Synthesis of Tetrahydronaphthyridines from Aldehydes and HARP Reagents via Radical Pictet–Spengler Reactions

The combination of aldehydes with newly designed HARP (halogen amine radical protocol) reagents gives access to α-substituted tetrahydronaphthyridines. By using different HARP reagents, various regioisomeric structures can be prepared in a single operation. These products, which are of high value in...

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Bibliographic Details
Published in:Organic letters 2016-04, Vol.18 (8), p.1713-1715
Main Authors: Jackl, Moritz K, Kreituss, Imants, Bode, Jeffrey W
Format: Article
Language:English
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Summary:The combination of aldehydes with newly designed HARP (halogen amine radical protocol) reagents gives access to α-substituted tetrahydronaphthyridines. By using different HARP reagents, various regioisomeric structures can be prepared in a single operation. These products, which are of high value in medicinal chemistry, are formed in a predictable manner via a formal Pictet–Spengler reaction of electron-poor pyridines that would not participate in the corresponding polar reactions.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00523