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P2O5–SiO2 as an efficient heterogeneous catalyst for the solvent-free synthesis of 1-substituted 1H-1,2,3,4-tetrazoles under conventional and ultrasound irradiation conditions

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Abstract

1-Substituted 1H-1,2,3,4-tetrazoles were efficiently synthesized from the reaction of primary amines, triethyl orthoformate, and sodium azide in presence of a catalytic amount of P2O5–SiO2 under conventional and ultrasound irradiation in solvent-free conditions. The advantages of this procedure are high yields, relatively short reaction times, ease of product isolation, low cost, and recovery and reusability of the catalyst.

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References

  1. Herr RJ (2002) Bioorg Med Chem 10:3379

    Article  CAS  Google Scholar 

  2. Holland GF, Pereira JN (1967) J Med Chem 10:149

    Article  CAS  Google Scholar 

  3. Figdor SK, von Wittenau MS (1967) J Med Chem 10:1158

    Article  CAS  Google Scholar 

  4. Esplin DW, Woodbury DM (1956) J Pharmacol Exp Ther 118:129

    CAS  Google Scholar 

  5. Flippin LA (1991) Tetrahedron Lett 32:6857

    Article  CAS  Google Scholar 

  6. Rhonnstad P, Wensbo D (2002) Tetrahedron Lett 43:3137

    Article  CAS  Google Scholar 

  7. Ek F, Wistrand LG, Frejd T (2003) Tetrahedron 59:6759

    Article  CAS  Google Scholar 

  8. Sandmann G, Schneider C, Boger PZ (1996) Z Naturforsch C: J Biosci 51:534

    CAS  Google Scholar 

  9. Jursic BS, LeBlanc BW (1998) J Heterocycl Chem 35:405

    Article  CAS  Google Scholar 

  10. Zhao-Xu C, Heming X (2000) Int J Quantum Chem 79:350

    Article  Google Scholar 

  11. Hansch C, Leo L (1995) Exploring QSAR. Fundamentals and applications in chemistry and biology, chapter 13. American Chemical Society, Washington, DC

  12. Kadaba PK (1973) Synthesis 71

  13. Wittenberger SJ (1994) Org Prep Proced Int 26:499

    Article  CAS  Google Scholar 

  14. Curran DP, Hadida S, Kim SY (1999) Tetrahedron 55:8997

    Article  CAS  Google Scholar 

  15. Huff BE, Staszak MA (1993) Tetrahedron Lett 34:8011

    Article  CAS  Google Scholar 

  16. Habibi D, Nasrollahzadeh M (2012) Synth Commun 42:2023

    Article  CAS  Google Scholar 

  17. Zimmerman DM, Olofson RA (1969) Tetrahedron Lett 58:5081

    Article  Google Scholar 

  18. Fallon FG, Herbst RM (1957) J Org Chem 22:933

    Article  CAS  Google Scholar 

  19. Jin T, Kamijo S, Yamamoto Y (2004) Tetrahedron Lett 45:9435

    Article  CAS  Google Scholar 

  20. Satoh Y, Marcopulos N (1995) Tetrahedron Lett 36:1759

    Article  CAS  Google Scholar 

  21. Gupta AK, Oh CH (2004) Tetrahedron Lett 45:4113

    Article  CAS  Google Scholar 

  22. Su W, Hong Z, Shan W, Zhang X (2006) Eur J Org Chem 2733

  23. Butler RN (1977) Adv Het Chem 21:323

    CAS  Google Scholar 

  24. Kantam ML, Shiva Kumar KB, Sridhar C (2005) Adv Synth Catal 347:1212

    Google Scholar 

  25. Jin T, Kitahara F, Kamijo S, Yamamoto Y (2008) Tetrahedron Lett 49:2824

    Article  CAS  Google Scholar 

  26. Demko PZ, Sharpless KB (2001) J Org Chem 66:7945

    Article  CAS  Google Scholar 

  27. Himo F, Demko PZ, Noodleman L, Sharpless KB (2002) J Am Chem Soc 124:12210

    Article  CAS  Google Scholar 

  28. Himo F, Demko PZ, Noodleman L, Sharpless KB (2003) J Am Chem Soc 125:9983

    Article  CAS  Google Scholar 

  29. Loupy A, Petit A, Ramdiani M, Yvanae C, Majdoud M, Labiad B, Villemin D (1993) Can J Chem 71:90

    Article  CAS  Google Scholar 

  30. Loupy A, Maurel F, Sabatie-Gogova A (2004) Tetrahedron 60:1683

    Article  CAS  Google Scholar 

  31. Pchelka BK, Loupy A, Petit A (2006) Tetrahedron 62:10968

    Article  CAS  Google Scholar 

  32. Varma RS, Chatterjee AK, Varma M (1993) Tetrahedron Lett 34:3207

    Article  CAS  Google Scholar 

  33. Kumar D, Sundaree MS, Patel G, Rao VS, Varma RS (2006) Tetrahedron Lett 47:8239

    Article  CAS  Google Scholar 

  34. Kumar D, Sundaree S, Rao VS, Varma RS (2006) Tetrahedron Lett 47:4197

    Article  CAS  Google Scholar 

  35. Polshettiwar V, Kaushik MP (2004) Tetrahedron Lett 45:6255

    Article  CAS  Google Scholar 

  36. Blass BE (2002) Tetrahedron 58:9301

    Article  CAS  Google Scholar 

  37. Massah AR, Dabagh M, Shahidi S, Javaherian Naghash H, Momeni AR, Aliyan H (2003) J Chin Chem Soc 12:763

    Google Scholar 

  38. Mohammadizadeh MR, Hasaninejad A, Bahramzadeh M, Sardari Khanjarlou Z (2009) Synth Commun 39:1152

  39. Eshghi H, Shafieyoon P (2004) Phosphorus. Sulfur Silicon Relat Elem 179:2149

    Article  CAS  Google Scholar 

  40. Abdul R, Saloni G, Shweta S (2008) J Chem Res (S) 26:699

    Google Scholar 

  41. Hajipour AR, Ruoho AE (2005) Tetrahedron Lett 46:8307

    Article  CAS  Google Scholar 

  42. Hasaninejad A, Zare A, Sharghi H, Niknam K, Shekouhy M (2005) Arkivoc xiv:39

  43. Tamaddon F, Khoobi M, Keshavarz E (2007) Tetrahedron Lett 48:3643

    Article  CAS  Google Scholar 

  44. Mason TJ, Peters D (2002) Practical Sonochemistry, 2nd edn. Ellis Horwood, London

    Book  Google Scholar 

  45. Li JT, Yang WZ, Wang SX, Li SH, Li TS (2002) Ultrason Sonochem 9:237

    Article  CAS  Google Scholar 

  46. Wang SX, Li JT, Yang WZ, Li TS (2002) Ultrason Sonochem 9:159

    Article  Google Scholar 

  47. Wang SX, Li XW, Li JT (2008) Ultrason Sonochem 15:33

    Article  CAS  Google Scholar 

  48. Cave GWV, Raston CL, Scott JL (2001) Chem Commun 21:2159

    Article  Google Scholar 

  49. Habibi D, Nasrollahzadeh M, Kamali TA (2011) Green Chem 13:3499

    Article  CAS  Google Scholar 

  50. Habibi D, Nasrollahzadeh M (2012) Monatsh Chem 143:925

    Article  CAS  Google Scholar 

  51. Habibi D, Nasrollahzadeh M (2010) Synth Commun 40:3159

    Article  CAS  Google Scholar 

  52. Mohammadi B, Hosseini Jamkarani SM, Kamali TA, Nasrollahzadeh M, Mohajeri A (2010) Turk J Chem 34:613

    Google Scholar 

  53. Habibi D, Nasrollahzadeh M, Faraji AR, Bayat Y (2010) Tetrahedron 66:3866

    Article  CAS  Google Scholar 

  54. Nasrollahzadeh M, Bayat Y, Habibi D, Moshaee S (2009) Tetrahedron Lett 50:4435

    Article  CAS  Google Scholar 

  55. Nasrollahzadeh M, Habibi D, Shahkarami Z, Bayat Y (2009) Tetrahedron 66:3866

    Google Scholar 

  56. Kamali TA, Habibi D, Nasrollahzadeh M (2009) Synlett 2601

  57. Kamali TA, Bakherad M, Nasrollahzadeh M, Farhangi S, Habibi D (2009) Tetrahedron Lett 50:5459

    Article  CAS  Google Scholar 

  58. Habibi D, Nasrollahzadeh M, Bayat Y (2011) Synth Commun 41:2135

    Article  CAS  Google Scholar 

  59. Potewar TM, Siddiqui SA, Lahoti RJ, Srinivasan KV (2007) Tetrahedron Lett 48:1721

    Article  CAS  Google Scholar 

  60. Aridoss G, Laali KK (2011) Eur J Org Chem 2827

  61. Kuppa R, Moholkar VS (2010) Ultrason Sonochem 17:123

    Article  CAS  Google Scholar 

  62. Koda S, Kimurab T, Kondoc T, Mitomed H (2003) Ultrason Sonochem 13:149

    Article  Google Scholar 

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Acknowledgments

The authors gratefully acknowledge the financial support from the Bu-Ali Sina University, Hamedan 6517838683, Iran.

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Authors and Affiliations

  1. Faculty of Chemistry, Bu-Ali Sina University, 6517838683, Hamedan, Iran

    Davood Habibi, Leila Mehrabi & Samaneh Mostafaee

  2. Department of Chemistry, Faculty of Science, University of Qom, PO Box 37185-359, Qom, Iran

    Mahmoud Nasrollahzadeh

Authors
  1. Davood Habibi
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  2. Mahmoud Nasrollahzadeh
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  3. Leila Mehrabi
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  4. Samaneh Mostafaee
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Corresponding authors

Correspondence to Davood Habibi or Mahmoud Nasrollahzadeh.

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Habibi, D., Nasrollahzadeh, M., Mehrabi, L. et al. P2O5–SiO2 as an efficient heterogeneous catalyst for the solvent-free synthesis of 1-substituted 1H-1,2,3,4-tetrazoles under conventional and ultrasound irradiation conditions. Monatsh Chem 144, 725–728 (2013). https://doi.org/10.1007/s00706-012-0871-9

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  • DOI: https://doi.org/10.1007/s00706-012-0871-9

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