A click chemistry approach for the synthesis of macrocycles from aryl amide-based precursors directed by hydrogen bonding.
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.
Zhu
Yuan-Yuan
YY
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, 345 Lingling Lu, Shanghai, 200032, China.
Wang
Gui-Tao
GT
Li
Zhan-Ting
ZT
D000577:Amides / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D003500:Cyclization; D006860:Hydrogen Bonding; D015394:Molecular Structure; D055672:Static Electricity
D000577:Amides; D001386:Azides