Synthesis Of 2-pyridones Research Articles

Ring-Closing Metathesis as a Key Step in the Synthesis of 2-Pyridones and Pyridine Triflates

The ring-closing metathesis transformation has been employed to construct a library of functionalized 2-pyridones and pyridine triflates. Using this mild approach, a range of substituent patterns can be built into the aromatic core, including groups which can be demanding to incorporate using alternative protocols.

ChemInform Abstract: A Metathesis‐Based Approach to the Synthesis of 2‐Pyridones and Pyridines.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Design and synthesis of 2-pyridones as novel inhibitors of the Bacillus anthracis enoyl-ACP reductase

Enoyl-ACP reductase (ENR), the product of the FabI gene, from Bacillus anthracis ( BaENR) is responsible for catalyzing the final step of bacterial fatty acid biosynthesis. A number of novel 2-pyridone derivatives were synthesized and shown to be potent inhibitors of BaENR.

A Metathesis-Based Approach to the Synthesis of 2-Pyridones and Pyridines

The ring-closing metathesis reaction has been successfully employed to form a range of dihydropyridone intermediates, which are in the correct oxidation state to undergo a base-induced elimination to reveal the aromatic 2-pyridone. This mild and novel approach to six-membered heteroaromatic compounds then provides access to a wide variety of substituted pyridines in excellent overall yield.

Hilbert-Johnson Reaction under High Pressure: A Facile Preparation of 2-Pyridones

For the first time, a facile synthesis of 2-pyridones utilizing a classical Hilbert-Johnson reaction of 2-methoxypyridines with haloalkanes under high pressure has been achieved. The reactions were sensitive to steric hindrance of haloalkanes.

Selective synthesis of 2-pyridones and pyrimidine-2,4-diones by neutral rhodium(I) complex-catalyzed cyclocotrimerization of alkynes and isocyanates

A neutral rhodium(I) complex, ‘RhCl(PPh 3) 2’ generated by the combination of [RhCl(C 2H 4) 2] 2 with a fourfold amount of PPh 3, effectively catalyzed the cyclocotrimerization of alkynes ( 1) and isocyanates ( 2) to give 2-pyridones ( 3) and/or pyrimidine-2,4-diones ( 4), selectively, by controlling the molar ratio of alkynes ( 1) and isocyanates ( 2).

活性メチン化合物のアルキニルイミンおよびケトンへの共役付加反応を用いる新規合成反応

The development of the synthetic methods of functionalized 2-pyridones is important as a result of the large number of biologically active compounds containing a 2-pyridone structure and as dienes in Diels-Alder cycloadditions. Many methods for the synthesis of 2-pyridones have been reported. We have found a 5-alkoxycarbonyl-2-pyridone synthesis via the nucleophilic addition of malonic esters to alkynyl imines in good yields. It is also found that the reaction of β-keto esters with alkynyl imines give 5-acetyl-2-pyridones in good yields. On the other hand, the reactions of dialkynyl imines instead of alkynyl imines with active methine compounds give 3, 4, 5, 6-tetrasubstituted-2-pyridones. We have found that the reactions of alkynylpyridines, pyrimidine, or thiazoles with malonic esters give bicyclo-2-pyridones in moderate to good yields. The conjugate addition reactions of various cyclic β-keto esters with alkynyl imines proceed and then the intramolecular cyclization reactions take place. The subsequent cleavage reactions give two-atom enlarged carbocyclic products in good yields. We have also found the reactions of malonic esters or β-keto esters with alkynyl ketones give 5-alkoxycarbonyl-2-pyrones or 5-acetyl-2-pyrones in good yields.

Synthesis of 2-pyridones as tissue factor VIIa inhibitors

2-Pyridones were prepared from 2,6-dibromopyridine via a multi-step synthesis. A variety of chemical transformations, including regioselective nucleophilic addition and selective nitrogen alkylation, afforded the penultimate intermediate 9. A combination of two-dimensional NMR techniques to unequivocally assign the structure of 9 is described. Compound 9 was then used in a Suzuki coupling and further derivatized to afford the targeted tissue Factor VIIa inhibitors. These compounds were tested in several serine protease enzyme assays with biological activity reported.

Synthesis of (±)-desamino huperzine A

The first synthesis of desamino huperzine A 2 is described. Key steps are a double Michael addition into benzoquinone monoketal 4, a regiocontrolled double bond isomerisation and a novel pyridone synthesis involving a Michael addition of a β-keto ester into acrylonitrile.

Pyrazole, Pyridine and Pyridone Synthesis on Solid Support

Pyrazole, Pyridine and Pyridone Synthesis on Solid Support

Solid-phase synthesis of pyridones and pyridopyrazines as peptidomimetic scaffolds.

[formula: see text] We report the syntheses of peptidomimetic opioids containing the core structure N-alkyl-2-alkyl-2,3-dihydro-4-pyridone. By employing imines bound on a solid support and the Danishefsky diene, this [4 + 2] cyclocondensation reaction facilitates the synthesis of novel complex heterocycles. The central reaction is carried out under mild conditions and employs readily available building blocks. In this study we demonstrate the suitability of N-alkyl-2-alkyl-2,3-dihydro-4-pyridones as a central scaffold for peptidomimetics and establish the scope of this [4 + 2] cyclocondensation reaction with imino acids on a solid phase. We also combine the synthesis of diketopiperazines with the [4 + 2] cyclocondensation reaction to form a 9,9a-dihydro-2H-pyrido-[1,2a]- pyrazine-3,8(1,4-dialkyl)dione, a bicyclic molecule containing a pyridopyrazine core structure.

ChemInform Abstract: A Highly Efficient Multicomponent Synthesis of Pyridones and Pyrimidones by a [2 + 2 + 2] Strategy.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2+2+2] strategy

The reaction of N-silylated iminoethers with 2-substituted acetyl chlorides yields activated 2-azadienes. These were shown to react with electron-deficient acetylenic dienophiles to yield pyridones. They also react with quinones to give the corresponding aromatized cycloadducts in good yields. The reaction of 2-azadienes with activated nitriles provided a very practical route towards polysubstituted pyrimidones. A multicomponent protocol is reported which combines a N-t-butyldimethylsilyl iminoether, an acetyl chloride derivative and a dienophile in the presence of triethylamine without isolation of any intermediate. This provides an extremely practical and versatile route to various mono- and polycyclic azaaromatics with a predictable substitution pattern. Yields ranged from 43 % to 94 % for the complete sequence.

ChemInform Abstract: Reaction of Diaminodiene Diketones with Nucleophiles. Synthesis of 2‐Pyridone and 2‐Pyridinethione Derivatives.

ChemInformVolume 18, Issue 43 Heterocyclic Compounds ChemInform Abstract: Reaction of Diaminodiene Diketones with Nucleophiles. Synthesis of 2-Pyridone and 2-Pyridinethione Derivatives. A. K. SHANAZAROV, A. K. SHANAZAROV VNI khim.-farm. inst. im. Ordzhonikidze, Moskva 119021Search for more papers by this authorV. G. GRANIK, V. G. GRANIK VNI khim.-farm. inst. im. Ordzhonikidze, Moskva 119021Search for more papers by this author A. K. SHANAZAROV, A. K. SHANAZAROV VNI khim.-farm. inst. im. Ordzhonikidze, Moskva 119021Search for more papers by this authorV. G. GRANIK, V. G. GRANIK VNI khim.-farm. inst. im. Ordzhonikidze, Moskva 119021Search for more papers by this author First published: October 27, 1987 https://doi.org/10.1002/chin.198743205Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume18, Issue43October 27, 1987 RelatedInformation

Reaction of diendiaminodiketones with nucleophilic reagents. Synthesis of 2-pyridone and 2-pyridinethione derivatives

Reaction of diendiaminodiketones with nucleophilic reagents. Synthesis of 2-pyridone and 2-pyridinethione derivatives

ChemInform Abstract: Reinvestigation of Thesing′s Synthesis of 2‐Pyridones Using 1‐(Methylthio‐thiocarbonylmethyl)pyridinium Iodide.

AbstractSeveral attempts are made to prepare 4,6‐diaryl‐ 2‐pyridothiones Starting from the title compound (I) using Thesing′s procedure for the synthesis of pyridones.

A Facile Synthesis of 2-Pyridones by Nucleophilic Reaction on Pyran-2-thiones

A Facile Synthesis of 2-Pyridones by Nucleophilic Reaction on Pyran-2-thiones

Activated Nitriles in Heterocyclic Chemistry. A Novel Synthesis of Pyridones, Pyrazolo[1,5‐a]pyrimidines and Pyrazolo[1,5‐b]oxazines

AbstractSeveral new pyridones, pyrazolo[1,5‐a]pyrimidines and pyrazolo[1,5‐b]oxazines were prepared from the cyanoacetohydrazide derivatives 1, 11 and the cinnamonitrile derivatives 2a–c.

Modellkomplex des nickels für die cc verknüpfung von alkinen mit isocyanaten

Azanickelacyclopenten derivatives, which can easily be prepared from alkynes, isocyanates and nickel(0) compounds, are shown to be intermediates in the nickel-catalysed synthesis of 2-pyridones.

ChemInform Abstract: Synthesis of 2‐Pyridones by the Co‐Trimerization of Acetylenes and Isocyanates.

AbstractBei der Umsetzung von Isocyanaten mit Acetylenverbindungen entstehen in Gegenwart von Kobaltkatalysatoren 2‐Pyridonverbindungen.