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Green chemistry: ZrOCl2·8H2O catalyzed regioselective synthesis of 5-amino-1-aryl-1H-tetrazoles from secondary arylcyanamides in water

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Abstract

A green and efficient method for the synthesis of 5-amino-1-aryl-1H-tetrazoles with excellent yields and high purity from secondary arylcyanamides is described. This method is completely green because no organic solvents or protic acid catalyst is used that can generate hydrazoic acid (HN3). In addition, it is a very clean method for acquiring 5-amino-1-aryl-1H-tetrazoles without generating 5-arylamino-1H(2H)-tetrazoles in most cases.

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References

  1. Butler RN, Katritzky AR, Rees CW, Scriven EFV (1996) Comprehensive heterocyclic chemistry, vol 4. Pergamon, Oxford

    Google Scholar 

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

    Article  CAS  Google Scholar 

  3. Monderhack D (1998) J Prakt Chem 340:687

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  5. Benson FR (1947) Chem Rev 47:1

    Article  Google Scholar 

  6. Koldobskii GI, Ostrovskii VA, Popavskii VS (1981) Chem Heterocycl Comp 17:965

    Google Scholar 

  7. Butler RN (1977) Adv Heterocycl Chem 21:323

    Article  CAS  Google Scholar 

  8. Modarresi Alam AR, Nasrollahzadeh M (2009) Turk J Chem 33:267

    CAS  Google Scholar 

  9. Hodges JC, Hamby JM, Blankley CJ (1992) Drugs Future 17:575

    Google Scholar 

  10. Satchell JF, Smith BJ (2002) Phys Chem Chem Phys 4:4314

    Article  CAS  Google Scholar 

  11. Singh H, Chawla AS, Kapoor VK, Paul D (1980) Prog Med Chem 17:151

    Article  CAS  Google Scholar 

  12. Jursic BS, Blanc BW (1998) J Heterocycl Chem 35:405

    Article  CAS  Google Scholar 

  13. Kharaghiosoff K, Klapotke TM, Mayer P (2006) J Org Chem 71:1295

    Article  Google Scholar 

  14. Wexler RR, Greenlee WJ, Irvin JD (1996) J Med Chem 39:625

    Article  CAS  Google Scholar 

  15. Sproat B, Colonna F, Mullah B (1995) Nucleosides Nucleotides 14:255

    Article  CAS  Google Scholar 

  16. Desarro A, Ammendola D, Zappala M (1995) Antimicorb Agents Chemother 39:232

    Article  CAS  Google Scholar 

  17. Wood E, Crosby RM, Dickerson S (2001) Anti-Cancer Drug Des 16:1

    CAS  Google Scholar 

  18. May BCH, Abell AD (2002) J Chem Soc Perkin Trans 1:172

    Google Scholar 

  19. Modarresi-Alam AR, Khamooshi F, Rostamizadeh M (2007) J Mol Struc 841:61

    Article  CAS  Google Scholar 

  20. Katritzky AR, Rogovoy BV, Kovalenko KV (2003) J Org Chem 68:4941

    Article  CAS  Google Scholar 

  21. Demko PZ, Sharpless KB (2001) Org Lett 3:4091

    Article  CAS  Google Scholar 

  22. Miller AE, Feeney DJ, Ma Y, Zircon L, Aziz MA, Magnuson E (1990) Synth Commun 20:217

    Article  CAS  Google Scholar 

  23. Schelenz T, Schäfer W (2000) J Prakt Chem 342:197

    Article  CAS  Google Scholar 

  24. Lenarsic R, Kocevar M, Polanc S (1999) J Org Chem 64:2558

    Article  CAS  Google Scholar 

  25. Firouzabadi H, Iranpoor N, Karimi B (1999) Synlett 1999(3):319

  26. Chary KP, Mohan GH, Iyengar DS (1999) Chem Lett 12:1339

    Article  Google Scholar 

  27. Chary KP, Ram SR (2000) Synlett 2000(5):683

  28. Karimi B, Seradj H (2000) Synlett 2000(6):805

  29. Tsuji C, Miyazawa E, Sakamoto T (2002) Synth Commun 32:3871

    Article  CAS  Google Scholar 

  30. Smitha G, Patnaik S, Reddy CS (2005) Synthesis 2005(5):711

  31. Chakraborti AK, Kondaskar A (2003) Tetrahedron Lett 44:8315

    Article  CAS  Google Scholar 

  32. Shi M, Cui SC, Li QJ (2004) Tetrahedron 60:6679

    Article  CAS  Google Scholar 

  33. Bora U (2003) Synlett 2003(7):1073

  34. Mo LP, Zhang ZH (2011) Curr Org Chem 15:3800

    Article  CAS  Google Scholar 

  35. Zhang ZH, Li TS (2009) Curr Org Chem 13:1

    Article  CAS  Google Scholar 

  36. Lu HY, Li JJ, Zhang ZH (2009) Appl Organomet Chem 23:165

    Article  CAS  Google Scholar 

  37. Karami B, Kiani M (2011) Catal Commun 14:62

    Article  CAS  Google Scholar 

  38. Fioravanti S, Pellacani L, Vergari MC (2012) Org Biomol Chem 10:8207

    Article  CAS  Google Scholar 

  39. Movassagh B, Rakhshani A (2012) Synth Commun 42:2121

    Article  CAS  Google Scholar 

  40. Eftekhari-Sis B, Abdollahifar A, Hashemi MM, Zirak M (2006) Eur J Org Chem 2006(22):5152

  41. Hashemi MM, Eftekhari-Sis B, Abdollahifar A, Khalili B (2006) Tetrahedron 62:672

    Article  CAS  Google Scholar 

  42. Matloubi Moghaddam F, Ismaili H, Rezanejade Bardajee G (2006) Heteroat Chem 17:136

    Article  Google Scholar 

  43. Anderson AM, Blazek JM, Garg P (2000) Tetrahedron Lett 41:1527

    Article  CAS  Google Scholar 

  44. Crutchley RJ, Nakicki ML (1989) Inorg Chem 28:1955

    Article  CAS  Google Scholar 

  45. Niwa R, Kamada H, Shitara E (1996) Chem Pharm Bull 44:2314

    Article  CAS  Google Scholar 

  46. Butler RN, Garvin NL (1981) J Chem Soc Perkin Trans 1:390

    Article  Google Scholar 

  47. Butler RN, Mc Evoy TM, Scott FL (1977) Can J Chem 55:1564

    Article  CAS  Google Scholar 

  48. Butler RN (1972) Can J Chem 51:2315

    Article  Google Scholar 

  49. Batterhan TJ (1973) NMR spectra of simple heterocycles. Wiley, New York, p 226

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, University of Guilan, P.O. Box 41335-1914, Rasht, Iran

    Behzad Khalili

  2. Young Researcher Club, Parsabad Moghan Branch, Islamic Azad University, Parsabad, Iran

    Faramarz Sadeghzadeh Darabi

  3. Department of Chemistry, University of Maragheh, P. O. Box 55181-83111, Maragheh, Iran

    Bagher Eftekhari-Sis

  4. Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran

    Mehdi Rimaz

Authors
  1. Behzad Khalili
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  2. Faramarz Sadeghzadeh Darabi
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  3. Bagher Eftekhari-Sis
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  4. Mehdi Rimaz
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Corresponding author

Correspondence to Behzad Khalili.

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Khalili, B., Darabi, F.S., Eftekhari-Sis, B. et al. Green chemistry: ZrOCl2·8H2O catalyzed regioselective synthesis of 5-amino-1-aryl-1H-tetrazoles from secondary arylcyanamides in water. Monatsh Chem 144, 1569–1572 (2013). https://doi.org/10.1007/s00706-013-1038-z

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  • DOI: https://doi.org/10.1007/s00706-013-1038-z

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