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Preparation of tin-modified mono-ammonium phosphate fertilizer and its application as heterogeneous catalyst in the benzimidazoles and benzothiazoles synthesis

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Abstract

This work presents an efficient, easy and green method for the benzimidazoles and benzothiazoles synthesis by a condensation reaction of 1,2-diamino benzene and 2-amino thiophenol with various aromatic aldehydes using SnP2O7 as a new heterogeneous catalyst. This catalyst was prepared by adding MAP to the solution of SnCl2 and characterized by microscopic and spectroscopic methods namely X-ray diffraction, scanning electron microscopy and infrared which proved that the chemical structure of MAP has been modified when SnCl2 was added leading to the formation of SnP2O7. On the other hand, the reaction conditions were optimized namely the nature of the solvent and the mass of the catalyst. The high yields (85–97%) and very short reaction times (5–40 min) obtained for various benzimidazoles and benzothiazoles derivatives synthesis show that the new catalyst is very interesting because of its good catalytic activity and its reusability for at least five cycles without any degradation of its activity.

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References

  1. Bahammou I, Esaady A, Boukhris S, Ghailane R, Habbadi N, Hassikou A, Souizi A (2016) Mediterr J Chem 5:615–623

    Article  CAS  Google Scholar 

  2. Sibous S, Boukhris S, Ghailane R, Habbadi N, Hassikou A, Souizi A (2017) J Turk Chem Soc Sect Chem 4:477–488

    CAS  Google Scholar 

  3. Chen G, Liu Z, Zhang Y, Shan X, Jiang L, Zhao Y, He W, Feng Z, Yang S, Liang G (2013) ACS Med Chem Lett 4:69–74

    Article  Google Scholar 

  4. Ibrahim E-SA, Omar A-MME, Khalil MA (1980) J Pharm Sci 69:1348–1350

    Article  CAS  Google Scholar 

  5. Mathew B, Suresh J, Anbazhagan S (2016) J Saudi Chem Soc 20:S132–S139

    Article  CAS  Google Scholar 

  6. Hameed PS, Raichurkar A, Madhavapeddi P, Menasinakai S, Sharma S, Kaur P, Nandishaiah R, Panduga V, Reddy J, Sambandamurthy VK, Sriram D (2014) ACS Med Chem Lett 5:820–825

    Article  Google Scholar 

  7. Fang B, Zhou C-H, Rao X-C (2010) Eur J Med Chem 45:4388–4398

    Article  CAS  Google Scholar 

  8. Shingalapur RV, Hosamani KM, Keri RS, Hugar MH (2010) Eur J Med Chem 45:1753–1759

    Article  CAS  Google Scholar 

  9. MorningstarM L, Roth T, Farnsworth DW, Kroeger Smith M, Watson K, Buckheit RW, Das K, Zhang W, Arnold E, Julias JG, Hughes SH, Michejda CJ (2007) J Med Chem 50:4003–4015

    Article  Google Scholar 

  10. Boiani M, Gonzalez M (2005) Mini-Rev Med Chem 5:409–424

    Article  CAS  Google Scholar 

  11. Zarrinmayeh H, Zimmerman DM, Cantrell BE, Schober DA, Bruns RE, Gackenheimer SL, Ornstein PL, HipskindP A, Britton TC, Gehlert DR (1999) Bioorg Med Chem Lett 9:647–652

    Article  CAS  Google Scholar 

  12. Camacho J, Barazarte A, Gamboa N, Rodrigues J, Rojas R, Vaisberg A, Gilman R, Charris J (2011) Bioorg Med Chem 19:2023–2029

    Article  CAS  Google Scholar 

  13. Heynderickx A, Guglielmetti R, Dubest R, Aubard J, Samat A (2003) Synthesis 2003:1112–1116

    Article  Google Scholar 

  14. Budow S, Kozlowska M, Gorska A, Kazimierczuk Z, Eickmeier H, LaColla P, Gosselin G, Seela F (2009) Arkivoc iii:225–250

    Google Scholar 

  15. Guruswamy B, Arul R (2011) Pharma Chem 3:483–486

    CAS  Google Scholar 

  16. Khan AT, Parvin T, Choudhury LH (2009) Synth Commun 39:2339–2346

    Article  CAS  Google Scholar 

  17. Xiangming H, Huiqiang M, Yulu W (2007) Arkivocx iii:150–154

    Google Scholar 

  18. Gogoi P, Konwar D (2006) Tetrahedron Lett 47:79–82

    Article  CAS  Google Scholar 

  19. Sammaiah B, Sumalatha D, Reddy G, Rajeswari M, Sharada L (2012) Int J Ind Chem 3:11–14

    Article  Google Scholar 

  20. Varala R, Nasreen A, Enugala R, Adapa SR (2007) Tetrahedron Lett 48:69–72

    Article  CAS  Google Scholar 

  21. Shelkar R, Sarode S, Nagarkar J (2013) Tetrahedron Lett 54:6986–6990

    Article  CAS  Google Scholar 

  22. Alinezhad H (2014) Zare M Bulg. Chem Commun 46:347–352

    CAS  Google Scholar 

  23. Singh MP, Sasmal S, Lu W, Chatterjee MN (2000) Synthesis 2000:1380–1390

    Article  Google Scholar 

  24. Trivedi R, De SK, Gibbs RA (2006) J Mol Catal Chem 245:8–11

    Article  CAS  Google Scholar 

  25. Chari MA, Sadanandam P, Shobha D, Mukkanti K (2010) J Heterocycl Chem 47:153–155

    CAS  Google Scholar 

  26. Mukhopadhyay C, Datta A (2009) J Heterocycl Chem 46:91–95

    Article  CAS  Google Scholar 

  27. Benzekri Z, Serrar H, Sibous S, Boukhris S, Ouasri A, Rhandour A, Souizi A (2016) Green Chem Lett Rev 9:223–228

    Article  CAS  Google Scholar 

  28. Zakeri M, Moghadam M, Mirkhani V, Tangestaninejad S, Mohammadpoor-Baltork I, Pahlevanneshan Z (2018) Appl Organomet Chem 32:e3937

    Article  Google Scholar 

  29. Sharghi H, Aberi M, Doroodmand MM, Shiri P (2017) J Iran Chem Soc 14:1557–1573

    Article  CAS  Google Scholar 

  30. Kommula D, Madugula SRM (2017) J Iran Chem Soc 14:1665–1671

    Article  CAS  Google Scholar 

  31. Kumar P, Bhatia R, Khanna R, Dalal A, Kumar D, Surain P, Kamboj RC (2017) J Sulfur Chem 38:585–596

    CAS  Google Scholar 

  32. Goswami M, Dutta MM, Phukan P (2018) Res Chem Intermed 44:1597–1615

    Article  CAS  Google Scholar 

  33. Ye L, Chen J, Mao P, Mao Z, Zhang X, Yan M (2017) Tetrahedron Lett 58:874–876

    Article  CAS  Google Scholar 

  34. Jiang Y, Jia S, Li X, Sun Y, Li W, Zhang W, Xu G (2018) Chem Pap 72:1265–1276

    Article  CAS  Google Scholar 

  35. Jithendra Kumara KS, Krishnamurthy G, Sunil Kumar N, Naik N, Praveen T (2018) J Magn Magn Mater 451:808–821

    Article  CAS  Google Scholar 

  36. Srivastava A, Shukla G, Yadav D, Singh MS (2018) Arkivoc 2:81–89

    Google Scholar 

  37. Feizpour F, Jafarpour M, Rezaeifard A (2018) Catal Lett 148:30–40

    Article  CAS  Google Scholar 

  38. Shojaee S, Mahdavi Shahri M (2018) Appl Organomet Chem 32:e3934

    Article  Google Scholar 

  39. Merroun Y, Chehab S, Ghailane T, Boukhris S, Ghailane R, Habbadi N, Hassikou A, Lakhrissi B, Souizi A (2018) J Turk Chem Soc Sect Chem 5:303–316

    Google Scholar 

  40. Sibous S, Ghailane T, Houda S, Ghailane R, Boukhris S, Souizi A (2017) Mediterr J Chem 6:53–59

    Article  CAS  Google Scholar 

  41. Wang H, Chen J, Qiao R (2014) Ceram Int 40:8465–8468

    Article  CAS  Google Scholar 

  42. Huang M, Huang X, Fei M, Deng Y, Huang X, Xu C, Cheng J, Luo P, Lu Y (2017) Int J Electrochem Sci 12:4585–4596

    Article  CAS  Google Scholar 

  43. Attidekou PS, Connor P, Wormald P, Tunstall D, Francis S, Irvine JTS (2004) Solid State Ion 175:185–190

    Article  CAS  Google Scholar 

  44. Huang C-H, Knop O, Othen DA, Woodhams FWD, Howie RA (1975) Can J Chem 53:79–91

    Article  CAS  Google Scholar 

  45. Safaei-Ghomi J, Teymuri R, Shahbazi-Alavi H, Ziarati A (2013) Chin Chem Lett 24:921–925

    Article  CAS  Google Scholar 

  46. Li L, Zong F, Cui X, Ma H, Wu X, Zhang Q, Wang Y, Yang F, Zhao J (2007) Mater Lett 61:4152–4155

    Article  CAS  Google Scholar 

  47. Uzairu JOA, Gimba CE (2010) J Environ Chem Ecotoxicol 2:126–130

    Google Scholar 

  48. Nandeshwarappa BP, Manjappa S, Kishore B (2011) J Sulfur Chem 32:475–481

    Article  CAS  Google Scholar 

  49. Gover RK, Withers ND, Allen S, Withers RL, Evans JSO (2002) J Solid State Chem 166:42–48

    Article  CAS  Google Scholar 

  50. Fayon F, King IJ, Harris RK, Gover RKB, Evans JSO, Massiot D (2003) Chem Mater 15:2234–2239

    Article  CAS  Google Scholar 

  51. Bezza I, Kaus M, Riekehr L, Pfaffmann L, Doyle S, Indris S, Ehrenberg H, Solhy A, Saadoune I (2016) Phys Chem Chem Phys 18:10375–10382

    Article  CAS  Google Scholar 

  52. Patil MA, Ubale PA, Karhale SS, Helavi VB (2017) Medium Chem Sin 8:198–205

    CAS  Google Scholar 

  53. Teimouri A, Chermahini AN, Salavati H, Ghorbanian L (2013) J Mol Catal Chem 373:38–45

    Article  CAS  Google Scholar 

  54. Sharghi H, Asemani O (2009) Synth Commun 39:860–867

    Article  CAS  Google Scholar 

  55. Mao Z, Wang Z, Li J, Song X, Luo Y (2010) Synth Commun 40:1963–1977

    Article  CAS  Google Scholar 

  56. Shingalapur RV, Hosamani KM (2010) Catal Lett 137:63–68

    Article  CAS  Google Scholar 

  57. Mayo MS, Yu X, Zhou X, Feng X, Yamamoto Y, Bao M (2014) Org Lett 16:764–767

    Article  CAS  Google Scholar 

  58. Martins GM, Puccinelli T, Gariani RA, Xavier FR, Silveira CC, Mendes SR (2017) Tetrahedron Lett 58:1969–1972

    Article  CAS  Google Scholar 

  59. Ziarati A, Sobhani-Nasab A, Rahimi-Nasrabadi M, Ganjali MR, Badiei A (2017) J Rare Earths 35:374–381

    Article  CAS  Google Scholar 

  60. Bardajee GR, Mohammadi M, Yari H, Ghaedi A (2016) Chin Chem Lett 27:265–270

    Article  CAS  Google Scholar 

  61. Riadi Y, Mamouni R, Azzalou R, Haddad ME, Routier S, Guillaumet G, Lazar S (2011) Tetrahedron Lett 52:3492–3495

    Article  CAS  Google Scholar 

  62. Chari MA, Shobha D, Kenawy E-R, Al-Deyab SS, Reddy BVS, Vinu A (2010) Tetrahedron Lett 51:5195–5199

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Laboratory of Organic, Organometallic and Theoretical Chemistry, Faculty of Science, University of IbnTofail, B.P. 133, 14000, Kenitra, Morocco

    Youssef Merroun, Soukaina Chehab, Tourya Ghailane, Abdelaziz Souizi & Rachida Ghailane

  2. Université Sidi Mohammed Ben Abdellah, Cité de l’Innovation, Route d’Immouzer, B.P. 2626, Fez, Morocco

    Mohamed Akhazzane

Authors
  1. Youssef Merroun
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  2. Soukaina Chehab
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  3. Tourya Ghailane
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  4. Mohamed Akhazzane
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  5. Abdelaziz Souizi
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  6. Rachida Ghailane
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Corresponding author

Correspondence to Rachida Ghailane.

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Merroun, Y., Chehab, S., Ghailane, T. et al. Preparation of tin-modified mono-ammonium phosphate fertilizer and its application as heterogeneous catalyst in the benzimidazoles and benzothiazoles synthesis. Reac Kinet Mech Cat 126, 249–264 (2019). https://doi.org/10.1007/s11144-018-1446-5

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