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一种温和且通用的吡啶定向环加成方法的开发。

Development of a mild and versatile directed cycloaddition approach to pyridines.

作者信息

Bachollet Sylvestre P J T, Vivat Jérôme F, Cocker Dean C, Adams Harry, Harrity Joseph P A

机构信息

Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, S3 7HF (UK).

出版信息

Chemistry. 2014 Sep 26;20(40):12889-93. doi: 10.1002/chem.201403916. Epub 2014 Aug 21.

DOI:10.1002/chem.201403916
PMID:25145488
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4313684/
Abstract

The aza-Diels-Alder cycloaddition of 1,2,4-triazines with alkynes offers a rapid and convenient method for the synthesis of highly substituted pyridines, but often requires harsh conditions and long reaction times. The present study offers a solution to these limitations by use of a temporary tether established by a Lewis acid-base complexation of in situ generated alkynylboranes and triazines bearing a Lewis basic donor. The cycloaddition reactions take place within 20 min at 40 °C and provide direct access to a broad range of pyridines with complete and predictable regiocontrol. The carbonboron bond can be further functionalised by cross-coupling allowing further functionality to be introduced after cycloaddition.

摘要

1,2,4-三嗪与炔烃的氮杂狄尔斯-阿尔德环加成反应为合成高度取代的吡啶提供了一种快速便捷的方法，但通常需要苛刻的条件和较长的反应时间。本研究通过利用原位生成的炔基硼烷与带有路易斯碱供体的三嗪形成的路易斯酸碱络合作用所建立的临时连接基团，解决了这些限制。环加成反应在40℃下20分钟内即可完成，并能以完全可预测的区域选择性直接合成多种吡啶。碳-硼键可通过交叉偶联进一步官能化，从而在环加成后引入更多官能团。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae2a/4313684/5342a17cbc5c/chem0020-12889-f8.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae2a/4313684/5342a17cbc5c/chem0020-12889-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae2a/4313684/390d9bb9ae84/chem0020-12889-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae2a/4313684/447939a6d297/chem0020-12889-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae2a/4313684/5f70632dd858/chem0020-12889-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae2a/4313684/d981d7bbbe04/chem0020-12889-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae2a/4313684/07281b03549d/chem0020-12889-f3.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae2a/4313684/f9ce9bf4dea4/chem0020-12889-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae2a/4313684/5342a17cbc5c/chem0020-12889-f8.jpg

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