Monatshefte für Chemie - Chemical Monthly

, Volume 148, Issue 1, pp 69–75 | Cite as

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

  • Georg Schwendt
  • Toma GlasnovEmail author
Original Paper


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.

Graphical abstract

Open image in new window


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



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


  1. 1.
    Borges F, Roleira F, Milhazes N, Santana L, Uriarte E (2005) Curr Med Chem 12:887CrossRefGoogle Scholar
  2. 2.
    Lauria A, Delisi B, Mingoia F, Terenzi A, Martorana A, Barone G, Almerico AM (2014) Eur J Org Chem 2014:3289CrossRefGoogle Scholar
  3. 3.
    Haider S, Alam SA, Hamid H (2014) Inflamm Cell Signal 1:e95Google Scholar
  4. 4.
    Penq XM, Damu GL, Zhou C (2013) Curr Pharm Des 19:3884CrossRefGoogle 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 9:981CrossRefGoogle Scholar
  7. 7.
    Schiedel MS, Briehn CA, Bäuerle P (2001) Angew Chem Int Ed 40:4677CrossRefGoogle Scholar
  8. 8.
    Glasnov TN, Kappe CO (2007) QSAR Comb Sci 26:1261 (and citations therein) CrossRefGoogle Scholar
  9. 9.
    Shieh P, Bertozzi CR (2014) Org Biomol Chem 12:9307CrossRefGoogle Scholar
  10. 10.
    Huisgen R (1963) Angew Chem Int Ed 2:565CrossRefGoogle Scholar
  11. 11.
    Tornoe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057CrossRefGoogle Scholar
  12. 12.
    Kolb HC, Finn MG, Sharpless KB (2001) Angew Chem Int Ed 40:2004CrossRefGoogle Scholar
  13. 13.
    Rostovtsev VV, Green GL, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596CrossRefGoogle Scholar
  14. 14.
    Anisimova NA, Makarova NG, Berkova GA, Berestovitskaya VM (2006) Russ J Gen Chem 76:1545CrossRefGoogle Scholar
  15. 15.
    Anisimova NA, Berestovitskaya VM, Berkova GA, Makarova NG (2007) Russ J Org Chem 43:652CrossRefGoogle Scholar
  16. 16.
    Wang T, Hu XC, Huang XS, Li XS, Xie JW (2012) J Braz Chem Soc 6:1119CrossRefGoogle Scholar
  17. 17.
    Mani NS, Fitzgerald AE (2014) J Org Chem 79:8889CrossRefGoogle Scholar
  18. 18.
    Zhang H, Dong DQ, Wang ZL (2016) Synthesis 40:131Google Scholar
  19. 19.
    Xiao GQ, Liang BX, Chen SH, Ou TM, Bu XZ, Yan M (2012) Arch Pharm Chem Life Sci 345:767CrossRefGoogle Scholar
  20. 20.
    Bogdal D (1998) J Chem Res (S) 468Google Scholar
  21. 21.
    de la Hoz A, Loupy A (2012) Microwaves in organic synthesis, vol 1&2, 3rd edn. Wiley-VCH, WeinheimCrossRefGoogle Scholar
  22. 22.
    Barton JW, Pearson ND (1987) J Chem Soc Perkin Trans 1:1541CrossRefGoogle Scholar
  23. 23.
    Uno H, Okada SI, Shiraishi Y, Shinokawa K, Suzuki H (1988) Chem Lett 17:1165CrossRefGoogle Scholar
  24. 24.
    Yan MC, Tu Z, Lin C, Ko S, Hsu J, Yao CF (2004) J Org Chem 69:1565CrossRefGoogle Scholar
  25. 25.
    Sharma RK, Priyanka Katiyar D (2016) Monatsh Chem 147:2157CrossRefGoogle Scholar
  26. 26.
    Dauzonne D, Royer R (1983) Synthesis 836Google Scholar
  27. 27.
    Dauzonne D, Royer R (1984) Eur J Med Chem 19:477Google Scholar
  28. 28.
    Anderson WK, Dalvie DK (1993) J Heterocycl Chem 30:1533CrossRefGoogle Scholar
  29. 29.
    Dauzonne D, Royer R (1984) Synthesis 348Google Scholar
  30. 30.
    Neirabeyeh MA, Koussini R, Guillaumet G (1990) Synth Commun 20:783CrossRefGoogle Scholar
  31. 31.
    Ito K, Haryia J (1987) Heterocycles 26:35CrossRefGoogle Scholar
  32. 32.
    D’Ambrosio G, Fringuelli F, Pizzo F, Vaccaro L (2005) Green Chem 7:874CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Wien 2016

Authors and Affiliations

  1. 1.Institute of ChemistryUniversity of GrazGrazAustria

Personalised recommendations