This paper describes the synthesis of four aryl amide-based macrocycles through the 1 + 1 formation of two 1,2,3-triazole units by click chemistry. Two series of aryl amide-based precursors that bear two azide or acetylene units have been prepared. Intramolecular hydrogen bonding has been utilized to induce them to adopt a U-styled conformation, which remarkably promotes the macrocyclization of two structurally matched precursors.
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http://dx.doi.org/10.1039/b907457k | DOI Listing |
J Am Chem Soc
December 2023
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Owing to the mild generation methods, arynes have been widely used in synthetic chemistry. However, achieving asymmetric organocatalytic reactions with arynes remains a formidable and infrequent challenge, primarily because these neutral and transient species tend to spontaneously quench. To address this issue, a solid-liquid phase-transfer strategy is devised in which the generation speed of arynes could be controlled by the generated fluoride-based chiral phase-transfer catalyst.
View Article and Find Full Text PDFC-C coupling reactions represent a fundamental synthetic methodology widely employed in academic and industrial settings. Herein, we present a report on developing and synthesizing a heterogeneous catalyst that is environmentally compatible and has recycling capabilities. Furthermore, the utilization of this catalyst for C-C coupling reactions was explored.
View Article and Find Full Text PDFPharmaceuticals (Basel)
March 2023
Chemistry Department, College of Sciences, Taibah University, Al-Madinah Al-Munawarah 41477, Saudi Arabia.
COVID-19 infection is now considered one of the leading causes of human death. As an attempt towards the discovery of novel medications for the COVID-19 pandemic, nineteen novel compounds containing 1,2,3-triazole side chains linked to phenylpyrazolone scaffold and terminal lipophilic aryl parts with prominent substituent functionalities were designed and synthesized via a click reaction based on our previous work. The novel compounds were assessed using an in vitro effect on the growth of SARS-CoV-2 virus-infested Vero cells with different compound concentrations: 1 and 10 μM.
View Article and Find Full Text PDFJ Org Chem
July 2022
Showa Pharmaceutical University, 3-3165 Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan.
Amide-based molecular switches had its limitation on structural diversities. In this work, we designed and synthesized a series of pentafluorobenzoyl-based benzanilide compounds. The conformational ratio of these compounds in solution was correlated linearly with Hammett's σ value of the substituent on the anilide ring, reflecting the repulsive interaction between the carbonyl group and the electron-rich aryl group.
View Article and Find Full Text PDFOrg Biomol Chem
February 2022
State Key Laboratory of Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong.
A novel family of indole-amide-based phosphine ligands was designed and synthesized. The Pd/InAm-phos (L1) catalytic system exhibited excellent efficiency in the Suzuki-Miyaura cross-coupling of sterically hindered (hetero)aryl chlorides to synthesize tri--substituted biaryls. Excellent product yields were obtained in a short reaction time (, 10 min), and a Pd catalyst loading down to 50 ppm was also achieved.
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