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Published on: February 7, 2019
Water-Phase Synthesis of 2,5-Methanobenzo[d][1,3,6]oxadiazocine with Low Catalyst Loading
Yueyue Fan1, Jun Tan1, Qiuyan Wang2
1School of Pharmaceutical Sciences, Capital Medical University, Beijing100069, China.
Abstract:
Herein, we report a novel strategy to construct bridged benzo[1,3,6]oxadiazocine scaffold from γ-hydroxy enals and o-phenylenediamine, a transformation that diverges from the conventional benzimidazole formation via aldehyde 1,2-addition. This protocol features unprecedented reactivity, green conditions (water solvent, 1 mol % catalyst, room temperature), simple operations, broad substrate scope, and versatile product derivatization, providing a practical and sustainable route to three-dimensional scaffolds of potential value in medicinal chemistry.
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