A click chemistry approach for the synthesis of macrocycles from aryl amide-based precursors directed by hydrogen bonding.

Org Biomol Chem

State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, 345 Lingling Lu, Shanghai, 200032, China.

Published: August 2009

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/b907457kDOI Listing

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