• Vidoslav Dekić Faculty of Sciences, University of Priština - Kosovska Mitrovica, Kosovska Mitrovica, Serbia
  • Niko Radulović Department of Chemistry, Faculty of Sciences and Mathematics, University of Niš, Niš, Serbia
  • Milenko Ristić Faculty of Sciences, University of Priština - Kosovska Mitrovica, Kosovska Mitrovica, Serbia
  • Biljana Dekić Faculty of Sciences, University of Priština - Kosovska Mitrovica, Kosovska Mitrovica, Serbia
  • Novica Ristić Faculty of Sciences, University of Priština - Kosovska Mitrovica, Kosovska Mitrovica, Serbia
Keywords: Coumarins, Synthesis, Spectral analysis, 1H NMR, 13C NMR, 2D NMR


This research involves the reaction of 4-chloro-3-nitrocoumarin and (4-methoxyphenyl)methanamine, whereby a novel coumarin derivative 4-[(4-methoxybenzyl) amino]-3-nitro-2H-chromen-2-one was obtained in good yield. The reaction was carried out in ethyl acetate, in the presence of triethylamine. Also, a detailed spectral analysis of a new coumarin derivative is presented. Resonance assignment was achieved using one- (1H NMR and 13C NMR) and two-dimensional NMR techniques (1H-1H-COSY, NOESY, HSQC, and HMBC). The NOESY correlations of protons from arylamino substituent and coumarin core indicate their spatial orientation.


Barry, R. D. 1964. Isocoumarins. Developments science 1950. Chemical Reviews, 64(3), pp. 229-260. doi: 10.1021/cr60229a002

Dekić, V., Dekić, B., & Radulović, N. 2013. 1H and 13C NMR spectral assignments of an amino acid-coumarin hybrid. Facta Universitatis Series: Physics, Chemistry and Technology, 11(3), pp. 101-107. doi: 10.2298/fupct1301101d

Dekić, V., Radulović, N., Vukićević, R., Dekić, B., Skropeta, D., & Palić, R. 2010. Complete assignment of the 1H and 13C NMR spectra of antimicrobial 4-arylamino-3-nitrocoumarin derivatives. Magnetic Resonance in Chemistry, 48(11), pp. 896-902. doi: 10.1002/mrc.2681

Finn, G. J., Creaven, B., & Egan, D. A. 2001. Study of the in vitro cytotoxic potential of natural and synthetic coumarin derivatives using human normal and neoplastic skin cell lines. Melanoma Research, 11(5), pp. 461-467. doi: 10.1097/00008390-200110000-00004

Jiménez-Orozco, F. A., Molina-Guarneros, J. A., Mendoza-Patiño N., León-Cedeño, F., Flores-Pérez, B., Santos-Santos, E., & Mandoki, J. J. 1999. Cytostatic activity of coumarin metabolites and derivatives in the B16-F10 murine melanoma cell line. Melanoma Research, 9(3), pp. 243-247. doi: 10.1097/00008390-199906000-00005

Jung, K., Park, Y. J., & Ryu, J. S. 2008. Scandium(III) Triflate–Catalyzed Coumarin Synthesis. Synthetic Communications, 38(24), pp. 4395-4406. doi: 10.1080/00397910802369513

Kaljaj, V., Trkovnik M., & Stefanović-Kaljaj, L. 1987. Syntheses of new heterocyclocoumarins starting with 3-cyano-4-chlorocoumarin. Journal of the Serbian Chemical Society, 52(4), pp. 183-185.

Li, X., Zhao, Y. X., Wang, T., Shi, M. Q., & Wu, F. P. 2007. Coumarin derivatives with enhanced two-photon absorption cross-sections. Dyes Pigments, 74(1), pp. 108-112. doi: 10.1016/j.dyepig.2006.01.020

Melavanki, R. M., Kusanur, R. A., Kulakarni, M. V., & Kadadevarmath, J. S. 2008. Role of solvent polarity on the fluorescence quenching of newly synthesized 7,8-benzo-4-azidomethyl coumarin by aniline in benzene-acetonitrile mixtures. Journal of Luminescence, 128(4), pp. 573-577. doi: 10.1016/j.jlumin.2007.08.013

Murray, R. D. H. 1989. Coumarins. Natural Product Reports, 6, pp. 591-624.

Murray, R. D. H., Mendez, J., & Brown, S. A. (1982) The Natural Coumarins: Occurrence, Chemistry and Biochemistry. New York: Wiley & Sons.

O’Kennedy, R., & Thornes, R. D. (1997) Coumarins - Biology, Applications and Mode of Action. Chichester: John Wiley & Sons.

Turki, H., Abid, S., Fery-Forgues, S., & El Gharbi, R. 2007. Optical properties of new fluorescent iminocoumarins: Part 1. Dyes Pigments, 73(3), pp. 311-316. doi: 10.1016/j.dyepig.2006.01.001

Yu, T., Zhang, P., Zhao, Y., Zhang, H., Meng, J., & Fan, D. 2009. Synthesis and photoluminescent properties of two novel tripodal compounds containing coumarin moieties. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 73(1), 168-173. doi: 10.1016/j.saa.2009.02.013

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