Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7'-cyclopenta[d]pyrimidin]-4-one core

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-06-14 DOI:10.1016/j.tet.2025.134791

Nikolai A. Arutiunov, Stanislav V. Shcherbakov, Daria A. Shtal, Maksim O. Shcheglov, Kirill V. Tolstov, Daria I. Murashkina, Nicolai A. Aksenov, Alexander V. Aksenov

引用次数: 0

Abstract

Novel iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols leading to spiro[cyclohexa[2,5]diene-1,7'-cyclopenta[d]pyrimidin]-4-one core was developed. This sequence, based commercially available reagents starts with acid-catalyzed electrophilic alkylation of phenols with 5-bromopyrimidine. Subsequently, an oxidation, palladium-catalyzed Sonogashira cross-coupling reaction and electrophilic spirocyclization, allowed to target product with good yields and simple synthetic protocols.

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亲电性碘离子介导的4-（5-（芳基乙基）嘧啶-4-基）苯酚的螺旋环化反应生成螺旋[环己[2,5]二烯-1,7'-环五[d]嘧啶]-4- 1核

研究了新型碘离子介导的4-（5-（芳基乙基）嘧啶-4-基）苯酚的螺旋环化反应，得到螺旋[环己[2,5]二烯-1,7'-环五[d]嘧啶]-4- 1核。这个序列，基于市售试剂从酸催化苯酚与5-溴嘧啶的亲电烷基化开始。随后，氧化，钯催化的Sonogashira交叉偶联反应和亲电旋环化，使目标产品具有良好的收率和简单的合成方案。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.