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Synthesis of new 4-(1,2,3-triazolo)quinolin-2(1H)-ones via Cu-catalyzed [3 + 2] cycloaddition

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Abstract

In this investigation, new classes of 1,2,3-triazoles derived by 2-quinolone have been synthesized, via Cu-catalyzed [3 + 2] cycloadditions (Meldal-Sharpless ‘click’ reactions) of 4-azidoquinolin-2(1H)-ones with some alkynes. The structures of the products have been confirmed by different spectroscopic analyses.

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References

  1. Chung PY, Bian ZX, Pun HY, Chan D, Chan ASC (2015) Future Med Chem 7:947

    Article  CAS  PubMed  Google Scholar 

  2. Faraz KM, Garima V, Wasim A, Akranth M, Mumtaz AM (2017) Int J Drug Develop Res 9:22

    CAS  Google Scholar 

  3. Agalave SG, Maujan SR, Pore VS (2011) Chem Asian J 6:2696

    Article  CAS  PubMed  Google Scholar 

  4. Dhee D, Singh V, Shankar R (2017) Bioorg Chem 71:30

    Article  CAS  Google Scholar 

  5. Chen YL, Fang KC, Sheu JY, Hsu SL, Tzeng CC (2001) J Med Chem 44:2374

    Article  CAS  PubMed  Google Scholar 

  6. Abass M, Hassanin HM, Allimony HA, Hassan H (2015) Chem Heterocycl Compd 51:1023

    Article  CAS  Google Scholar 

  7. Abass M, Mostafa BB (2005) Bioorg Med Chem 13:6133

    Article  CAS  PubMed  Google Scholar 

  8. Eswaran S, Adhikari AV, Chowdhury IH, Pal NK, Thomas KD (2010) Eur J Med Chem 45:3374

    Article  CAS  PubMed  Google Scholar 

  9. Musiol R, Jampilek J, Buchta V, Silva L, Niedbala H, Podeszwa B, Palka A, Majerz-Maniecka K, Oleksyn B, Polanski (2006) J Bioorg Med Chem 14:3592

    Article  CAS  Google Scholar 

  10. Al-Trawneh SA, Zahra JA, Kamal MR, El-Abadelah MM, Zani F, Incerti M, Cavazzoni A, Alfieri RR, Petronini PG, Vicini P (2010) Bioorg Med Chem 18:5873

    Article  CAS  PubMed  Google Scholar 

  11. Ahmed N, Brahmbhatt KG, Sabde S, Mitra D, Singh IP, Bhutani KK (2010) Med Chem 18:2872

    Article  CAS  Google Scholar 

  12. Sankaran M, Kumarasamy C, Chokkalingam U, Mohan PS (2010) Bioorg Med Chem Lett 20:7147

    Article  CAS  PubMed  Google Scholar 

  13. Slater AFG, Cerami A (1992) Nature (London) 355:167

    Article  CAS  Google Scholar 

  14. Ma Z, Hano Y, Nomura T, Chen Y (2004) Bioorg Med Chem Lett 14:1193

    Article  CAS  PubMed  Google Scholar 

  15. Agalave SG, Maujan SR, Pore VS (2011) Chem Asian J 6:2696

    Article  CAS  PubMed  Google Scholar 

  16. Ganesh A (2013) Int J Chem Sci 11:573

    CAS  Google Scholar 

  17. Tornøe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057

    Article  CAS  PubMed  Google Scholar 

  18. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596

    Article  CAS  Google Scholar 

  19. Kolb HC, Finn MG, Sharpless KB (2001) Angew Chem Int Ed 40:2004

    Article  CAS  Google Scholar 

  20. Meldal M, Tornøe CW (2008) Chem Rev 108:2952

    Article  CAS  PubMed  Google Scholar 

  21. Bock VD, Hiemstra H, van Maarseveen JH (2006) Eur J Org Chem 2006:51

    Article  CAS  Google Scholar 

  22. Goddard-Borger ED, Stick RV (2007) Org Lett 9:3797

    Article  CAS  PubMed  Google Scholar 

  23. Zhang X, Hsung RP, Li H (2007) Chem Commun 24:20

    Google Scholar 

  24. Zhang J, Chen H-N, Chiang F-I, Takemoto JY, Bensaci M, Chang C-WT (2007) J Comb Chem 9:17

    Article  CAS  PubMed  Google Scholar 

  25. Jasinski R (2015) Monatsh Chem 146:591

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. El-Sheref EM, Aly AA, Mourad A-FE, Brown AB, Bräse S, Bakheet MEM (2018) Chem Pap 72:181

    Article  CAS  Google Scholar 

  27. Aly AA, El-Sheref EM, Mourad A-FE, Brown AB, Bräse S, Bakheet MEM, Nieger M (2018) Monatsh Chem 149:635

    Article  CAS  Google Scholar 

  28. Aly AA, El-Sheref EM, Mourad A-FE, Brown AB, Bräse S, Bakheet MEM, Nieger M (2018) Chem Pap. https://doi.org/10.1007/s11696-018-0561-0

    Article  Google Scholar 

  29. Aly AA, El-Sheref EM, Bakheet MEM, Mourad MAE, Brown AB, Bräse S, Nieger M, Ibrahim MAA (2018) Bioorg Chem 81:700

    Article  CAS  PubMed  Google Scholar 

  30. Aly AA, El-Sheref EM, Bakheet MEM, Mourad MAE, Brown AB, Bräse S, Nieger M, Ibrahim MAA, Garvalov BK, Dalby KN, Kaoud TS (2019) Bioorg Chem 82:290

    Article  CAS  PubMed  Google Scholar 

  31. (a) Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596; (b) Himo F, Lovell T, Hilgraf R, Rostovtsev VV, Noodleman L, Sharpless KB, Fokin VV (2005) J Am Chem Soc 127:210

  32. Steinschifter W, Stadlbauer W (1994) J Prakt Chem 336:311

    Article  CAS  Google Scholar 

  33. Aizikovich A, Kuznetsov V, Gorohovsky S, Levy A, Meir S, Byk G, Gellerman GA (2004) Tetrahedron Lett 45:4241

    Article  CAS  Google Scholar 

  34. Liu SJ, Zhou B, Yang H, He Y, Jiang Z-X, Kumar S, Wu L, Zhang Y-Z (2008) J Am Chem Soc 130:8251

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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Acknowledgements

The NMR spectrometer at Florida Institute of Technology was purchased with assistance from the US National Science Foundation (CHE 03-42251).

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Correspondence to Ashraf A. Aly.

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El-Sheref, E.M., Aly, A.A., Ameen, M.A. et al. Synthesis of new 4-(1,2,3-triazolo)quinolin-2(1H)-ones via Cu-catalyzed [3 + 2] cycloaddition. Monatsh Chem 150, 747–756 (2019). https://doi.org/10.1007/s00706-018-2342-4

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  • DOI: https://doi.org/10.1007/s00706-018-2342-4

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