Tethered aza-Wacker cyclization reactions with unusual N-alkoxy carbamates

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-05-17 DOI:10.1016/j.tet.2025.134730

Appasaheb K. Nirpal , Dnyaneshwar A. Gorve , Raju Silver , Steven P. Kelley , Shyam Sathyamoorthi

引用次数: 0

Abstract

Substrates with N-alkoxy carbamate “heads” and olefin “tails” can be productively cyclized into 1,3-oxazinan-2-one products bearing pendant alkenes. Our reaction protocol is operationally simple and involves heating the substrate with a mixture of Pd (II) and Cu (II) salts in CH₃CN under 1 atm of O₂. We hypothesize that an aza-Wacker mechanism is operative, based on prior art and our own experience with this reaction class. An array of substrates is compatible, and the heterocyclic products are amenable to further transformations.

查看原文本刊更多论文

不寻常的n -烷氧基氨基甲酸酯系链aza-Wacker环化反应

具有n-氨基甲酸酯“头”和烯烃“尾”的底物可以有效地环化成带有垂链烯烃的1,3-恶氮杂烷-2- 1产物。我们的反应方案操作简单，只需将Pd （II）和Cu （II）盐的混合物放在CH3CN中，在1atm的O2下加热底物。基于现有技术和我们自己对这类反应的经验，我们假设aza-Wacker机制是有效的。一组底物是相容的，并且杂环产物可以进一步转化。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.