硼酸三甲酯辅助半姜黄素和邻苯二胺合成1,5-二氢二氮卓类药物

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-07-29 DOI:10.1016/j.tetlet.2025.155771

Ivan A. Kochnev, Elizaveta M. Gomzikova, Nikolay A. Tverdokhlebov, Alexey Y. Barkov

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引用次数: 0

摘要

在这项工作中，我们证明了半姜黄素可切换转化为1,5-苯二氮卓类或1,5-二氢苯二氮卓类。这些化合物的合成是基于硼活化在DCM中的半姜黄素上添加邻苯二胺。这种方便和简单的方法可以得到功能化的1,5-二氢苯二氮卓类药物，收率高达65%。验证了硼活化剂的作用。以乙酸为溶剂改变了化学选择性，加成的邻苯二胺和1,5-苯二氮卓类化合物收率可达40%。此外，1,5-二氢苯二氮卓类药物在酸性条件下再循环成1,5-苯二氮卓类药物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Trimethyl borate assisted chemoselective synthesis 1,5-dihydrodiazepines from hemicurcuminoids and o-phenylenediamines

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Trimethyl borate assisted chemoselective synthesis 1,5-dihydrodiazepines from hemicurcuminoids and o-phenylenediamines

In this work, we demonstrate the switchable transformation of hemicurcuminoids to 1,5-benzodiazepines or 1,5-dihydrobenzodiazepines. The synthesis of these compounds was based on the boron-activated addition of o-phenylenediamines to hemicurcuminoids in DCM. This convenient and simple protocol allows obtaining functionalized 1,5-dihydrobenzodiazepines with yields up to 65 %. The effect of boron activator was demonstrated. The use of acetic acid as a solvent changes the chemoselectivity of addition of o-phenylenediamine and 1,5-benzodiazepines are formed up to 40 % yield. Moreover, 1,5-dihydrobenzodiazepines undergoes recyclization into 1,5-benzodiazepines under acidic conditions.

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.