Synthesis of N‐Substituted Condensed Tetrahydropyridine‐Based Enaminones via Palladium‐Catalyzed Intramolecular C–N Cross‐coupling

A number of β‐enaminones with secondary amino group (alkyl, cyclopropyl, and aryl) were prepared from corresponding β‐diketones. Two general protocols for their palladium‐catalyzed intramolecular C–N cross‐coupling were established to give corresponding N‐substituted condensed tetrahydropyridines in...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 55; no. 3; pp. 670 - 684
Main Authors Dousova, Hana, Ruzickova, Zdenka, Simunek, Petr
Format Journal Article
LanguageEnglish
Published HOBOKEN Wiley 01.03.2018
Wiley Subscription Services, Inc
Subjects
Aromatic compounds
Chemical synthesis
Chemistry
Chemistry, Organic
Coupling
Diketones
Organic compounds
Palladium
Physical Sciences
Science & Technology
Substitutes
Substrates
HALIDES
AMINATION
PRECATALYSTS
QUINOLINE
HETEROCYCLES
COMPLEXES
NITROGENATION-TRANSMETALATION PROCESS
NHC
DERIVATIVES
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Summary:A number of β‐enaminones with secondary amino group (alkyl, cyclopropyl, and aryl) were prepared from corresponding β‐diketones. Two general protocols for their palladium‐catalyzed intramolecular C–N cross‐coupling were established to give corresponding N‐substituted condensed tetrahydropyridines in good yields. The methodology is applicable for a wide variety of structural motifs. The work also extends the applicability of novel, recently established, palladium precatalysts to new substrates.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.3085