Synthesis of new aza- and thia-crown ethers and their metal ion templates synthesis as model case study

Abstract

Four new thia- and four new aza- crown ethers were synthesized using the reaction of ethylene glycols ditosylated with 1,1́-(2,2́- dihydroxynaphthyl)sulfide (DNS) and 2,6-bis(3- hydroxyphenyl)-4-phenylpyridine in acetonitrile as solvent in the presence of bases (LiOH, NaOH, KOH and Cs 2CO3). In the synthesis of macrocycles based on DNS, the template effects of alkaline metal ions; Li+, Na+, K+ and Cs+ on the reaction yields were investigated. Sodium template generally was more effective for the synthesis of all four macrocycles. Relatively, good yields of 15- and 18-membered macrocycles were obtained in the presence of all kinds of applied cations. K+ Cation was more effective template ion than Na+ in the formation of 18-membered macrocycles due to their larger cavity size compared to the 15-membered cycles. The structures of macrocycles were confirmed by CHN/O analysis, IR, 1H NMR, 13C NMR and mass spectrometry. © ARKAT-USA, Inc.