Skip to main content
SpringerLink
Log in

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

  • Regular Article
  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Figure 1
Figure 2
Figure 3
Figure 4
Scheme 1
Scheme 2
Scheme 3
Scheme 4

Similar content being viewed by others

References

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

    CAS  Google Scholar 

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

    Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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 

Download references

Acknowledgements

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

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Sabzevar, Sabzevar, Iran

    SEYEDEH FATEMEH HOJATI & NASRIN MOEINIEGHBALI

  2. Department of chemistry, University of Maragheh, Maragheh, Iran

    MARYAM MOOSAVIFAR

Authors
  1. SEYEDEH FATEMEH HOJATI
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. MARYAM MOOSAVIFAR
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. NASRIN MOEINIEGHBALI
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to SEYEDEH FATEMEH HOJATI.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

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

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s12039-020-1736-0

Keywords

Search

Navigation