One-pot Synthesis of Substituted Pyridines from Alkyl Ketones and Enamines by the Nickel-catalyzed Dehydrogenation of Alkyl Ketones

The one-pot synthesis of substituted pyridines from alkyl ketones, Stork enamines, and ammonia is reported. This reaction involves the nickel-catalyzed dehydrogenation of the alkyl ketone and conjugate addition of the enamine, followed by condensation with an ammonium salt to yield the corresponding...

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Bibliographic Details
Published inChemistry letters Vol. 52; no. 3; pp. 148 - 151
Main Authors Ueno, Satoshi, Maeda, Ryohei, Kogure, Yuya, Kuwano, Ryoichi
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 05.03.2023
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Nickel catalyst
Pyridines
One-pot synthesis
BETA-FUNCTIONALIZATION
ARYLATION
2+2+2 CYCLOADDITION
C-H FUNCTIONALIZATION
SATURATED KETONES
INDOLES
AMINATION
LIGANDS
ESTERS
METAL
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Summary:The one-pot synthesis of substituted pyridines from alkyl ketones, Stork enamines, and ammonia is reported. This reaction involves the nickel-catalyzed dehydrogenation of the alkyl ketone and conjugate addition of the enamine, followed by condensation with an ammonium salt to yield the corresponding pyridine. Furthermore, the a-alkylation of 8-amino-y,8-unsatu-rated ketone intermediates leads to the synthesis of tetrasub-stituted pyridine in excellent yields by means of a three-step one-pot reaction.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.220546