SYNTHESIS AND COMPLETE NMR SPECTRAL ASSIGNMENTS OF NEW BENZYLAMINO COUMARIN DERIVATIVE

  • Vidoslav Dekić Faculty of Sciences, University in 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 in Priština - Kosovska Mitrovica, Kosovska Mitrovica, Serbia
  • Biljana Dekić Faculty of Sciences, University in Priština - Kosovska Mitrovica, Kosovska Mitrovica, Serbia
  • Novica Ristić Faculty of Sciences, University in Priština - Kosovska Mitrovica, Kosovska Mitrovica, Serbia
Keywords: Coumarins, Synthesis, Spectral analysis, 1H NMR, 13C NMR, 2D NMR

Abstract


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.

References

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

Published
2020/06/17
Section
Original Scientific Paper