Skip to main content
SpringerLink
Log in

Molybdenum anchored onto zeolite beta: an efficient catalyst for the one-pot synthesis of octahydroquinazolinone derivatives under solvent-free conditions

  • Published:
Reaction Kinetics, Mechanisms and Catalysis Aims and scope Submit manuscript

Abstract

In the present work, the heterogenization of MoO2(acac)2 onto imine functionalized zeolite beta is reported. The catalyst was characterized by Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), scanning electron microscopy-energy dispersive X-ray analysis (SEM–EDX), BET surface area measurements, CHN microanalysis and inductively coupled plasma (ICP). The activity of the catalyst was assessed in the synthesis of octahydroquinazolinone derivatives under reflux condition and microwave irradiation. The catalyst can be recycled and reused five times without significant loss of activity.

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
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Scheme 3
Fig. 5

Similar content being viewed by others

References

  1. Domling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106:17–89

    Article  CAS  PubMed  Google Scholar 

  2. Arndtsen BA (2009) Metal-catalyzed one-step synthesis: towards direct alternatives to multistep heterocycle and amino acid derivative formation. Chem Eur J 15:302–313

    Article  CAS  PubMed  Google Scholar 

  3. Kappe CO (2000) Biologically active dihydropyrimidones of the Biginelli-type: a literature survey. Eur J Med Chem 35:1043–1052

    Article  CAS  PubMed  Google Scholar 

  4. Ashok M, Holla BS, Kumari NS (2007) Convenient one pot synthesis of some novel derivatives of thiazolo[2,3-b]dihydropyrimidinone possessing 4-methylthiophenyl moiety and evaluation of their antibacterial and antifungal activities. Eur J Med Chem 42:380–385

    Article  CAS  PubMed  Google Scholar 

  5. Kwon OW, Moon E, Chari MA, Kim TW, Kim AJ, Lee P, Ahn KH, Kim SY (2012) A substituted 3,4-dihydropyrimidinone derivative (compound D22) prevents inflammation mediated neurotoxicity; role in microglial activation in BV-2 cells. Bioorg Med Chem Lett 22:5199–5203

    Article  CAS  PubMed  Google Scholar 

  6. Kidwai M, Saxena S, Khan MKR, Thukral SS (2005) Synthesis of 4-aryl-7,7-dimethyl-1,2,3,4,5,6,7,8 octahydroquinazoline-2-one/thione-5-one derivatives and evaluation as antibacterials. Eur J Med Chem 40:816–819

    Article  CAS  PubMed  Google Scholar 

  7. Yarim M, Sarac S, Kilic FS, Erol K (2003) Synthesis and in vitro calcium antagonist activity of 4-aryl-7,7-dimethyl/1,7,7-trimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione derivatives. IlFarmaco 58:17–24

    Article  CAS  Google Scholar 

  8. Ladani NK, Patel MP, Patel RG (2009) An efficient three component one-pot synthesis of some new octahydroquinazolinone derivatives and investigation of their antimicrobial activities. ARKIVOC 7:292–302

    Google Scholar 

  9. Hassani Z, Islami MR, Kalantari M (2006) An efficient one-pot synthesis of octahydroquinazolinone derivatives using catalytic amount of H2SO4 in water. Bioorg Med Chem Lett 16:4479–4482

    Article  CAS  PubMed  Google Scholar 

  10. Kantevari S, Bantu R, Nagarapu L (2006) TMSCl mediated highly efficient one-pot synthesis of octahydroquinazolinone and 1,8-dioxo-octahydroxanthene derivatives. ARKIVOC 16:136–148

    Google Scholar 

  11. Lin H, Zhao Q, Xu B, Wang X (2007) Nafion-H catalyzed cyclocondensation reaction for the synthesis of octahydroquinazolinone derivatives. J Mol Catal A 268:221–226

    Article  CAS  Google Scholar 

  12. Khurana JM, Kumar S (2010) Ionic liquid: an efficient and recyclable medium for the synthesis of octahydroquinazolinone and biscoumarin derivatives. Monatsh Chem 141:561–564

    Article  CAS  Google Scholar 

  13. Mobinikhaledi A, Foroughifar N, Khodaei H (2010) Synthesis of octahydroquinazolinone derivatives using silica sulfuric acid as an efficient catalyst. Eur J Chem 1:291–293

    Article  CAS  Google Scholar 

  14. Azzam SHS, Siddekha A, Nizam A, Pasha MA (2012) SiO2-NaHSO4 as an efficient reusable heterogeneous catalyst for the one-pot three-component synthesis of octahydro-quinazolin-2,5-diones in water. Chin J Catal 33:677–680

    Article  CAS  Google Scholar 

  15. Heravi MM, Karimi N, Hamidi H, Oskooie HA (2013) Cu/SiO2:a recyclable catalyst for the synthesis of octahydroquinazolinone. Chin Chem Lett 24:143–144

    Article  CAS  Google Scholar 

  16. Lidstrom P, Tierney J, Wathey B, Westman J (2001) Microwave assisted organic synthesis: a review. Tetrahedron 57:9225–9283

    Article  CAS  Google Scholar 

  17. Kappe CO, Stadler A (2005) Microwaves in organic and medicinal chemistry. Wiley, Weinheim

    Book  Google Scholar 

  18. Loupy A (2002) Microwaves in organic synthesis. Wiley, Weinheim

    Book  Google Scholar 

  19. Ranu BC, Hajra A, Jana U (2000) Microwave assisted simple synthesis of quinolones from anilines and alkyl vinyl ketones on the surface of silica gel in the presence of indium(III)chloride. Tetrahedron Lett 41:531–533

    Article  CAS  Google Scholar 

  20. Quiroga J, Cisneros C, Insuasty B, Abonia R, Nogueras M, Sanchez A (2001) A regiospecific three-component one-step cyclocondensation to 6-cyano-5,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-ones using microwaves under solvent-free conditions. Tetrahedron Lett 42:5625–5627

    Article  CAS  Google Scholar 

  21. Niralwad KS, Shingate BB, Shingare MS (2010) Microwave-assisted one-pot synthesis of octahydroquinazolinone derivatives using ammonium metavanadate under solvent-free condition. Tetrahedron Lett 51:3616–3618

    Article  CAS  Google Scholar 

  22. Badadhe PV, Chate AV, Hingane DG, Mahajan PS, Chavhan NM, Gill CH (2011) Microwave-assisted one-pot synthesis of octahydroquinazolinone derivatives catalyzed by thiamine hydrochloride under solvent-free condition. J Korean Chem Soc 55:936–939

    Article  CAS  Google Scholar 

  23. Samantaray S, Mishra BG (2011) Combustion synthesis, characterization and catalytic application of MoO3–ZrO2 nanocomposite oxide towards one pot synthesis of octahydroquinazolinonesJ. Mol Catal A Chem 339:92–98

    Article  CAS  Google Scholar 

  24. Jadhav S, Anandgaonker PL, Kulkarni G, Gaikwad ST, Rajbhoj AS (2014) Microwave-assisted one-pot synthesis of octahydroquinazolinone derivatives using molybdenum oxide nanoparticles in solvent-free condition. J Clust Sci 25:1389–1399

    Article  CAS  Google Scholar 

  25. Kuraitheerthakumaran A, Pazhamalai S, Manikandan H, Gopalakrishnan M (2014) J Saudi Chem Soc 18:920–924

    Article  Google Scholar 

  26. Arnold U, Cruz RSD, Mandelli D, Schuchardt U (2001) Activity, selectivity and stability of metallosilicates containing molybdenum for the epoxidation of alkenes. J Mol Catal A 165:149–158

    Article  CAS  Google Scholar 

  27. Fuerte A, Iglesias M, Sanchez F, Corma A (2004) Chiral dioxomolybdenum(VI) and oxovanadium(V) complexes anchored on modified USY-zeolite and mesoporous MCM-41 as solid selective catalysts for oxidation of sulfides to sulfoxides or sulfones. J Mol Catal A 211:227–235

    Article  CAS  Google Scholar 

  28. Reyes P, Borda G, Gnecco J, Rivas BL (2004) MoO2(acac)2 immobilized on polymers as catalysts for cyclohexene epoxidation: effect of the degree of crosslinking. J Appl Polym Sci 93:1602–1608

    Article  CAS  Google Scholar 

  29. Wang G, Feng L, Luck RL, Evans DG, Wang Z, Duan X (2005) Sol-gel synthesis, characterization and catalytic property of silicas modified with oxomolybdenum complexes. J Mol Catal A 241:8–14

    Article  CAS  Google Scholar 

  30. Sakthivel A, Zhao J, Raudaschl-Sieber G, Hanzlik M, Chiang AST, Kuhn FE (2005) Heterogenization of chiral molybdenum(VI)dioxo complexes on mesoporous materials and their application in catalysis. Appl Catal A 281:267–273

    Article  CAS  Google Scholar 

  31. Bruno SM, Fernandes JA, Martins LS, Goncalves IS, Pillinger M, Ribeiro-Claro P, Rocha J, Valente AA (2006) Dioxomolybdenum(VI) modified mesoporous materials for the catalytic epoxidation of olefins. Catal Today 114:263–271

    Article  CAS  Google Scholar 

  32. Masteri-Farahani M, Farzaneh F, Ghandi M (2006) Synthesis and characterization of molybdenum complexes with bidentate Schiff base ligands within nanoreactors of MCM-41 as epoxidation catalysts. J Mol Catal A 248:53–60

    Article  CAS  Google Scholar 

  33. Bakala PC, Briot E, Salles L, Bregeault JM (2006) Comparison of liquid-phase olefin epoxidation over MoOx inserted within mesoporous silica (MCM-41, SBA-15) and grafted onto silica. Appl Catal A 300:91–99

    Article  CAS  Google Scholar 

  34. Tangestaninejad S, Moghadam M, Mirkhani V, Mohammadpoor-Baltork I, Ghani K (2008) MoO2(acac)2 supported on silica functionalized imidazole as a highly efficient and reusable catalyst for alkene epoxidation with tert-BuOOH. Inorg Chem Commun 11:270–274

    Article  CAS  Google Scholar 

  35. Gomes AC, Bruno SM, Gago S, Lopes RP, Machado DA, Carminatti AP, Valente AA, Pillinger M, Goncalves IS (2011) Epoxidation of cyclooctene using soluble or MCM-41-supported molybdenum tetracarbonylepyridylimine complexes as catalyst precursors. J Organomet Chem 696:3543–3550

    Article  CAS  Google Scholar 

  36. Farias M, Martinelli M, Rolim GK (2011) Immobilized molybdenum acetylacetonate complex on montmorillonite K-10 as catalyst for epoxidation of vegetable oils. Appl Catal A 403:119–127

    Article  CAS  Google Scholar 

  37. Sharma RK, Pandey A, Gulati S (2012) Silica-supported molybdenum complex: a novel, selective and reusable organic–inorganic hybrid catalyst for eco-friendly oxidation of sulfides and olefins. Polyhedron 45:86–93

    Article  CAS  Google Scholar 

  38. Esnaashari F, Moghadam M, Mirkhani V, Tangestaninejad S, MohammadpoorBaltork I, Khosoropour AR, Zakeri M, Hushmandrad S (2012) MoO2(acac)2 supported on multi-wall carbon nanotubes: highly efficient and reusable catalysts for alkene epoxidation with tert-BuOOH. Polyhedron 48:212–220

    Article  CAS  Google Scholar 

  39. Gao B, Wan M, Men J, Zhang Y (2012) Aerobic selective oxidation of benzyl alcohols to benzaldehyde catalyzed by bidentate Schiff base dioxomolybdenum(VI) complex immobilized on CPS microspheres. Appl Catal A 439–440:156–162

    Article  CAS  Google Scholar 

  40. Esnaashari F, Moghadam M, Mirkhani V, Tangestaninejad S, Mohammadpoor-Baltork I, Khosoropour AR, Zakeri M (2012) Multi-wall carbon nanotubes supported molybdenyl acetylacetonate: efficient and highly reusable catalysts for epoxidation of alkenes with tert-butyl hydroperoxide. Mater Chem Phys 137:69–75

    Article  CAS  Google Scholar 

  41. Rayati S, Abdolalian P (2013) Heterogenization of a molybdenum Schiff base complex as a magnetic nanocatalyst: an eco-friendly, efficient, selective and recyclable nanocatalyst for the oxidation of alkenes. C R Chim 16:814–820

    Article  CAS  Google Scholar 

  42. Zhang J, Jiang P, Shen Y, Zhang W, Li X (2015) Molybdenum(VI) complex with a tridentate Schiff base ligand immobilized on SBA-15 as effective catalysts in epoxidation of alkenes. Microporous Mesoporous Mater 206:161–169

    Article  CAS  Google Scholar 

  43. Tabatabaeian K, Zanjanchi MA, Mamaghani M, Dadashi A (2014) Anchoring of ruthenium onto imine functionalized zeolitebeta: an efficient route for the synthesis of 4H-benzo[b]pyrans and pyrano[c]chromenes. Can J Chem 92:1086–1091

    Article  CAS  Google Scholar 

  44. Robson H (2001) Verified synthesis of zeolitic materials, 2nd edn. Elsevier, Amesterdam

    Google Scholar 

  45. Ortiz-Iniesta MJ, Heeres HJ, Melian-Cabrera I (2013) Direct activation of microcrystalline zeolites. Microporous Mesoporous Mater 171:208–214

    Article  CAS  Google Scholar 

  46. Liu H, Wang L, Li P (2008) Highly efficient and recyclable palladium catalyst anchored on organic-inorganic hybrid material: application in the heck reaction. Synthesis 38:2405–2411

    Google Scholar 

  47. Sharma RK, Rawat D (2012) Silica immobilized nickel complex: an efficient and reusable catalyst for microwave-assisted one-pot synthesis of dihydropyrimidinones. Inorg Chem Commun 17:58–63

    Article  CAS  Google Scholar 

Download references

Acknowledgement

We are grateful to the Research Council of University of Guilan for their partial support.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, University of Guilan, Rasht, P.O. Box 41635-1914, Islamic Republic of Iran

    Ali Dadashi Hadigavabar, Khalil Tabatabaeian, Mohammad Ali Zanjanchi & Manouchehr Mamaghani

Authors
  1. Ali Dadashi Hadigavabar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Khalil Tabatabaeian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mohammad Ali Zanjanchi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Manouchehr Mamaghani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ali Dadashi Hadigavabar.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hadigavabar, A.D., Tabatabaeian, K., Zanjanchi, M.A. et al. Molybdenum anchored onto zeolite beta: an efficient catalyst for the one-pot synthesis of octahydroquinazolinone derivatives under solvent-free conditions. Reac Kinet Mech Cat 124, 857–871 (2018). https://doi.org/10.1007/s11144-018-1370-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11144-018-1370-8

Keywords

Search

Navigation