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A green eco approach toward the synthesis of novel 4-iminoquinoline derivatives using Brønsted acid nanocatalysts

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Abstract

A series of novel 4-iminoquinolines were synthesized from the reaction of 2-aminobenzonitrile, orthoesters, and active methylenes in the presence of Brønsted acid nanocatalysts (Fe3O4@APTES-MAH NPs or VSA NRs) under solvent-free conditions. VSA NRs were prepared by the reaction of the chlorosulfonic acid and sodium monovanadate at high purity. The amine-surfaced Fe3O4@APTES NPs prepared using the coating of Fe3O4 nanoparticles with 3-aminopropyltriethoxysilane were further modified with maleic anhydride to produce Fe3O4@APTES-MAH NPs. The reaction is characterized by high yields, simple purification of the products, inexpensive, short reaction times, reusability, and stability of the catalysts.

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References

  1. Benard C, Zouhiri F, Normand-Bayle M, Danet M, Desmaele D, Leh H, Mouscadet JF, Mbemba G, Thomas CM, Bonnenfant S, Le Bret M, d’Angelo J (2004) Bioorg Med Chem Lett 14:2473

    Article  CAS  Google Scholar 

  2. Kumar A, Paliwal D, Saini D, Thakur A, Aggarwal S, Kaushik D (2014) Eur J Med Chem 85:147

    Article  CAS  Google Scholar 

  3. Solomon VR, Lee H (2011) Curr Med Chem 18:1488

    Article  CAS  Google Scholar 

  4. Rossiter S, Péron JM, Whitfield PJ, Jones K (2005) Bioorg Med Chem Lett 15:4806

    Article  CAS  Google Scholar 

  5. Sanjay RP, Rahul G, Sangamwar AT (2015) Eur J Med Chem 93:511

    Article  Google Scholar 

  6. Inam A, Siddiqui SM, Macedo TS, Moreira DRM, Leite ACL, Soares MBP, Azam A (2014) Eur J Med Chem 75:67

    Article  CAS  Google Scholar 

  7. Xia LK, Idhayadhulla A, Lee YR, Kim SH, Wee Y (2014) J Comb Sci 16:333

    Article  CAS  Google Scholar 

  8. Pramanik A, Bhar S (2012) Catal Commun 20:17

    Article  CAS  Google Scholar 

  9. Eswaran S, Adhikari AV, Chowdhury IH, Pal NK, Thomas KD (2010) Eur J Med Chem 45:3374

    Article  CAS  Google Scholar 

  10. Jenekhe SA, Lu L, Alam MM (2001) Macromolecules 34:7315

    Article  CAS  Google Scholar 

  11. Skraup H (1880) Chem Ber 13:2086

    Google Scholar 

  12. Combes A (1888) Bull Chim Soc Fr 49:89

    Google Scholar 

  13. Friedlander P (1882) Chem Ber 15:2572

    Article  Google Scholar 

  14. Pfitzinger W (1886) J Prakt Chem 33:100

    Article  Google Scholar 

  15. Doebner O, von Miller W (1881) Chem Ber 14:2812

    Article  Google Scholar 

  16. Van Es T, Staskun BS (2002) Afr J Chem 55:13

    Google Scholar 

  17. Ghorab MM, Ragab FA, Hamed MM (2009) Eur J Med Chem 44:4211

    Article  CAS  Google Scholar 

  18. Sun XW, Liu M, Xu MH, Lin GQ (2008) Org Lett 10:1259

    Article  CAS  Google Scholar 

  19. Corey EJ, Grogan MJ (1999) Org Lett 1:157

    Article  CAS  Google Scholar 

  20. Iravani N, Keshavarz M, Mousavi M, Baghernejad M (2015) Iran J Catal 5:169

    Google Scholar 

  21. Nasr-Esfahani M, Daghaghale M, Taei M (2016) J Chin Chem Soc 64:17

    Article  Google Scholar 

  22. Wilson K, Adams DJ, Rothenberg G, Clark JH (2000) J Mol Catal A Chem 159:309

    Article  CAS  Google Scholar 

  23. Kiss AA, Dimian AC, Rothenberg G (2006) Adv Synth Catal 348:75

    Article  CAS  Google Scholar 

  24. Qiu G, Wang Q, Wang C, Lau W, Guo Y (2007) Ultrason Sonochem 14:55

    Article  CAS  Google Scholar 

  25. Ye Y, Pan Z, Zhang L, He L, Xia A, Liang H (2010) J Polym Sci B Polym Phys 48:1873

    Article  CAS  Google Scholar 

  26. Wu W, He Q, Jiang Ch (2008) Nanoscale Res Lett 3:397

    Article  CAS  Google Scholar 

  27. Nasr-Esfahani M, Hoseini SJ, Montazerozohori M, Mehrabi R, Nasrabadi H (2014) J Mol Catal A Chem 382:99

    Article  CAS  Google Scholar 

  28. Ghasemzadeh MA, Safaei-Ghomi J, Molaei H (2012) C R Chim 15:969

    Article  CAS  Google Scholar 

  29. Karami B, Hoseini SJ, Nikoseresht S, Khodabakhshi S (2012) Chin Chem Lett 23:173

    Article  CAS  Google Scholar 

  30. Ghasemzadeh MA, Safaei-Ghomi J, Zahedi S (2013) J Serbian Chem Soc 78:769

    Article  CAS  Google Scholar 

  31. Martinez R, Ramon DJ, Yus M (2008) Adv Synth Catal 350:1235

    Article  CAS  Google Scholar 

  32. Nasr-Esfahani M, Rafiee Z, Montazerozohori M, Kashi H (2016) RSC Adv 6:47298

    Article  CAS  Google Scholar 

  33. Petez JM, Simeone FJ, Saski Y, Josephson L, Weissleder R (2003) J Am Chem Soc 125:10192

    Article  Google Scholar 

  34. Ling Y, Wei K, Luo Y, Gao X, Zhong S (2011) Biomaterials 32:7139

    Article  CAS  Google Scholar 

  35. Purushotham S, Ramanujan RV (2010) Acta Biomater 6:502

    Article  CAS  Google Scholar 

  36. Mashhadizadeh MH, Amoli-Diva M, Shapouri MR, Afruzi H (2014) Food Chem 151:300

    Article  CAS  Google Scholar 

  37. Rafiee E, Paknezhad F, Shahebrahimi Sh, Joshaghani M, Eavani S, Rashidzadeh S (2008) J Mol Catal A Chem 282:92

    Article  CAS  Google Scholar 

  38. Elison MN, Dorofeev A, Nasybullin RF, Feducovich SK, Nikishin GI (2008) Electrochim Acta 53:5022

    Article  Google Scholar 

  39. Safaei-Ghomi J, Fadaeian M, Hatami A (2007) Turk J Chem 31:89

    CAS  Google Scholar 

  40. Nasr-Esfahani M, Abdizadeh T (2013) J Nanosci Nanotechnol 13:5004

    Article  CAS  Google Scholar 

  41. Nasr-Esfahani M, Abdizadeh T (2013) Rev Roum Chim 58:27

    CAS  Google Scholar 

  42. Nasr-Esfahani M, Abdizadeh T (2013) Phosphorus Sulfur 188:596

    Article  CAS  Google Scholar 

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Acknowledgements

We are grateful to the Yasouj University for supporting this work.

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Correspondence to Masoud Nasr-Esfahani.

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Kanaani, E., Nasr-Esfahani, M. A green eco approach toward the synthesis of novel 4-iminoquinoline derivatives using Brønsted acid nanocatalysts. Monatsh Chem 149, 543–550 (2018). https://doi.org/10.1007/s00706-017-2069-7

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  • DOI: https://doi.org/10.1007/s00706-017-2069-7

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