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芳烃与5-溴嘧啶进行亲电烷基化反应以合成4-芳基-5-炔基嘧啶。

Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines.

作者信息

Shcherbakov Stanislav S, Magometov Artyom Yu, Shcherbakova Viktoriia Yu, Aksenov Alexander V, Domenyuk Dmitriy A, Zelensky Vladimir A, Rubin Michael

机构信息

Department of Chemistry, North Caucasus Federal University 1a Pushkin St. Stavropol 355009 Russian Federation

Department of General Practice Dentistry and Child Dentistry, Stavropol State Medical University 310 Mira Street Stavropol 355017 Russian Federation.

出版信息

RSC Adv. 2020 Mar 10;10(17):10315-10321. doi: 10.1039/d0ra01335h. eCollection 2020 Mar 6.

DOI:10.1039/d0ra01335h
PMID:35498620
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9050372/
Abstract

A new synthetic protocol for preparation of medicinally important 4-aryl-5-alkynylpyrimidines is described. The featured approach involves a sequence of chemo- and regioselective Brønsted acid-catalyzed electrophilic alkylation of arenes with 5-bromopyrimidine, followed by oxidative re-aromatization of the formed dihydropyrimidine ring. Finally, palladium-catalyzed Sonogashira cross-coupling reaction provided an end-game strategy.

摘要

描述了一种用于制备具有重要药用价值的4-芳基-5-炔基嘧啶的新合成方法。其特色方法包括一系列化学和区域选择性的布朗斯特酸催化的芳烃与5-溴嘧啶的亲电烷基化反应，随后对形成的二氢嘧啶环进行氧化再芳构化。最后，钯催化的Sonogashira交叉偶联反应提供了一种最终策略。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b18e/9050372/4bb22369df5b/d0ra01335h-s9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b18e/9050372/ece1ec541f3e/d0ra01335h-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b18e/9050372/ee3d8a86cc91/d0ra01335h-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b18e/9050372/a5ccd6d02a2c/d0ra01335h-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b18e/9050372/6703b9b44550/d0ra01335h-s8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b18e/9050372/4bb22369df5b/d0ra01335h-s9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b18e/9050372/ece1ec541f3e/d0ra01335h-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b18e/9050372/ede1b38c4f88/d0ra01335h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b18e/9050372/4b3f6f6e1edd/d0ra01335h-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b18e/9050372/ee3d8a86cc91/d0ra01335h-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b18e/9050372/a5ccd6d02a2c/d0ra01335h-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b18e/9050372/6703b9b44550/d0ra01335h-s8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b18e/9050372/4bb22369df5b/d0ra01335h-s9.jpg

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