Anion‐Templated Syntheses of Pseudopeptidic Macrocycles

Abstract

A very welcome guest: The terephthalate anion efficiently templates the selective assembly of a tetraimino dianion host–guest complex, which can be reduced to the final [2+2] pseudopeptidic macrocycle (see scheme; O red, blue N).

Organogel–quantum dots hybrid materials displaying fluorescence sensitivity and structural stability towards nitric oxide

“…In this context, pseudopeptidic compounds are good receptors of anions due to the coordination properties of the amide groups [2,3]. For this purpose, the preorganization provided by macrocyclic structures is important, and the preparation of such structures from C 2 pseudopeptidic bis(amidoamines) has been investigated in detail in our research group [4][5][6][7]. Previous studies focused on compounds such as 1 (Scheme 1) [4].…”

Synthesis and Evaluation of Pseudopeptidic Fluorescence pH Probes for Acidic Cellular Organelles: In Vivo Monitoring of Bacterial Phagocytosis by Multiparametric Flow Cytometry

“…templates, as typically described in the synthesis of large macrocycles. [45,47] It has been demonstrated that a combination of solvophobic effects and the occurrence of preorganization of the intermediates, assisted by intramolecular hydrogen-bonding, explain such good yields. [40] The open-chain derivatives were synthesized in a similar way but by using the corresponding alkaneamines (Scheme 3).…”

“…[40][41][42][43][44][45] The probes are of three types: Macrocyclic bis-aminoamides 1-7, openchain bis-aminoamides 8 and 9, and mono-aminoamides 10-12. As can be seen in Scheme 1, the differences between these compounds comprise slight variations in the chemical nature of the building blocks employed for their synthesis, such that either valine or phenylglycine have been used as well as different polymethylene bridges with n = 2, 3, 4, 5, 6 or 8 units.…”

Recent Developments in Chiral Polynitrogenated Synthetic Receptors for Anions

“…Pseudopeptidic macrocycles bearing both amine and amide functional groups have been also reported by Luis et al [57][58][59][60][61][62] The key step for the synthesis of these compounds is the macrocyclization reaction, which is favored by the fold- . (13).…”

“…Taking advantage of the amide-anion strong interaction, we envisioned to use an anion to produce the necessary preorganization in the case of the more flexible derivatives (49a,b) [62]. Taking advantage of the amide-anion strong interaction, we envisioned to use an anion to produce the necessary preorganization in the case of the more flexible derivatives (49a,b) [62].…”