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Silica-Bonded 2-Hydroxyethylammonium Acetate as an Efficient and Recyclable Catalyst for the Synthesis of 2-Amino-4H-chromen-4-yl Phosphonates and β-Phosphonomalonates

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Abstract

Silica-bonded 2-hydroxyethylammonium acetate was synthesized easily by the reaction of 3-chloropropylsilica with ethanolamine followed by ion exchange with acetate. It was used as a heterogeneous, re-usable, efficient and easy to handle catalyst for the one-pot synthesis of a variety of 2-Amino-4H-chromen-4-yl phosphonates and β-phosphonomalonates at room temperature under solvent-free conditions.

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References

  1. Wasserscheid PJ, Keim W (2000) Angew Chem Int Ed 39:3772

    Article  CAS  Google Scholar 

  2. Brown RA, Pollet P, Mckoon E, Eckert CA, Liotta CL, Jessop PG (2001) J Am Chem Soc 123:1254

    Article  CAS  Google Scholar 

  3. Leitner W (2003) Nature 423:930

    Article  CAS  Google Scholar 

  4. Kumar A, Pawar SS (2004) J Org Chem 69:1419

    Article  CAS  Google Scholar 

  5. Welton T (1999) Chem Rev 99:2071

    Article  CAS  Google Scholar 

  6. Zhao D, Liao Y, Zhang Z (2007) Clean 35:42

    Google Scholar 

  7. Kim DW, Chi DY (2004) Angew Chem Int Ed 43:483

    Article  CAS  Google Scholar 

  8. Gadenne B, Hesemann P, Polshettiwar V, Moreau JJE (2006) Eur J Inorg Chem 2006:3697

    Article  Google Scholar 

  9. Desimone RW, Cirrie KS, Mitchell SA, Darrow JW, Pippon DA (2004) Comb Chem High Throughput Screen 7:473

    Article  CAS  Google Scholar 

  10. Bonsignore L, Loy G, Secci D, Calignano A (1993) Eur J Med Chem 28:517

    Article  CAS  Google Scholar 

  11. Patchett AA, Nargund RP (2000) Annu Rep Med Chem 35:289

    Article  CAS  Google Scholar 

  12. Andreani LL, Lapi E (1960) Boll Chim Farm 99:583

    Google Scholar 

  13. Skommer J, Wlodkowic D, Mättö M, Eray M, Pelkonen J (2006) Leukemia Res 30:322

    Article  CAS  Google Scholar 

  14. Wang JL, Liu D, Zhang Z, Shan S, Han X, Srinvasula SM, Croce CM, Alnemeri ES, Huang Z (2000) Proc Natl Acad Sci USA 97:7124

    Article  CAS  Google Scholar 

  15. Elinson MN, Dorofeev AS, Miloserdov FM, Ilovaisky AI, Feducovich SK, Belyakov PA, Nikishin GI (2008) Adv Synth Catal 350:591

    Article  CAS  Google Scholar 

  16. Moafi L, Ahadi S, Bazgir A (2010) Tetrahedron Lett 51:6270

    Article  CAS  Google Scholar 

  17. Rajasekhar M, Rao KUM, Sundar CS, Reddy NB, Nayak SK, Reddy CS (2012) Chem Pharm Bull 60:854

    CAS  Google Scholar 

  18. Jayashree P, Shanthi G, Perumal PT (2009) Synlett 6:917

    Google Scholar 

  19. Narayana Murthy S, Madhav B, Prakash Reddy V, Nageswar YVD (2010) Tetrahedron Lett 51:3649

    Article  Google Scholar 

  20. Gaikwad DS, Undale KA, Shaikh TS, Pore DM (2011) C R Chimie 14:865

    Article  CAS  Google Scholar 

  21. Kulkarni MA, Pandurangi VR, Desai UV, Wadgaonkar PP (2012) C R Chimie 15:745

    Article  CAS  Google Scholar 

  22. Das B, Balasubramanyam P, Reddy GC, Nayaki S (2011) Helv Chim Acta 94:1347

    Article  CAS  Google Scholar 

  23. Kolla SR, Lee YR (2012) Tetrahedron 68:226

    Article  CAS  Google Scholar 

  24. Sobhani S, Safaei E, Asadi M, Jalili F, Tashrifi Z (2008) J Porphyrins Phthalocyanines 12:849

    Article  CAS  Google Scholar 

  25. Sobhani S, Rezazadeh S (2011) J Iran Chem Soc 8:198

    Article  CAS  Google Scholar 

  26. Sobhani S, Tashrifi Z (2009) Heteroatom Chem 20:109

    Article  CAS  Google Scholar 

  27. Sobhani S, Tashrifi Z (2009) Synth Commun 39:120

    Article  CAS  Google Scholar 

  28. Sobhani S, Rezazadeh S (2010) Synlett 2010:1485

    Article  Google Scholar 

  29. Sobhani S, Vafaee A (2009) Tetrahedron 65:7691

    Article  CAS  Google Scholar 

  30. Sobhani S, Pakdin Parizi Z, Razavi N (2011) Appl Catal A 162:409–410

    Google Scholar 

  31. Sobhani S, Pakdin Parizi Z, Rezazadeh S (2011) J Organomet Chem 696:813

    Article  CAS  Google Scholar 

  32. Sobhani S, Safaei E, Asadi M, Jalili F (2008) J Organomet Chem 693:3313

    Article  CAS  Google Scholar 

  33. Sobhani S, Pakdin Parizi Z (2011) Tetrahedron 67:3540

    Article  CAS  Google Scholar 

  34. Sobhani S, Honarmand M (2012) J Iran Chem Soc 9:661

    Article  CAS  Google Scholar 

  35. Sobhani S, Honarmand M (2013) Synlett 24:236

    Google Scholar 

  36. Bi W, Zhou J, Row KH (2010) Anal Chim Acta 677:162

    Article  CAS  Google Scholar 

  37. Sobhani S, Honarmand M (2013) C R Chim. doi:10.1016/j.crci.2012.10.011

  38. Sobhani S, Nasseri R, Honarmand M (2012) Can J Chem 90:1

    Article  Google Scholar 

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Acknowledgments

We are thankful to University of Birjand Research Council for their support on this work.

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Authors and Affiliations

  1. Department of Chemistry, College of Sciences, University of Birjand, Birjand, 414, Iran

    Sara Sobhani & Moones Honarmand

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  1. Sara Sobhani
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  2. Moones Honarmand
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Correspondence to Sara Sobhani.

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Sobhani, S., Honarmand, M. Silica-Bonded 2-Hydroxyethylammonium Acetate as an Efficient and Recyclable Catalyst for the Synthesis of 2-Amino-4H-chromen-4-yl Phosphonates and β-Phosphonomalonates. Catal Lett 143, 476–485 (2013). https://doi.org/10.1007/s10562-013-0968-8

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  • DOI: https://doi.org/10.1007/s10562-013-0968-8

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