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通过在茚中插入氮原子来合成异喹啉。

Nitrogen atom insertion into indenes to access isoquinolines.

作者信息

Finkelstein Patrick, Reisenbauer Julia C, Botlik Bence B, Green Ori, Florin Andri, Morandi Bill

机构信息

Laboratorium für Organische Chemie, ETH Zürich Vladimir-Prelog-Weg 3, HCI 8093 Zürich Switzerland

出版信息

Chem Sci. 2023 Feb 23;14(11):2954-2959. doi: 10.1039/d2sc06952k. eCollection 2023 Mar 15.

DOI:10.1039/d2sc06952k
PMID:36937579
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10016357/
Abstract

We report a convenient protocol for a nitrogen atom insertion into indenes to afford isoquinolines. The reaction uses a combination of commercially available phenyliodine(iii) diacetate (PIDA) and ammonium carbamate as the nitrogen source to furnish a wide range of isoquinolines. Various substitution patterns and commonly used functional groups are well tolerated. The operational simplicity renders this protocol broadly applicable and has been successfully extended towards the direct interconversion of cyclopentadienes into the corresponding pyridines. Furthermore, this strategy enables the facile synthesis of N labelled isoquinolines, using NHCl as a commercial N source.

摘要

我们报道了一种将氮原子插入茚以生成异喹啉的简便方法。该反应使用市售的二醋酸碘苯(III)(PIDA)和氨基甲酸铵作为氮源,可提供多种异喹啉。各种取代模式和常用官能团都能很好地耐受。操作简便使该方法具有广泛的适用性,并且已成功扩展到将环戊二烯直接转化为相应的吡啶。此外,该策略使用NHCl作为商业氮源,能够轻松合成N标记的异喹啉。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5072/10016357/668d9854500d/d2sc06952k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5072/10016357/cdccf4e099f4/d2sc06952k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5072/10016357/753da0ff7de9/d2sc06952k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5072/10016357/668d9854500d/d2sc06952k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5072/10016357/cdccf4e099f4/d2sc06952k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5072/10016357/753da0ff7de9/d2sc06952k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5072/10016357/668d9854500d/d2sc06952k-s3.jpg

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