O-Alkylation Redirected Condensation of 5-Hydroxy-1,2-oxazine-6-ones with Primary Amines for Synthesis of 5-Hydroxyiminopyridine-2,6(1H,3H)-diones,ChemistrySelect

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O-Alkylation Redirected Condensation of 5-Hydroxy-1,2-oxazine-6-ones with Primary Amines for Synthesis of 5-Hydroxyiminopyridine-2,6(1H,3H)-diones
ChemistrySelect ( IF 1.9 ) Pub Date : 2021-09-08 , DOI: 10.1002/slct.202102295
Alexey V. Nizovtsev ₁ , Anatolii I. Sokolov _{1,

2} , Alexander Yu. Smirnov _{1,

2} , Andrey A. Mikhaylov ₁ , Ivan N. Myasnyanko _{1,

2} , Olga A. Belozerova ₁ , Nadezhda S. Baleeva _{1,

2} , Liliia Usmanova ₁ , Mikhail S. Baranov _{1,

2}

Affiliation

Herein we report a short and general protocol for synthesis of potentially biologically active pyridine-2,6-diones. The approach is based on the redirection of the condensation of the intermediates of Dornow reaction – 5-hydroxy-1,2-oxazine-6-ones with primary amines by their prior O-alkylation. Such manipulation blocks their transformation into isoxazoles and allows one to obtain a library of 30+ previously undescribed 5-alkoxy-3-(hydroxyimino)-4-aryl-pyridine-2,6(1H,3H)-dione derivatives in 37–89 % yields.

中文翻译：

5-羟基-1,2-恶嗪-6-酮与伯胺的O-烷基化重定向缩合合成5-羟基亚氨基吡啶-2,6(1H,3H)-二酮

在此，我们报告了一个简短的通用协议，用于合成具有潜在生物活性的 pyridine-2,6-diones。该方法基于 Dornow 反应中间体 - 5-羟基-1,2-恶嗪-6-酮与伯胺的缩合重定向，通过它们之前的O-烷基化。这种操纵块它们转化为异恶唑并允许获得的30+库以前未描述5-烷氧基-3-（羟基亚氨基）-4-芳基吡啶-2,6-（1 ħ，3 ħ） -二酮衍生物在37 –89% 的产量。

更新日期：2021-09-09

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