Synthesis of 1,4-Diazacycles by Hydrogen Borrowing
Synthesis of 1,4-Diazacycles by Hydrogen Borrowing
复制标题
借氢合成1,4-二氮杂环化合物
DOI：
10.1021/acs.orglett.3c00468
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发表时间：
2023
期刊：
影响因子：
5.2
通讯作者：
Williams, Travis J.
中科院分区：
文献类型：
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作者：
Nalikezhathu, Anju;Tam, Adriane;Cherepakhin, Valeriy;Do, Van K.;Williams, Travis J.
我们报道了通过二醇-二胺偶联合成1,4-二氮环的方法，这种方法是用（吡啶基）膦连接钌（II）催化剂(1)唯一实现的。该反应可以利用两个连续的n -烷基化或中间的互变异构化途径生成哌嗪和二氮杂烷；通过催化途径通常无法获得二氮杂环类化合物。我们的身体条件可以耐受与关键药物平台相关的不同胺和醇。结果表明，合成环利嗪和同氯环利嗪的产率分别为91%和67%。
We report the syntheses of 1,4-diazacycles by diol–diamine coupling, uniquely made possible with a (pyridyl)phosphine-ligated ruthenium(II) catalyst (1). The reactions can exploit either two sequentialN-alkylations or an intermediate tautomerization pathway to yield piperazines and diazepanes; diazepanes are generally inaccessible by catalytic routes. Our conditions tolerate different amines and alcohols that are relevant to key medicinal platforms. We show the syntheses of the drugs cyclizine and homochlorcyclizine in 91% and 67% yields, respectively.