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Intensified synthesis of [3,4-d]triazole-fused chromenes, coumarins, and quinolones

Abstract

Efficient and metal-free synthesis of [3,4-d]triazole-fused chromenes, coumarins, and quinolones has been achieved in an intensified regime using microwave heating. The smooth 1,3-dipolar cycloaddition reaction of heterocyclic nitroalkenes with sodium azide provides a rapid entry into valuable heterocyclic scaffolds with potential biological properties.

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References

  1. 1.

    Borges F, Roleira F, Milhazes N, Santana L, Uriarte E (2005) Curr Med Chem 12:887

    CAS  Article  Google Scholar 

  2. 2.

    Lauria A, Delisi B, Mingoia F, Terenzi A, Martorana A, Barone G, Almerico AM (2014) Eur J Org Chem 2014:3289

    CAS  Article  Google Scholar 

  3. 3.

    Haider S, Alam SA, Hamid H (2014) Inflamm Cell Signal 1:e95

    Google Scholar 

  4. 4.

    Penq XM, Damu GL, Zhou C (2013) Curr Pharm Des 19:3884

    Article  Google Scholar 

  5. 5.

    Srikrishna D, Godugu C, Dubey PK (2016) Mini Rev Med Chem. doi:10.2174/1389557516666160801094919

    Google Scholar 

  6. 6.

    Drlica K, Hiasa H, Kerns R, Malik M, Mustaev A, Zhao X (2009) Curr Top Med Chem 9:981

    CAS  Article  Google Scholar 

  7. 7.

    Schiedel MS, Briehn CA, Bäuerle P (2001) Angew Chem Int Ed 40:4677

    CAS  Article  Google Scholar 

  8. 8.

    Glasnov TN, Kappe CO (2007) QSAR Comb Sci 26:1261 (and citations therein)

    CAS  Article  Google Scholar 

  9. 9.

    Shieh P, Bertozzi CR (2014) Org Biomol Chem 12:9307

    CAS  Article  Google Scholar 

  10. 10.

    Huisgen R (1963) Angew Chem Int Ed 2:565

    Article  Google Scholar 

  11. 11.

    Tornoe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057

    CAS  Article  Google Scholar 

  12. 12.

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

    CAS  Article  Google Scholar 

  13. 13.

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

    CAS  Article  Google Scholar 

  14. 14.

    Anisimova NA, Makarova NG, Berkova GA, Berestovitskaya VM (2006) Russ J Gen Chem 76:1545

    CAS  Article  Google Scholar 

  15. 15.

    Anisimova NA, Berestovitskaya VM, Berkova GA, Makarova NG (2007) Russ J Org Chem 43:652

    CAS  Article  Google Scholar 

  16. 16.

    Wang T, Hu XC, Huang XS, Li XS, Xie JW (2012) J Braz Chem Soc 6:1119

    Article  Google Scholar 

  17. 17.

    Mani NS, Fitzgerald AE (2014) J Org Chem 79:8889

    CAS  Article  Google Scholar 

  18. 18.

    Zhang H, Dong DQ, Wang ZL (2016) Synthesis 40:131

    Google Scholar 

  19. 19.

    Xiao GQ, Liang BX, Chen SH, Ou TM, Bu XZ, Yan M (2012) Arch Pharm Chem Life Sci 345:767

    CAS  Article  Google Scholar 

  20. 20.

    Bogdal D (1998) J Chem Res (S) 468

  21. 21.

    de la Hoz A, Loupy A (2012) Microwaves in organic synthesis, vol 1&2, 3rd edn. Wiley-VCH, Weinheim

    Book  Google Scholar 

  22. 22.

    Barton JW, Pearson ND (1987) J Chem Soc Perkin Trans 1:1541

    Article  Google Scholar 

  23. 23.

    Uno H, Okada SI, Shiraishi Y, Shinokawa K, Suzuki H (1988) Chem Lett 17:1165

    Article  Google Scholar 

  24. 24.

    Yan MC, Tu Z, Lin C, Ko S, Hsu J, Yao CF (2004) J Org Chem 69:1565

    CAS  Article  Google Scholar 

  25. 25.

    Sharma RK, Priyanka Katiyar D (2016) Monatsh Chem 147:2157

    CAS  Article  Google Scholar 

  26. 26.

    Dauzonne D, Royer R (1983) Synthesis 836

  27. 27.

    Dauzonne D, Royer R (1984) Eur J Med Chem 19:477

    CAS  Google Scholar 

  28. 28.

    Anderson WK, Dalvie DK (1993) J Heterocycl Chem 30:1533

    CAS  Article  Google Scholar 

  29. 29.

    Dauzonne D, Royer R (1984) Synthesis 348

  30. 30.

    Neirabeyeh MA, Koussini R, Guillaumet G (1990) Synth Commun 20:783

    Article  Google Scholar 

  31. 31.

    Ito K, Haryia J (1987) Heterocycles 26:35

    Article  Google Scholar 

  32. 32.

    D’Ambrosio G, Fringuelli F, Pizzo F, Vaccaro L (2005) Green Chem 7:874

    Article  Google Scholar 

Download references

Acknowledgements

Funding was provided by the Austrian Science Funds (FWF, Grant No. P28243-B27).

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Correspondence to Toma Glasnov.

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Schwendt, G., Glasnov, T. Intensified synthesis of [3,4-d]triazole-fused chromenes, coumarins, and quinolones. Monatsh Chem 148, 69–75 (2017). https://doi.org/10.1007/s00706-016-1885-5

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Keywords

  • Microwave-assisted synthesis
  • 1,3-Cycloaddition
  • Heterocycles
  • Catalyst-free