparation of xanthenes derivatives Dyes Pigm. 99 250

    CAS  Google Scholar 

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Acknowledgements

The author is grateful to the research council of Hakim Sabzevari University for partial support of this work.

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Correspondence to SEYEDEH FATEMEH HOJATI.

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HOJATI, S.F., MOOSAVIFAR, M. & MOEINIEGHBALI, N. One-pot three-component synthesis of 1,8-dioxooctahydroxanthenes and 14-Aryl-14Hdibenzo[a,j]xanthenes using a new nanostructure zeolite. J Chem Sci 132, 38 (2020). https://doi.org/10.1007/s12039-020-1736-0

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Keywords

  • Nanostructure zeolite X
  • one-pot synthesis
  • 1,8-dioxooctahydroxanthene
  • 14-aryl-14H-dibenzo[a,j]xanthene