Coumarin phthalonitriles: Synthesis and cation binding properties
DOI:
https://doi.org/10.24297/jac.v11i4.6695Keywords:
Synthesis of coumarin phtalonitriles, Stability constants, UV spectrophotometry, Cation binding propertiesAbstract
Coumarin possess a number of biological activities like anticoagulant, antimicrobial, anti-inflammatory, analgesic,antioxidant, anticancer, antiviral, antimalarial etc. Coumarin belongs to a group as benzopyrones, which consists of a benzene ring joined to a pyrone nucleus. In this work, new coumarin phtalonitriles derivatives were synthesized and characterized via spectroscopic techniques IR, 1H NMR, 13C NMR, mass spectra and elemental analysis.The synthesis of coumarin phtalonitriles resulting from a nucleophilic aromatic substitution reaction between 4-nitrophtalonitrile and coumarins derivatives. The complexing properties of the coumarin derivatives toward alkali metal, alkaline earth metal, some transition metals and some heavy metal cations have been investigated in acetonitrile by means of UV spectrophotometry absorption and conductivity methods. Thus, the stoichiometry of the complexes formed and their stability constants were determined
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References
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[3] For a review, see: L. Santana, E. Uriarte, F. Roleira, N. Milhazes and F. Borges, Curr. Med. Chem., 2004, 11, 3239.
[4] For selected examples, see: (a) V. K. Ahluwalia, R. Adhikari and R. P. Singh, Heterocycles, 1986, 24, 1919; (b) K. Kobayashi, K. Sakashita, H. Akamatsu, K. Tanaka, M. Uchida, T. Uneda, T. Kitamura, O. Morikawa and H. Konishi, Heterocycles, 1999, 51, 2881; (c) S. Tollari, G. Palmisano, S. Cenini, G. Cravotto, G. B. Giovenzana and A. Penoni, Synthesis, 2001, 735; (d) Y. R. Lee, B. S. Kim and H. C. Wang, Tetrahedron, 1998, 54, 12215; (e) Y. R. Lee, J. Y. Suk and B. S. Kim, Tetrahedron Lett., 1999, 40, 6603; (f) F. Risitano, G. Grassi, F. Foti and C. Bilardo, Tetrahedron Lett., 2001, 42, 3503; (g) V. Nair, R. S. Menon, A. U. Vinod and S. Viji, Tetrahedron Lett., 2002, 43, 2293; (h) C. C. Li, Z. X. Xie, Y. D. Zhang, J. H. Chen and Z. Yang, J. Org. Chem., 2003, 68, 8500; (i) R. V. Rozh kov and R. C. Larock, Org. Lett., 2003, 5, 797; (j) N. Al-Maharik and N. P. Botting, Tetrahedron, 2004, 60, 1637; (k) T. Yao, D. Yueand R. C. Larock, J. Org. Chem., 2005, 70, 9985; (l) G. Raffa, M. Rusch, G. Balme and N. Monteiro, Org. Lett., 2009, 11, 5254.
[5] (a) G. Cheng and Y. Hu, Chem. Commun., 2007, 3285; (b) G. Cheng and Y. Hu, J. Org. Chem., 2008, 73, 4732; (c) W. Huang, J. Wang, Q. Shen and X. Zhou, Tetrahedron, 2007, 63, 11636; (d) V. Cadierno, J. D´ıez, J. Gimeno and N. Nebra, J. Org. Chem., 2008, 73, 5852; (e) D. Conreaux, S. Belot, P. Desbordes, N. Monteiro and G. Balme, J. Org. Chem., 2008, 73, 8619; (f) Y. R. Lee, M. W. Byun and B. S. Kim, Bull. Korean Chem. Soc., 1998, 19, 1080
[6] L. Chen and M.-H. Xu, Adv. Synth. Catal., 2009, 351, 2005.
[7] (a) F. Alonso, I. P. Beletskaya and M. Yus, Chem. Rev., 2004, 104, 3079; (b) N. T. Patil, L. M. Lutete, H. Wu, N. K. Pahadi, I. D. Gridnev and Y. Yamamoto, J. Org. Chem., 2006, 71, 4270; (c) S. Seo, X. Yu and T. J. Marks, J. Am. Chem. Soc., 2009, 131, 263 and references therein.
[8] (a) L. Zhang, T. Meng, R. Fan and J. Wu, J. Org. Chem., 2007, 72, 7279; (b) Z. Wang, B. Wang and J. Wu, J. Comb. Chem., 2007, 9, 811.
[9] (a) K. Sonogashira, In Handbook of Organopalladium Chemistry for Organic SynthesisE. Negishi, Ed.; Wiley: New York, 2002, pp 493–529; (b) R. Chinchilla and C. Najera, ´ Chem. Rev., 2007, 107, 874.
[10] (a) E. Negishi, Acc. Chem. Res., 1982, 15, 340; (b) E. Negishi, C. Xu, In Handbook of Organopalladium Chemistry for Organic SynthesisE. Negishi, Ed.; Wiley: New York, 2002, pp 531–549; (c) E. Negishi, Bull. Chem. Soc. Jpn., 2007, 80, 233.
[11] (a) E. Negeshi and L. Anastasia, Chem. Rev., 2003, 103, 1979; (b) L Anastasia and E Negishi, Org. Lett., 2001, 3, 3111; (c) E. Negishi, M. Qian, F. Zeng, L. Anastasia and D. Babinski, Org. Lett., 2003, 5, 1597; (d) J. Shi, X. Zeng and E. Negishi, Org. Lett., 2003, 5, 1825; (e) I. J. S. Fairlamb, F. J. Lu and J. P. Schmidt, Synthesis, 2003, 2564
[12]. Abidi R., Baklouti L., Harrowfield J. M., Sobolev A. N., Vicens J. and White A. H. Alkali metal ion complexes of functionalised calixarenes–competition between pendent arm and anion bonding to sodium, Org. Biomol. Chem., 2003,1, 3144–3146.
[13]. Baklouti L., Cherif J., Abidi R., Arnaud-Neu F., Harrowfield J. and Vicens J. Synthesis and binding properties of calix[4]arenes with [2+2']mixed ligating functional groups, Org. Biomol. Chem., 2004,2, 2786–2792.
[14]. Naouali O., Frija R., Elgabsi W., Hamdi N. and Baklouti, L. Coumarin derivatives: Synthesis and cation binding properties, Med. J. Chem.,2014, 3, 1057-1065
[15]. Ben Othman, A.; Baklouti, L.; Abidi, R.; Vicens, J., Cation binding properties by ammonium glycolic and pyridinium amidocalix[4]arenes, Lett. Org. Chem.,2007, 4, 339-343.
[16]. Thabet W., Baklouti L., Zieba R. and Parola S. Cation binding by thiacalixthianthrenes, J. Inclusion. Phenom., 2012,73, 135-139.
17. Naouali O., Soleiman H. and Baklouti L. Cation binding by some pyranopyridothiazolederivatives, Eur. J. Chem., 2014,5, 339-342.
[18]. Naouali O., Hamdi A., Abderrahim R. and Baklouti L. Inclusion properties of 3-amino-5-methypyrazole towards some metal cations, Phy. Chem. An Ind. J.,2014, 9, 119-123.
[19]. Naouali O., Boubakri L., Hamdi N. and Baklouti, L. Cation Binding properties of some coumarin derivatives in acetonitrile, Med Asian J. of Adv. Basic Sci.: 2015,3, 186-193
[20]. Sillen, G.; Warnquist, B.; Ark. Kemi.,1968, 31, 377-390 .
[21]. Ben Othman A., Abidi R., Baklouti, L. and Vicens J. Extraction and complexation of alkali and alkaline earth cations by 1,3-bis(aminoalkylamido)calix[4]arenes; Org. Chem. An Ind. J.,2005, 1, 38-43
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2015-03-09
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Medyouni, R., Naouali, O., HAMDI, N., & Baklouti, L. (2015). Coumarin phthalonitriles: Synthesis and cation binding properties. JOURNAL OF ADVANCES IN CHEMISTRY, 11(4), 3512–3518. https://doi.org/10.24297/jac.v11i4.6695
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