Monatshefte für Chemie - Chemical Monthly

, Volume 147, Issue 12, pp 2157–2161 | Cite as

l-Proline catalyzed condensation of salicylaldehydes with ethyl nitroacetate: an efficient access to 3-nitrocoumarins

Original Paper

Abstract

l-Proline catalyzed condensation of salicylaldehydes and ethyl nitroacetate afforded 3-nitrocoumarins in good to high yields under mild conditions. This organocatalyzed process offers a much improved yield of 3-nitrocoumarins and well tolerates both electron-donating and electron-withdrawing substituents on the phenyl ring.

Graphical abstract

Keywords

Coumarins 3-Nitrocoumarins l-Proline Organocatalysis Salicylaldehyde 

Notes

Acknowledgments

The authors thank BHU, Varanasi for financial support. Priyanka is thankful to CSIR, New Delhi, India for Senior Research Fellowship.

Supplementary material

706_2016_1736_MOESM1_ESM.docx (2.5 mb)
Supplementary material 1 (DOCX 2562 kb)

References

  1. 1.
    Riveiro ME, De KN, Moglioni A, Vazquez R, Monczor F, Shayo C, Davio C (2010) Curr Med Chem 17:1325CrossRefGoogle Scholar
  2. 2.
    Hault JRS, Paya M (1996) Gen Pharmacol 27:713CrossRefGoogle Scholar
  3. 3.
    Mishra S, Singh LK, Priyanka, Gupta J, Misra-Bhattacharya S, Katiyar D (2015) Eur J Med Chem 94:211Google Scholar
  4. 4.
    Trenor SR, Shultz AR, Love BJ, Long TE (2004) Chem Rev 104:3059CrossRefGoogle Scholar
  5. 5.
    Sheng R, Wang P, Gao Y, Wu Y, Liu W, Ma J, Li H, Wu S (2008) Org Lett 10:5015CrossRefGoogle Scholar
  6. 6.
    Symeonidis T, Chamilos M, Hadjipavlou-Litina DJ, Kallitsakis M, Litinas KE (2009) Bioorg Med Chem Lett 19:1139CrossRefGoogle Scholar
  7. 7.
    Garazd MM, Garazd YL, Khilya VP (2005) Chem Nat Compd 41:245CrossRefGoogle Scholar
  8. 8.
    Zhang X-S, Li Z-W, Shi Z-J (2014) Org Chem Front 1:44CrossRefGoogle Scholar
  9. 9.
    Galm U, Heller S, Shapiro S, Page M, Li S-M, Heide L (2004) Antimicrob Agents Chemother 48:1307CrossRefGoogle Scholar
  10. 10.
    Xie J-W, Wang Z, Yang W-J, Kong L-C, Xu D-C (2009) Org Biomol Chem 7:4352CrossRefGoogle Scholar
  11. 11.
    Debeljak Ẑ, Krbo Š, Jasprica AI, Mornar A, Pleĉko V, Banjanac M, Medić-Šarić MJ (2007) Chem Inf Model 47:918CrossRefGoogle Scholar
  12. 12.
    Perrella FW, Chen S-F, Behrens DL, Kaltenbach RF III, Seitz SP (1994) J Med Chem 37:2232CrossRefGoogle Scholar
  13. 13.
    Bergsma JCT, Kasri NN, Donaton MCV, Wever VD, Tisi R, Winde JHD, Martegani E, Thevelein JM, Wera S (2001) Biochem J 359:517CrossRefGoogle Scholar
  14. 14.
    Tisi R, Coccetti P, Banfi S, Martegani E (2001) Cell Biochem Funct 19:229CrossRefGoogle Scholar
  15. 15.
    Dekić B, Dekić V, Radulović N, Vukićević R, Palić R (2010) Chem Pap 64:354Google Scholar
  16. 16.
    Marcu MG, Schulte TW, Neckers L (2000) J Natl Cancer Inst 92:242CrossRefGoogle Scholar
  17. 17.
    Melagraki G, Afantitis A, Igglessi-Markopoulou O, Detsi A, Koufaki M, Kontogiorgis C, Hadjipavlou-Litina DJ (2009) Eur J Med Chem 44:3020CrossRefGoogle Scholar
  18. 18.
    Das AR, Medda A, Singha R (2010) Tetrahedron Lett 51:1099CrossRefGoogle Scholar
  19. 19.
    Ganguly N, Sukai AK, De S (2001) Synth Commun 31:301CrossRefGoogle Scholar
  20. 20.
    Zhou Y, Chu K, Zhen H, Fang Y, Yao C (2013) Spectrochim Acta Part A 106:197CrossRefGoogle Scholar
  21. 21.
    Nishizono N, Oda K, Ohno K, Minami M, Machida M (2001) Heterocycles 55:1897CrossRefGoogle Scholar
  22. 22.
    Prasanna B, Kavitha S (2015) Heteroletters 5:53Google Scholar
  23. 23.
    Dean FM, Park BK (1976) J Chem Soc Perkin Trans 1:1260CrossRefGoogle Scholar
  24. 24.
    Dauzonne D, Royer R (1983) Synthesis 10:836CrossRefGoogle Scholar
  25. 25.
    Gavrilova NA, Semichenko ES, Korotchenko OS, Suboch GA (2008) Russ J Org Chem 44:624CrossRefGoogle Scholar
  26. 26.
    Matos MJ, Santana L, Serra S, Uriarte E, Corda M, Fadda MB, Era B, Fais A (2012) J Pharm Pharmacol 64:742CrossRefGoogle Scholar
  27. 27.
    Sivakumar K, Xie F, Cash BM, Long S, Barnhill HN, Wang Q (2004) Org Lett 6:4603CrossRefGoogle Scholar
  28. 28.
    List B (2002) Tetrahedron 58:5573CrossRefGoogle Scholar
  29. 29.
    Shi CL, Shi DQ, Kim SH, Huang ZB, Ji SJ, Ji M (2008) Tetrahedron 64:2425CrossRefGoogle Scholar
  30. 30.
    Shestakova TS, Khalymbadzha IA, Deev SL, Eltsov OS, Rusinov VL, Shenkarev ZO, Arseniev AS, Chupakhina ON (2011) Russ Chem Bull Int Ed 60:729CrossRefGoogle Scholar
  31. 31.
    Lv H-N, Wang S, Zeng KW, Li J, Guo X-Y, Ferreira D, Zjawiony JK, Tu P-F, Yong J (2015) J Nat Prod 78:279CrossRefGoogle Scholar
  32. 32.
    Rankin KN, Gauld JW, Boyd RJ (2002) J Phys Chem A 106:5155CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Wien 2016

Authors and Affiliations

  1. 1.Department of Chemistry, MMVBanaras Hindu UniversityVaranasiIndia

Personalised recommendations