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One-pot synthesis of novel s-triazine-containing polyphenols and imidazotriazinium salts

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Abstract

Study of the reaction of aminoacetal containing 1,3,5-triazine moiety with phenols is reported. Reaction conditions leading to the formation of either polyphenols modified with 1,3,5-triazine moiety or previously unknown 6-arylimidazo[1,2-a][1,3,5]triazin-5-ium salts with good yields are determined. Formation of triazinium salts proceeds via the dearylation of initially formed triazine-containing polyphenols.

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References

  1. von Baeyer A (1872) Ber Dtsch Chem Ges 5:25

    Google Scholar 

  2. Durairaj RB (2005) In: Resorcinol. Springer, Berlin, p 179

    Google Scholar 

  3. Hoegberg AGS (1980) J Am Chem Soc 102:6046

    Article  CAS  Google Scholar 

  4. Hoegberg AGS (1980) J Org Chem 45:4498

    Article  Google Scholar 

  5. Hinsberg O (1923) Ber Dtsch Chem Ges 56:852

    Article  Google Scholar 

  6. Plażuk D, Zakrzewski J (2005) Phosphorus. Sulfur Silicon Relat Elem 180:2709

    Article  Google Scholar 

  7. Gazizov AS, Burilov AR, Khakimov MS (2009) Russ Chem Bull Int Ed 58:238

    Article  CAS  Google Scholar 

  8. Gazizov AS, Burilov AR, Khakimov MS, Kharitonova NI, Pudovik MA, Konovalov AI (2009) Russ J Gen Chem 79:1929

    Article  CAS  Google Scholar 

  9. Burilov AR, Gazizov AS, Pudovik MA, Konovalov AI (2007) Russ J Gen Chem 77:98

    Article  CAS  Google Scholar 

  10. Burilov AR, Gazizov AS, Volodina YM, Pudovik MA, Habicher WD, Bauer I, Gubaidullin AT, Litvinov IA, Konovalov AI (2005) Mendeleev Commun 15:153

    Article  Google Scholar 

  11. Burilov AR, Gazizov AS, Kharitonova NI, Pudovik MA, Konovalov AI (2007) Russ J Gen Chem 77:487

    Article  CAS  Google Scholar 

  12. Burilov AR, Knyazeva IR, Kasymova EM, Sadykova YM, Pudovik MA, Sinyashin OG, Habicher WD (2011) Phosphorus. Sulfur Silicon Relat Elem 186:884

    Article  CAS  Google Scholar 

  13. Baliani A, Bueno GJ, Stewart ML, Yardley V, Brun R, Barrett MP, Gilbert IH (2005) J Med Chem 48:5570

    Article  CAS  Google Scholar 

  14. Pandey VK, Tusi S, Tusi Z, Joshi M, Bajpai S (2004) Acta Pharm (Zagreb, Croatia) 54:1

  15. Srinivas K, Srinivas U, Rao VJ, Bhanuprakash K, Kishore KH, Murty USN (2005) Bioorg Med Chem Lett 15:1121

    Article  CAS  Google Scholar 

  16. Rose Y, Ciblat S, Reddy R, Belley AC, Dietrich E, Lehoux D, McKay G, Poirier H, Far AR, Delorme D (2006) Bioorg Med Chem Lett 16:891

    Article  CAS  Google Scholar 

  17. Ghaib A, Menager S, Verite P, Lafont O (2002) Farmaco 57:109

    Article  CAS  Google Scholar 

  18. Lübbers T, Angehrn P, Gmünder H, Herzig S, Kulhanek J (2000) Bioorg Med Chem Lett 10:821

    Article  Google Scholar 

  19. Lebreton S, Newcombe N, Bradley M (2003) Tetrahedron 59:10213

    Article  CAS  Google Scholar 

  20. Jensen NP, Ager L, Bliss R, Canfield CJ, Kotecka BM, Rieckmann KH, Terpinski J, Jacobus DP (2001) J Med Chem 44:3925

    Article  CAS  Google Scholar 

  21. Agarwal A, Srivastava K, Puri SK, Chauhan PMS (2005) Bioorg Med Chem Lett 15:531

    Article  CAS  Google Scholar 

  22. Menicagli R, Samaritani S, Signore G, Vaglini L, Via D (2004) J Med Chem 47:4649

    Article  CAS  Google Scholar 

  23. Henke BR, Consler TG, Go N, Hale RL, Hohman DR, Jones S, Lu AT, Moore LB, Moore JT, Orband-Miller L, Robinett RG, Shearin J, Spearing PK, Stewart EL, Turnbull PS, Weaver SL, Williams SP, Wisely GB, Lambert MH (2002) J Med Chem 45:5492

    Article  CAS  Google Scholar 

  24. Kuo GH, Deangelis A, Emanuel S, Wang A, Zhang Y, Connolly PJ, Chen X, Gruninger RH, Rugg C, Fuentes-Pesquera A, Middleton SA, Jolliffe L, Murray WV (2005) J Med Chem 48:4535

    Article  CAS  Google Scholar 

  25. Matsuno T, Kato M, Tsuchida Y, Takahashi M, Yaguchi S, Terada S (1997) Chem Pharm Bull 45:291

    Article  CAS  Google Scholar 

  26. Eliazyan KA, Akopyan AM, Pivazyan VA, Akopyan AG, Dovlatyan VV (1992) Chem Heterocycl Compd 28:188

    Article  Google Scholar 

  27. Okide GB (1994) J Heterocycl Chem 31:535

    Article  CAS  Google Scholar 

  28. Hinkens R, Promel R, Martin RH (1961) Helv Chim Acta 44:299

    Article  CAS  Google Scholar 

  29. Dovlatyan VV, Dovlatyan AV (1979) Chem Heterocycl Compd 15:111

    Article  Google Scholar 

  30. Dovlatyan VV (1996) Chem Heterocycl Compd 32:375

    Article  Google Scholar 

Download references

Acknowledgments

This work was supported by the Russian Foundation for Basic Research (Project No. 12-03-31138-a-mol).

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Authors and Affiliations

  1. A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Centre, Russian Academy of Sciences, Kazan, Russia

    Almir S. Gazizov, Natalya I. Kharitonova, Alexander R. Burilov, Michail A. Pudovik & Oleg G. Sinyashin

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  1. Almir S. Gazizov
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  2. Natalya I. Kharitonova
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  3. Alexander R. Burilov
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  4. Michail A. Pudovik
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  5. Oleg G. Sinyashin
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Correspondence to Almir S. Gazizov.

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Gazizov, A.S., Kharitonova, N.I., Burilov, A.R. et al. One-pot synthesis of novel s-triazine-containing polyphenols and imidazotriazinium salts. Monatsh Chem 144, 1027–1030 (2013). https://doi.org/10.1007/s00706-013-0939-1

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  • DOI: https://doi.org/10.1007/s00706-013-0939-1

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