New ten macrocycles 5a-cand e-k and one cryptand 5d were synthesized by the reaction of diamine compounds
4a-k with N,N'-bis(2-chloroacetamido)-2,6-diaminopyridine (BCDP) 3 in the presence of K2CO3 and KI in good to high
yields. Also the template effects of cations such as Na+, K+, K+/KI and Cs+ on the reaction yields for macrocycles (4a-c and
I, k) were investigated. In this study it is found that size matching and template effect of K+ with KI as catalyst are most
suitable for macrocyclization process. The structures of macrocycles and cryptand were confirmed by IR, 1H NMR, 13C
NMR and Mass spectroscopies. Additionally, computational 1H and 13C NMR parameters of cryptand 5d were obtained
using density functional theory (DFT) at B3LYP/6-31G* level. The calculated chemical shifts were found to be in agreement
with experimental data.
Keywords: Aza macrocycle, cryptand, 2, 6-Diaminopyridine, template effect, computational NMR.
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