Synthesis of highly substituted 2-pyridones (microreview)

Vodolazhenko, Maria A.; Gorobets, Nikolay Yu.

doi:10.1007/s10593-017-1982-3

Cited by 5 publications

(2 citation statements)

References 21 publications

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“…The use of piperidine as catalyst in i-PrOH under microwave irradiation at 100 ºC during 5 min [8] resulted in formation of pure expected product 8a, but the isolated yield was again very low (12%, Entry 9). Further experiments with catalytic amounts of piperidine, its stoichiometric quantities and excess at higher temperatures (Entries [10][11][12][13][14] showed that under such conditions increasing amounts of the undesired by-product 10a appeared in the isolated material. The reaction carried out at 160 °С during 20 min under microwave irradiation gave the pure by-product (10a, Entry 15).…”

Section: Search For Optimal Reaction Conditionsmentioning

confidence: 99%

“…All these factors can be used for the selectivity control in such reactions. In most of the above cited publications cyanoacetic acid amides and related acyclic derivatives of this acid were used as the active methylene nitriles [14]. However, heteroaryl substituted acetonitriles also have significant potential for the construction of complex heterocyclic systems in this approach [15].…”

Section: Introductionmentioning

confidence: 99%

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TWO-STAGE ONE-POT INTERACTION OF ACYCLIC Β-Ketoesters, DMFDMA AND 2-Cyanomethylbenzimidazole

Vodolazhenko¹,

Mykhailenko²,

Gorobets³

et al. 2017

Chemical Series

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A one-pot two-stage interaction of acyclic β-ketoesters, dimethylformamide dimethylacetal (DMFDMA) and 2-cyanomethylbenzimidazole was studied. Carried out under microwave irradiation in 2-propanol in the presence of piperidine, this transformation leads to the formation of 4-cyanobenzo [4,5]imidazo [1,2-α]pyridine-2-carboxylates, whereas at room temperature in methanol in the presence of sodium methylate 1-hydroxybenzo [4,5]imidazo[1,2-α]pyridine-4-carbonitriles are formed. Intermediate enamines initially formed from β-ketoesters and DMFDMA attack methylene group of 2-cyanomethylbenzimidazole followed by heterocyclizaton. In the presence of piperidine the benzimidazole nitrogen atom attacks the keto group of the β-ketoester fragment, whereas in the strong basic conditions cyclization occurs by the ester group.

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Section: Search For Optimal Reaction Conditionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

TWO-STAGE ONE-POT INTERACTION OF ACYCLIC Β-Ketoesters, DMFDMA AND 2-Cyanomethylbenzimidazole

Vodolazhenko¹,

Mykhailenko²,

Gorobets³

et al. 2017

Chemical Series

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Transition Metal‐Catalysed Direct C−H Bond Functionalizations of 2‐Pyridone Beyond C3‐Selectivity

Biswas

Maity

Pan

et al. 2020

Chemistry An Asian Journal

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Abstract2‐Pyridone is a ubiquitous motif in natural products, drug molecules, ligands in catalysis and organic materials. There is a necessity of direct step‐economic methods for the construction of 2‐pyridone based molecules. Strategically, the primary developments have led to the C3‐functionalizations due to the inherent reactivity of this center. Despite this, many elegant transition metal‐catalysed methods have been established to introduce versatile functional groups at the C4, C5 and C6‐position via direct C−H bond functionalizations. This minireview focuses on the categorized introduction of different functional groups at the 2‐pyridone scaffolds beyond C3‐selectivity and discusses substrate scope, limitations and plausible mechanistic details.

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A reaction of 2-carbonyl-substituted 1H-benzo[f]chromenes with N-arylamides of cyanoacetic acid

Osipov,

Krasnikov,

Artemenko

2024

Chem Heterocycl Comp

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Synthesis of highly substituted 2-pyridones (microreview)

Cited by 5 publications

References 21 publications

TWO-STAGE ONE-POT INTERACTION OF ACYCLIC Β-Ketoesters, DMFDMA AND 2-Cyanomethylbenzimidazole

TWO-STAGE ONE-POT INTERACTION OF ACYCLIC Β-Ketoesters, DMFDMA AND 2-Cyanomethylbenzimidazole

Transition Metal‐Catalysed Direct C−H Bond Functionalizations of 2‐Pyridone Beyond C3‐Selectivity

A reaction of 2-carbonyl-substituted 1H-benzo[f]chromenes with N-arylamides of cyanoacetic acid

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