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An iron Schiff base complex loaded mesoporous silica nanoreactor as a catalyst for the synthesis of pyrazine-based heterocycles

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Abstract

An iron Schiff base complex was encapsulated in SBA-15 mesoporous silica to afford a Fe(III)-Schiff base/SBA-15 heterogeneous nanocatalyst for the synthesis of pyridopyrazine and quinoxaline heterocycles. These reactions proceeded in water with excellent yields. The catalyst was characterized by physico-chemical and spectroscopic methods and found to retain the characteristic channel structures of the SBA-15, allowing good accessibility of the encapsulated metal complex.

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References

  1. Corma A (1997) Chem Rev 97:2373–2420

    Article  CAS  Google Scholar 

  2. Asefa T, MacLachlan MJ, Coombs N, Ozin GA (1999) Nature 402:867–871

    CAS  Google Scholar 

  3. Gupta KC, Sutar AK (2008) Coord Chem Rev 252:1420–1450

    Article  CAS  Google Scholar 

  4. Li C (2004) Cat Rev Sci Eng 46:419–492

    Article  CAS  Google Scholar 

  5. Karimi B, Zamani A, Clark JH (2005) Organometalics 24:4695–4698

    Article  CAS  Google Scholar 

  6. Yadav JS, Reddy BVS, Premalatha K, Shankar KS (2008) Synthesis 23:3787–3792

    Article  Google Scholar 

  7. He W, Meyers MR, Hanney B, Sapada A, Blider G, Galzeinski H, Amin D, Needle S, Page K, Jayyosi Z, Perrone H (2003) Bioorg Med Chem Lett 13:3097–3100

    Article  CAS  Google Scholar 

  8. Huang TK, Wang R, Shi L, Lu XX (2008) Catal Commun 9:1143–1147

    Article  CAS  Google Scholar 

  9. Cho CS, Renb WX, Shim SC (2007) Tetrahedron Lett 48:4665–4667

    Article  CAS  Google Scholar 

  10. Das B, Lu KV, Suneel K, Majhi A (2007) Tetrahedron Lett 48:5371–5374

    Article  CAS  Google Scholar 

  11. Cohen Y, Meyer AY, Rabinovitz M (1986) J Am Chem Soc 108:7039–7044

    Article  CAS  Google Scholar 

  12. Goswami S, Adak AK (2005) Tetrahedron Lett 46:221–224

    Article  CAS  Google Scholar 

  13. Cho CS, Oh SG (2007) J Mol Catal A Chem 276:205–210

    Article  CAS  Google Scholar 

  14. Takekuma SI, Katayama S, Takekuma H (2000) Chem Lett 6:614–615

    Article  Google Scholar 

  15. Chisem IC, Rafelt J, Shieh MT, Chisem J, Clark JH, Jachuck R, Macquarrie D, Ramshaw C, Scott K (1998) Chem Commun 18:1949–1950

    Article  Google Scholar 

  16. Zhao D, Feng J, Huo Q, Melosh N, Fredrickson GH, Chmelka B, Stucky GD (1998) Science 279:548–552

    Article  CAS  Google Scholar 

  17. Hou JT, Liu YH, Zhang ZH (2010) J Heterocycl Chem 47:703–706

    CAS  Google Scholar 

  18. Li J, Jiang DN, Chen JX, Liu MC, Ding JC, Wu HY (2011) J Heterocycl Chem 48:403–406

    Article  CAS  Google Scholar 

  19. Naskar JP, Chowdhury S, Drew MGB, Datta D (2002) New J Chem 26:170–175

    Article  CAS  Google Scholar 

  20. Aghapoor K, Darabi HR, Mohsenzadeh F, Balavar Y, Daneshyar H (2010) Transit Met Chem 35:49–53

    Article  CAS  Google Scholar 

  21. Alinezhad H, Tajbakhsh M, Salehian F, Biparva P (2011) Bull Korean Chem Soc 32:3720–3726

    Article  CAS  Google Scholar 

  22. Lü HY, Yang SH, Deng J, Zhang ZH (2010) Aust J Chem 63:1290–1296

    Article  Google Scholar 

  23. Antoine M, Czech M, Gerlach M, Günther E, Schuster T, Marchand P (2011) Synthesis 5:794–806

    Google Scholar 

  24. Appel R, Volz P (1975) Chem Ber 108:623–628

    Article  CAS  Google Scholar 

  25. Mohammadi K, Hasaninejad A, Niad M, Najmi M (2010) J Porphyr Phthalocya 14:1052–1058

    Article  CAS  Google Scholar 

  26. Rothkopf HW, Weohrle D, Meuller R, Kossmehl G (1975) Chem Ber 108:875–882

    Article  CAS  Google Scholar 

  27. Masteri Farahani M, Farzaneh F, Ghandi M (2006) J Mol Catal A Chem 248:53–60

    Article  CAS  Google Scholar 

  28. Limand MH, Stein A (1999) Chem Mater 11:3285–3295

    Article  Google Scholar 

  29. Zhang WH, Lu XB, Xiu JH, Hua ZL, Zhang LX, Robertson M, Shi JL, Yan DS, Holmes JD (2004) Adv Funct Mater 14:544–552

    Article  CAS  Google Scholar 

  30. Jana S, Dutta B, Bera R, Koner S (2007) Langmuir 23:2492–2496

    Article  CAS  Google Scholar 

  31. Singh UG, Williams RT, Hallam KR, Allen GC (2005) J Solid State Chem 178:3405–3413

    Article  CAS  Google Scholar 

  32. Singha S, Parida KM, Dash AC (2011) J Porous Mater 18:707–714

    Article  CAS  Google Scholar 

  33. Anand N, Reddy KHP, Rao KSR, Burri DR (2011) Catal Lett 141:1355–1363

    Article  CAS  Google Scholar 

  34. Karimi B, Zamani A, Abedia S, Clark JH (2009) Green Chem 11:109–119

    Article  CAS  Google Scholar 

  35. Subrahmanyam CS, Narayanan S (2011) Asian J Chem 23:1331–1333

    CAS  Google Scholar 

  36. Venkateswarlu Y, Leelavathi P (2010) Lett Org Chem 7:208–211

    Article  CAS  Google Scholar 

  37. Narsaiah AV, Kumar JK (2012) Synth Commun 42:883–892

    Article  CAS  Google Scholar 

  38. Raghuveerachary P, Devanna N (2011) Asian J Chem 23:1628–1630

    CAS  Google Scholar 

  39. Bardajee GR, Malakooti R, Jami F, Parsaei Z, Parsaei Z, Atashin H (2012) Catal Commun 27:49–53

    Article  CAS  Google Scholar 

  40. Bardajee GR, Malakooti R, Abtin I, Atashin H (2013) Micropor Mesopor Mater 169:67–74

    Article  CAS  Google Scholar 

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Acknowledgments

Authors are thankful to University of Birjand and Pyame Noor University for financial support of this study.

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Authors and Affiliations

  1. Nanochemistry Research Laboratory, Department of Chemistry, University of Birjand, PO Box 97175-615, Birjand, Iran

    Reihaneh Malakooti, Somayyeh Hadizadeh & Hassan Atashin

  2. Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran

    Ghasem Rezanejade Bardajee & Hadiseh Khanjari

Authors
  1. Reihaneh Malakooti
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  2. Ghasem Rezanejade Bardajee
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  3. Somayyeh Hadizadeh
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  4. Hassan Atashin
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  5. Hadiseh Khanjari
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Corresponding authors

Correspondence to Reihaneh Malakooti or Ghasem Rezanejade Bardajee.

Electronic supplementary material

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11243_2013_9772_MOESM1_ESM.docx

Supplementary material 1 TGA analysis and IR spectra of the support and catalyst in addition to 1H and 13C NMR spectra for some products. (DOCX 9624 kb)

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Malakooti, R., Bardajee, G.R., Hadizadeh, S. et al. An iron Schiff base complex loaded mesoporous silica nanoreactor as a catalyst for the synthesis of pyrazine-based heterocycles. Transition Met Chem 39, 47–54 (2014). https://doi.org/10.1007/s11243-013-9772-y

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  • DOI: https://doi.org/10.1007/s11243-013-9772-y

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