Abstract
A simple one-pot synthesis of amidopiperazinophanes with a combination of electron-deficient amide groups and electron-rich alkyne and piperazine functionalities has been achieved by using multicomponent reaction (MCR) methodology with the Mannich reaction. Herein, we demonstrate the synthesis of macrocyclic amide structures in good yields. These macrocycles, with electron donor/acceptor sites, are versatile molecules for host–guest and binding.
Highlights
Our aim was to extend the study to various amidopiperazines with different heteroatoms and aromatic monocyclic spacer units
We reported cyclophanes with intra-annular amide functionalities for selective ion transportation[14] as well as for the development of bioactive compounds.[15]
Our observations suggest that these amide cyclophanes could be potential candidates for pharmaceutical applications
Summary
This synthetic approach has advantages, including ease of manipulation, simple purification and intrinsic atom economy. To achieve target amide macrocycles 1–12, precyclophanes 13–18 with terminal bisalkynes were used as the main building blocks with S-propargyloxy-2-aminothiophenol 193b as the other starting precursor. In this context, our initial aim focused on the synthesis of the precyclophanes using various aromatic diacid chlorides including phthaloyl chloride 20, isophthaloyl chloride 21, terephthaloyl chloride 22, pyridine-2,6-dicarboxylic acid chloride 23, 5-hydroxyisophthaloyl dichloride 24, and thiophene-2,5-dicarbonyl dichloride 25. The aromatic diacid chlorides 20–25 were synthesized according to the reported procedure.[22]
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