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可见光胺化/斯迈尔斯重排串联反应:合成酞嗪衍生物的方法

Visible light amination/Smiles cascade: access to phthalazine derivatives.

作者信息

Brachet Etienne, Marzo Leyre, Selkti Mohamed, König Burkhard, Belmont Philippe

机构信息

Université Sorbonne Paris Cité (USPC) , Université Paris Descartes , Faculté de Pharmacie de Paris , UMR CNRS 8638 (COMETE) , 4 avenue de l'Observatoire , 75006 Paris , France . Email:

University of Regensburg Faculty of Chemistry and Pharmacy , Institute of Organic Chemistry , Universitätsstraße 31 , 93053 Regensburg , Germany.

出版信息

Chem Sci. 2016 Aug 1;7(8):5002-5006. doi: 10.1039/c6sc01095d. Epub 2016 May 6.

DOI:10.1039/c6sc01095d
PMID:30155150
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6018559/
Abstract

We report the synthesis of various phthalazines a new cascade reaction, initiated by visible light photocatalysis, involving a radical hydroamination reaction followed by a radical Smiles rearrangement. Phthalazine derivatives are obtained in high yields and from a broad scope readily accessible -alkynylsulfonohydrazone precursors. The mild photoredox conditions ensure an excellent functional group tolerance. Application of this strategy to a one-pot protocol starting from the corresponding carbonyl compounds, and subsequent functionalization allow the rapid synthesis of structurally diverse structures.

摘要

我们报道了各种酞嗪的合成,这是一种由可见光光催化引发的新型级联反应,涉及自由基氢胺化反应,随后是自由基斯迈尔斯重排反应。酞嗪衍生物以高收率从广泛易得的炔基磺酰腙前体中获得。温和的光氧化还原条件确保了优异的官能团耐受性。将该策略应用于从相应羰基化合物开始的一锅法方案以及后续官能化,能够快速合成结构多样的化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3f1a/6018559/febdf81c80b3/c6sc01095d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3f1a/6018559/46e7943495d4/c6sc01095d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3f1a/6018559/dd37268d1c9a/c6sc01095d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3f1a/6018559/22b346430ee7/c6sc01095d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3f1a/6018559/febdf81c80b3/c6sc01095d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3f1a/6018559/46e7943495d4/c6sc01095d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3f1a/6018559/dd37268d1c9a/c6sc01095d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3f1a/6018559/22b346430ee7/c6sc01095d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3f1a/6018559/febdf81c80b3/c6sc01095d-s3.jpg

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