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Synthesis and characterization of novel naphtodiazacrown macrocyclic Shiff bases

Synthesis and characterization of novel naphtodiazacrown macrocyclic Shiff bases Andrea Dandića, Marija Paurevića, Martina Šrajer Gajdošika and Tomislav Balića a Department of Chemistry, Josip Juraj Strossmayer University of Osijek, Cara Hadrijana 8/A, 31000 Osijek, Croatia Macrocyclic ligands are known to bind metal ions selectively and are thus employed as carriers in metal selective extraction, phase transfer catalyses, membrane transport and other related processes.[1] Over the last couple of decades oxa-aza macrocycles have been extensively studied [2 for that purpose and as well as a novel chemical sensors, pharmaceuticals and liquid crystals [3. There are three major synthetic strategies for preparation of oxa-aza macrocycles ; (i) template synthesis, (ii) high-dilution technique, and (iii) cyclocondenzation reaction of poly-amine and poly-aldehyde precursors resulting in a formation of poly-imine compounds [4. Prior to this study we have prepared various dialdehyde precursors by reaction of 2 equiv. of 2-hydroxy-1- naphtaldehyde and 1 equiv. of α, ω-dibrominated aliphatic hydrocarbons (1, 4-dibromobutane, 1, 5- dibromopentane and 1, 6-dibromohexane). All prepared dialdehydes in reactions with m- phenylenediamine resulted in the formation of novel naphtodiazacrown macrocyclic compounds. (Scheme 1.) The characterization of compounds was done by NMR and IR spectroscopy and suitable crystals of all prepared compounds were used for single crystal X-ray analysis. Scheme 1.Preparation of macrocyclic Shiff bases from dialdehydes [1] D.S. Kumar, V. Alexander, Inorg.Chim.Acta, 238 (1995) 63-71. [2] H. Adams, R. Bastida, D.E. Fenton, A. Macias, S.E. Spey, L. Valencia, J. Chem. Soc. Dalt. Trans. 23 (1999) 4131–4137. [3] J.Q. Zhang, C.Y. Jia, Chin. J. Org. Chem. 30 (2010) 1142–1155. [4] L. Tei, A.J. Blake, A. Bencini, B. Valtancoli, C. Wilson, M. Schröder, J. Chem. Soc. Dalt. Trans. 22 (2000) 4122–4129.

Macrocycles, Shiff bases, cyclocondenzation reactions

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