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Facile synthesis of N-acylbenzotriazoles from carboxylic acids mediated by 2,4,6-trichloro-1,3,5-triazine and triethylamine

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Abstract

A facile, efficient, and economic method toward N-acylbenzotriazoles was reported using 2,4,6-trichloro-1,3,5-triazine in combination with triethylamine as a carboxylic acid activator. Through reacting 1H-benzotriazole with the generated triacylated triazine intermediate, a series of N-acylbenzotriazoles could be rapidly prepared in high yields without column chromatography.

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References

  1. Katritzky AR, Rogovoy BV, Kirichenko N, Vvedensky V (2002) Bioorg Med Chem Lett 12:1809

    Article  CAS  Google Scholar 

  2. Katritzky AR, Suzuki K, Singh SK, He H-Y (2003) J Org Chem 68:5720

    Article  CAS  Google Scholar 

  3. Wang X, Zhang Y (2003) Synth Commun 33:2627

    Article  CAS  Google Scholar 

  4. Katritzky AR, Abdel-Fattah AAA, Wang M (2003) J Org Chem 68:4932

    Article  CAS  Google Scholar 

  5. Katritzky AR, Abdel-Fattah AAA, Wang M (2003) J Org Chem 68:1443

    Article  CAS  Google Scholar 

  6. Katritzky AR, Shestopalov AA, Suzuki K (2004) Synthesis 1806

  7. Katritzky AR, Cai C, Suzuki K, Singh SK (2004) J Org Chem 69:811

    Article  CAS  Google Scholar 

  8. Katritzky AR, Abdel-Fattah AAA, Gromova AV, Witek R, Steel PJ (2005) J Org Chem 70:9211

    Article  CAS  Google Scholar 

  9. Katritzky AR, Suzuki K, Wang Z (2005) Synlett 1656

  10. Katritzky AR, Widyan K, Kirichenko K (2007) J Org Chem 72:5802

    Article  CAS  Google Scholar 

  11. Lim D, Fang F, Zhou G, Coltart DM (2007) Org Lett 9:4139

    Article  CAS  Google Scholar 

  12. Wang X, Wang W, Wen Y, He L, Zhu X (2008) Synthesis 3223

  13. Zhou G, Lim D, Fang F, Coltart DM (2009) Synthesis 3350

  14. Li J, Sun Y, Chen Z, Su W (2010) Synth Commun 40:3669

    Article  CAS  Google Scholar 

  15. Xia Z, Lv X, Wang W, Wang X (2011) Tetrahedron Lett 52:4906

    Article  CAS  Google Scholar 

  16. Katritzky AR, He H-Y, Suzuki K (2000) J Org Chem 65:8210

    Article  CAS  Google Scholar 

  17. Katritzky AR, Zhang Y, Singh SK (2003) Synthesis 2795

  18. Duangkamol C, Wangngae S, Pattarawarapan M, Phakhodee W (2014) Eur J Org Chem 7109

  19. Blotny G (2006) Tetrahedron 62:9507

    Article  CAS  Google Scholar 

  20. Kaminski ZJ (2000) Biopolymers 55:140

    Article  CAS  Google Scholar 

  21. Kolesinska B, Kaminski ZJ (2009) Tetrahedron 65:3573

    Article  CAS  Google Scholar 

  22. Katritzky AR, Shobana N, Pernak J, Afridi AS, Fan WQ (1992) Tetrahedron 48:7817

    Article  CAS  Google Scholar 

  23. Nakamura I, Nemoto T, Shiraiwa N, Terada M (2009) Org Lett 11:1055

    Article  CAS  Google Scholar 

  24. Asakawa T, Hiza A, Nakayama M, Inai M, Oyama D, Koide H, Shimizu K, Wakimoto T, Harada N, Tsukada H, Oku N, Kan T (2011) Chem Commun 47:2868

    Article  CAS  Google Scholar 

  25. Lin S-M, Zhang J-L, Chen J-X, Gao W-X, Ding J-C, Su W-K, Wu H-Y (2010) J Braz Chem Soc 21:1616

    Article  CAS  Google Scholar 

  26. Katritzky AR, Le KNB, Khelashvili L, Mohapatra PP (2006) J Org Chem 71:9861

    Article  CAS  Google Scholar 

  27. Pardin C, Pelletier JN, Lubell WD, Keillor JW (2008) J Org Chem 73:5766

    Article  CAS  Google Scholar 

  28. Nagel MCV, Heinze T (2010) Polym Bull 65:873

    Article  CAS  Google Scholar 

  29. Katritzky AR, Wang Z, Slavov S, Tsikolia M, Dobchev D, Akhmedov NG, Hall CD, Bernier UR, Clark GG, Linthicum KJ (2008) Proc Natl Acad Sci 105:7359

    Article  CAS  Google Scholar 

  30. Venkataraman K, Wagle DR (1979) Tetrahedron Lett 3037

  31. Lahoti RJ, Wagle DR (1981) Ind J Chem 20:852

    Google Scholar 

  32. Luo G, Xu L, Poindexter GS (2002) Tetrahedron Lett 43:8909

    Article  CAS  Google Scholar 

  33. Rayle HL, Fellmeth L (1999) Org Process Res Dev 3:172

  34. de Luca L, Giacomelli G, Taddei M (2001) J Org Chem 66:2534

    Article  Google Scholar 

  35. Bandgar B, Sawant S (2006) Synth Commun 36:859

    Article  CAS  Google Scholar 

  36. Khalafi-Nezhad A, Zare A, Parhami A, Rad MNS, Nejabat GR (2007) Phosphorus, Sulfur Silicon Relat Elem 182:657

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The Center of Excellence for Innovation in Chemistry (PERCH-CIC), and the National Research University Project under Thailand’s Office of the Higher Education Commission are gratefully acknowledged for financial support.

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Correspondence to Wong Phakhodee.

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Wet-osot, S., Duangkamol, C., Pattarawarapan, M. et al. Facile synthesis of N-acylbenzotriazoles from carboxylic acids mediated by 2,4,6-trichloro-1,3,5-triazine and triethylamine. Monatsh Chem 146, 959–963 (2015). https://doi.org/10.1007/s00706-014-1408-1

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  • DOI: https://doi.org/10.1007/s00706-014-1408-1

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