Modifications of 7-hydroxy- 3-(benzothiazol-2-yl)coumarin
Keywords:7-hydroxy-3-benzothiazolylcoumarin, aminomethylation, formylation, homoisoflavones, recyclization
This paper is devoted to 7-hydroxy-3-(benzothiazol-2-yl)coumarin modifications using the dimethylaminomethyl and formyl groups introduced in 8 position, useful for further structural transformations. Derivatives of the dihydrooxazinocoumarin system were obtained by aminomethylation of 7-hydroxy-3-(benzothiazol-2-yl) coumarin under the classical Mannich reaction conditions using an excess of formalin. Starting from 8-dialkylaminomethyl-7-hydroxy-3-(benzothiazol-2-yl)coumarin the corresponding Mannich bases were synthesized by transamination with benzylamines, homoisoflavone derivatives were obtained as a result of the interaction with o-hydroxyarene enaminoketones and 3-(benzothiazol-2-yl)-7-hydroxy-8-formylcoumarin was obtained under the Duff reaction conditions. The latter in the reaction with 4-nitrophenacyl bromide formed the furo[2,3-h]coumarin system derivative. The recyclizations of 3-(benzothiazol-2-yl)-7-hydroxy- 8-(4-oxo-4H-3-chromenylmethyl)-2H-2-chromenone under the action of binucleophiles were studied.
Chao, R. Y., Ding, M. F., Chen, J. Y., Lee, C. C. & Lin, S. T. (2010). Preparation and characterization of substituted 3-benzothiazol-2-ylcoumarins. J. Chin. Chem. Soc., 57, No. 2, pp. 213-221. https://doi.org/10.1002/jccs.201000033
Zhang, H., Li, M., Feng, W. & Feng, G. (2017). Rapid and selective detection of selenocysteine with a known readily available colorimetric and fluorescent turn-on probe. Dyes and Pigments, 149, pp. 475-480. https://doi.org/10.1016/j.dyepig.2017.10.031
Wang, C., Xu, F., Niu, Y., Wu, Y., Sun, Y., Peng, Y., Liang, L. & Xu, P. (2013). Synthesis and biological eva lua-tions of 3-benzothiazol-2-yl coumarin derivatives as MEK1 inhibitors. Letters in drug design and discovery, 10, No. 8, pp. 727-732. https://doi.org/10.1691/ph.2019.9664
Khilya, O. V., Frasinyuk, M. S., Turov, A. V. & Khilya, V. P. (2001). Chemistry of 3-hetarylcoumarins. 1. 3-(2-benzazolyl)-coumarins. Chem. Het. Compd. 37, No. 8, pp. 1029-1037. https://doi.org/10.1023/A:1012704121345
Wolfbeis, O. S, Koller, E. & Hochmuth, P. (1985). The unusually strong effect of a 4-cyano group upon electronic spectra and dissociation constants of 3-substituted 7-hydroxycoumarin. Bull. Chem. Soc. Jpn., 58, No. 2, pp. 731-734. https://doi.org/10.1246/bcsj.58.731
Khoobi, M., Ramazani. A., Foroumadi, A. R., Hamadi, H., Hojjati, Z. & Shafiee, A. (2011). Efficient micro-wave-assisted synthesis of 3-benzothiazolo and 3-benzothiazolino coumarin derivatives catalyzed by hetero-poly acids. J. Iran. Chem. Soc., 8, No. 4, pp. 1036-1042. https://doi.org/10.1007/BF03246560
Roubinet, B., Renard, P. -Y. & Romieu, A. (2014). New insights into the water-solubilization of thiol-sensitive fluorogenic probes based on long-wavelength 7-hydroxycoumarin scaffolds. Dyes and Pigments, 110, pp. 270-284. https://doi.org/10.1016/j.dyepig.2014.02.004
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