Skip to main content
SpringerLink
Log in

Synthesis of 1,8‐dioxo-octahydroxanthenes utilizing nanodiatomite@melamine-SO3H as a novel heterogeneous catalyst under solvent-free conditions

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

Abstract

A new heterogeneous catalyst, nanodiatomite@melamine-SO3H, was introduced for synthesizing 1,8‐dioxo-octahydroxanthenes via multicomponent reactions of aldehydes and dimedone. The prepared catalyst was characterized by employing several techniques, including FT-IR, XRD, TGA, EDX, BET, SEM, and TEM. The products were obtained under solvent-free conditions, with high yields in short reaction times. The nanodiatomite@melamine-SO3H was reused five times without substantial activity loss.

Graphical abstract

Nanodiatomite@melamine-SO3H as a novel heterogeneous catalyst was successfully developed and defined through several techniques. The catalyst showed excellent catalytic activity in the xanthene synthesis. The good points of this methodology are ease of product isolation, catalyst efficiency and recycling, cleaner reaction profile, and the procedure agreement with the green chemistry.

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

Scheme 1
Scheme 2
Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6
Figure 7
Figure 8
Scheme 3

Similar content being viewed by others

References

  1. Taran M, Safaei M, Karimi N and Almasi A 2021 Benefits and application of nanotechnology in environmental science: an overview Biointerface Res. Appl. Chem. 11 7860

    CAS  Google Scholar 

  2. Mohamed R M, McKinney D L and Sigmund W M 2012 Enhanced nanocatalysts Mater. Sci. Eng. R. 73 1

    Article  CAS  Google Scholar 

  3. Janićijević J, Krajišnik D, Čalija B, Vasiljević B N and Dobričić V 2015 Modified local diatomite as potential functional drug carrier—A model study for diclofenac sodium Int. J. Pharm. 496 466

    Article  Google Scholar 

  4. Naeimi H and Nazifi Z S 2014 Sulfonated diatomite as heterogeneous acidic nanoporous catalyst for synthesis of 14-aryl-14-H-dibenzo [a, j] xanthenes under green conditions Appl. Catal. A 477 132

    Article  CAS  Google Scholar 

  5. Ghahsare A G, Nazifi Z S and Nazifi S M 2019 Structure-Bioactivity Relationship Study of Xanthene Derivatives: A Brief Review Curr. Org. Synth. 16 1071

    Article  CAS  Google Scholar 

  6. Zukić S and Maran U 2020 Modelling of antiproliferative activity measured in HeLa cervical cancer cells in a series of xanthene derivatives SAR QSAR Environ. Res. 31 905

    Article  Google Scholar 

  7. Reddi Mohan Naidu K, Satheesh Krishna B, Anil Kumar M, Arulselvan P, Ibrahim Khalivulla S 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

    Article  Google Scholar 

  8. Naseem S, Khalid M, Tahir M N, Halim M A and Braga A A 2017 Synthesis, structural, DFT studies, docking and antibacterial activity of a xanthene based hydrazone ligand J. Mol. Struct. 1143 235

    Article  CAS  Google Scholar 

  9. Guo S-H, Leng T-H, Wang K, Wang C-Y, Shen Y-J and Zhu W-H 2018 A colorimetric and turn-on NIR fluorescent probe based on xanthene system for sensitive detection of thiophenol and its application in bioimaging Talanta 185 359

    Article  CAS  Google Scholar 

  10. Shabir G, Saeed A and Ali Channar P 2018 A review on the recent trends in synthetic strategies and applications of xanthene dyes Mini-Rev Org. Chem. 15 166

    Article  CAS  Google Scholar 

  11. Piralghar Z A, Hashemi M M and Ezabadi A 2020 Synthesis and characterization of Brönsted acidic ionic liquid based on ethylamine as an efficient catalyst for the synthesis of xanthene derivatives under solvent-free conditions Polycycl. Aromat. Compd. 40 1510

    Article  Google Scholar 

  12. da Silva M, Forezi L, Marra R K F, de Carvalho da Silva F and Ferreira F V 2017 Synthetic strategies for obtaining xanthenes Curr. Org. Synth. 14 929

    Google Scholar 

  13. Mehravar M, Mirjalili B B F, Babaei E and Bamoniri A 2021 Efficient solvent free synthesis of tetrahydrobenzo [a] xanthene-11-one derivatives using nano-AlPO4/Ti (IV) as a green, heterogeneous and reusable catalyst Inorg. Nano-Metal Chem. 1

  14. Naeimi H and Nazifi Z S 2013 Convenient Synthesis of 14-Aryl-14-H-dibenzo [a, j] xanthenes Catalyzed by Acyclic Brønsted Acidic Ionic Liquid [H—NMP]+[HSO4]− under Microwave Irradiation J. Chin. Chem. Soc. 60 1113

    Article  CAS  Google Scholar 

  15. Darweesh A F, Salama S K, Abdelhamid I A and Elwahy A H 2021 Green synthesis of novel bis (hexahydro-1 H-xanthene-1, 8 (2 H)-diones) employing p-toluenesulfonic acid (p-TSA) as a solid acid catalyst Synth. Commun. 51 471

    Article  CAS  Google Scholar 

  16. Muthukrishnan I, Vachan B, Karuppasamy M, Eniyaval A, Maheswari C U et al 2019 Heterogeneous Amberlyst-15-catalyzed synthesis of complex hybrid heterocycles containing [1, 6]-naphthyridine under metal-free green conditions Org. Bio. Chem. 17 6872

    Article  CAS  Google Scholar 

  17. Alavi S, Mosslemin M H, Mohebat R and Massah A R 2017 Green synthesis of novel quinoxaline sulfonamides with antibacterial activity Res. Chem. Intermed. 43 4549

    Article  CAS  Google Scholar 

  18. Massah A R, Dabagh M, Afshar M, Momeni A R, Aliyan H and Naghash H J 2007 A convenient and efficient synthesis of N-acylsulfonamides in the presence of silica phosphoric acid under heterogeneous and solvent-free conditions Turk. J. Chem. 31 611

    CAS  Google Scholar 

  19. Massah A R, Sayadi S and Ebrahimi S 2012 A green, mild and efficient one-pot method for the synthesis of sulfonamides from thiols and disulfides in water RSC Adv. 2 6606

  20. Abbasi M, Nazifi S M R, Nazifi Z S and Massah A R 2017 Synthesis, characterization and in vitro antibacterial activity of novel phthalazine sulfonamide derivatives J. Chem. Sci. 129 1257

    Article  CAS  Google Scholar 

  21. Massah A R, Kalbasi R J and Samah N 2011 Highly selective synthesis of β-amino carbonyl compounds over ZSM-5-SO 3 H under solvent-free conditions Bull. Korea. Chem. Soc. 32 1703

    Article  CAS  Google Scholar 

  22. Aw M S, Bariana M, Yu Y, Addai-Mensah J and Losic D 2013 Surface-functionalized diatom microcapsules for drug delivery of water-insoluble drugs J. Biomater. Appl. 28 163

    Article  CAS  Google Scholar 

  23. Raeisi-Kheirabadi N, Nezamzadeh-Ejhieh A and Aghaei H 2021 Application of NiOCPE in the quantitative determination of loratadine: Experimental design in square wave voltammetry approach Surf. Interfaces 27 101448

    Article  Google Scholar 

  24. Aghaei H and Ghiaci M 2020 Use of H3PO4/ZrO2–TiO2–surfactant mixed oxide for catalytic vapor-phase dehydration of 1-octanol React. Kinet. Mech. Catal. 131 233

    Article  CAS  Google Scholar 

  25. Aghaei H, Mohammadbagheri Z, Hemasi A and Taghizadeh A 2022 Efficient hydrolysis of starch by α-amylase immobilized on cloisite 30B and modified forms of cloisite 30B by adsorption and covalent methods Food Chem. 373 131425

  26. Aghaei H, Yasinian A and Taghizadeh A 2021 Covalent immobilization of lipase from Candida rugosa on epoxy-activated cloisite 30B as a new heterofunctional carrier and its application in the synthesis of banana flavor and production of biodiesel Int. J. Biol. Macromol. 178 569

    Article  CAS  Google Scholar 

  27. Khozeymeh Nezhad M and Aghaei H 2021 Tosylated cloisite as a new heterofunctional carrier for covalent immobilization of lipase and its utilization for production of biodiesel from waste frying oil Renew. Energ. 164 876

    Article  CAS  Google Scholar 

  28. Zarei A, Khazdooz L, Hajipour A R and Aghaei H 2011 Fast, efficient and convenient method for the preparation of arylazo sulfides using aryl diazonium silica sulfates under mild and solvent-free conditions Dyes Pigm. 91 44

  29. Ghattavi S and Nezamzadeh-Ejhieh A 2020 GC-MASS detection of methyl orange degradation intermediates by AgBr/g-C3N4: Experimental design, bandgap study, and characterization of the catalyst Int. J. Hydrogen Energ. 45 24636

    Article  CAS  Google Scholar 

  30. Bonakdar A P S, Sadeghi A, Aghaei H R, Beheshtimaal K, Nazifi S M R and Massah A R 2020 Convenient Synthesis of Novel Chalcone and Pyrazoline Sulfonamide Derivatives as Potential Antibacterial Agents Russ. J. Bioorg. Chem. 46 371

    Article  CAS  Google Scholar 

  31. Mehrali-Afjani M, Nezamzadeh-Ejhieh A and Aghaei H 2020 A brief study on the kinetic aspect of the photodegradation and mineralization of BiOI-Ag3PO4 towards sodium diclofenac Chem. Phys. Lett. 759 137873

    Article  CAS  Google Scholar 

  32. Raeisi-Kheirabadi N, Nezamzadeh-Ejhieh A and Aghaei H 2021 A brief study on the kinetic of the voltammetric behavior of the modified carbon paste electrode with NiO nanoparticles towards loratadine as a carboxylate-amidic drug compound Microchem. J. 162 105869

  33. Hasheminejad M and Nezamzadeh-Ejhieh A 2015 A novel citrate selective electrode based on surfactant modified nano-clinoptilolite Food Chem. 172 794

    Article  CAS  Google Scholar 

  34. Nezamzadeh-Ejhieh A and Mirzaeyan E 2013 Hexadecylpyridinium surfactant modified zeolite A as an active component of a polymeric membrane sulfite selective electrode Mater. Sci. Eng. C. 33 4751

    Article  CAS  Google Scholar 

  35. Raeisi-Kheirabadi N, Nezamzadeh-Ejhieh A and Aghaei H 2021 Electrochemical amperometric sensing of loratadine using NiO modified paste electrode as an amplified sensor Iran. J. Catal. 11 181

    CAS  Google Scholar 

  36. Karthikeyan G and Pandurangan A 2009 Heteropolyacid (H3PW12O40) supported MCM-41: An efficient solid acid catalyst for the green synthesis of xanthenedione derivatives J. Mol. Catal. A Chem. 311 36

  37. Oskooie H A, Tahershamsi L, Heravi M M and Baghernejad B 2010 Cellulose sulfonic acid: An efficient heterogeneous catalyst for the synthesis of 1, 8-Dioxo-octahydroxanthenes E-J. Chem. 7 717

    Article  CAS  Google Scholar 

  38. Ilangovan A, Malayappasamy S, Muralidharan S and Maruthamuthu S 2011 A highly efficient green synthesis of 1, 8-dioxo-octahydroxanthenes Chem. Cent. J. 5 1

    Article  Google Scholar 

  39. Zare A, Moosavi-Zare A R, Merajoddin M, Zolfigol M A and Hekmat-Zadeh T 2012 Ionic liquid triethylamine-bonded sulfonic acid [Et3N–SO3H] Cl as a novel, highly efficient and homogeneous catalyst for the synthesis of β-acetamido ketones, 1, 8-dioxo-octahydroxanthenes and 14-aryl-14H-dibenzo [a, j] xanthenes J. Mol. Liq. 167 69

    Article  CAS  Google Scholar 

  40. Das B, Thirupathi P, Mahender I, Reddy VS and Rao YK 2006 Amberlyst-15: An efficient reusable heterogeneous catalyst for the synthesis of 1, 8-dioxo-octahydroxanthenes and 1, 8-dioxo-decahydroacridines J. Mol. Catal. A: Chem. 247 233

    Article  CAS  Google Scholar 

  41. Mulakayala N, Kumar G P, Rambabu D, Aeluri M, Rao M B and Pal M 2012 A greener synthesis of 1, 8-dioxo-octahydroxanthene derivatives under ultrasound Tetrahedron Lett. 53 6923

  42. Soliman H A and Salama T A 2013 Silicon-mediated highly efficient synthesis of 1, 8-dioxo-octahydroxanthenes and their transformation to novel functionalized pyrano-tetrazolo [1, 5-a] azepine derivatives Chin. Chem. Lett. 24 404

    Article  CAS  Google Scholar 

  43. Kahandal S S, Burange A S, Kale S R, Prinsen P, Luque R and Jayaram R V 2017 An efficient route to 1, 8-dioxo-octahydroxanthenes and-decahydroacridines using a sulfated zirconia catalyst Catal. Commun. 97 138

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We appreciate the financial support of Shahreza Branch, Islamic Azad University (IAUSH) Research Council.

Author information

Authors and Affiliations

  1. Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran

    ELHAM DAVOODI & ELHAM TAHANPESAR

  2. Department of Chemistry, Khuzestan Science and Research Branch, Islamic Azad University, Ahvaz, Iran

    ELHAM DAVOODI

  3. Department of Chemistry, Shahreza Branch, Islamic Azad University, Shahreza, 86145-311, Isfahan, Iran

    AHMAD REZA MASSAH

Authors
  1. ELHAM DAVOODI
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. ELHAM TAHANPESAR
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. AHMAD REZA MASSAH
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to AHMAD REZA MASSAH.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

DAVOODI, E., TAHANPESAR, E. & MASSAH, A.R. Synthesis of 1,8‐dioxo-octahydroxanthenes utilizing nanodiatomite@melamine-SO3H as a novel heterogeneous catalyst under solvent-free conditions. J Chem Sci 134, 72 (2022). https://doi.org/10.1007/s12039-022-02065-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s12039-022-02065-x

Keywords

Search

Navigation