Facile synthesis of mono and dibenzo N,N'‐disubstituted diaza 18‐crown‐6 derivatives

Abstract

This study represents a facile synthesis of building blocks (1–3) of crown ethers and amine precoursers (4a‐d). The study also involves synthesis of mono and dibenzo N, N‐disubstituted diaza 18‐crown‐6 derivatives with high yield without chromatographic purification and high vacuum distillation. The complex ability of host the ethers was evaluated in terms of structural modification.

Enantioselective recognition of ammonium perchlorate salts by optically active monoaza‐15‐crown‐5 ethers

“…In the reaction, two catalyts were used, diethylamine hydrochloride and piperidine hydrochloride, but the yield of the product was similar. 18 Tosylates 5 and 6 were prepared according to reported procedures. 18,19 The chiral macrocycles 1 and 2 were prepared in 65% and 69% yields, respectively, as shown in Scheme 2.…”

“…18 Tosylates 5 and 6 were prepared according to reported procedures. 18,19 The chiral macrocycles 1 and 2 were prepared in 65% and 69% yields, respectively, as shown in Scheme 2. Crown ethers 1 and 2 were obtained directly as their NaClO 4 ÁH 2 O complexes.…”

Synthesis, Structural Characterization and Complexation Properties of the First “Crowned” Dipyrrolylquinoxalines

“…Thin-layer chromatography (TLC) analyses were performed on silica gel 60 F 254 (200 µm thickness) or aluminum oxide 60 F 254 (200 µm thickness) as appropriate, with 5% MeOH in CH 2 Cl 2 as the eluent. 1,2-Bis[2-(p-tosyloxy)ethoxy]benzene (5), [11] 1,2-bis(1H-pyrrol-2-yl)ethanedione (20), [8a] and 2,3-bis(1H-pyrrol-2-yl)quinoxaline (22) [8a] were prepared as previously reported.…”

“…They were obtained by adapting the procedure of Okahara and co-workers that was developed to prepare mono-azacrown diethyl ethers (Scheme 1). [10] Specifically, 1,2-bis[2-(p-tosyloxy)ethoxy]benzene (5) [11] was reacted with azadiol 6 or diethanolamine 7 in a tert-butyl alcohol/ dioxane mixture in the presence of potassium tert-butoxide to give benzo-aza-18-crown-6 10 (26%) and benzo-15-crown-5 11 (16%), respectively. [12] To the best of our knowledge, this is the first time that the synthesis and full characterization of 10 has been described.…”

Synthesis and spectroscopic characterization of transition metal complexes of a 12-membered tetraaza [N4] macrocyclic ligand and their biological activity

“…Macrocyclic compounds and their derivatives are interesting ligand systems because they are good hosts for metal anions, neutral molecules and organic cation guests [1][2][3][4]. The family of complexes with aza-macrocyclic ligands has remained a focus of scientific attention for many decades [5,6].…”