A General Preparation of Pyridines and Pyridones via the Annulation of Ketones and Esters

Marcoux, Jean-François; Marcotte, Félix-Antoine; Wu, Jimmy; Dormer, Peter G.; Davies, Ian W.; Hughes, David L.; Reider, Paul J.

doi:10.1021/jo0155198

Cited by 52 publications

(21 citation statements)

References 28 publications

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“…1 21, 22 and 4 23, 24 were prepared according to the reported methods. The annulations of 4‐nitroacetophenone with the vinamidinium salts in the presence of hot ammonium acetate/acetic acid give the 2,5‐disubstituted pyridines in excellent yields 25–27. The nitro compounds were converted into the diamines 3 and 6 by the Pd‐catalyzed hydrazine reduction.…”

Section: Resultsmentioning

confidence: 99%

Syntheses and properties of polyimides derived from diamines containing 2,5‐disubstituted pyridine group

Xia

Guo

Qiu

et al. 2006

J of Applied Polymer Sci

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A series of novel homo-and copolyimides containing pyridine units were prepared from the heteroaromatic diamines, 2,5-bis (4-aminophenyl) pyridine and 2-(4-aminophenyl)-5-aminopyridine, with pyromelltic dianhydride (PMDA), and 3,3Ј, 4,4Ј-biphenyl tertracarboxylic dianhydride (BPDA) via a conventional two-step thermal imidizaton method. The poly(amic acid) precursors have inherent viscosities of 1.60 -9.64 dL/g (c ϭ 0.5 g/dL in DMAC, 30°C) and all of them can be cast and thermally converted into flexible and tough polyimide films. All of the polyimides show excellent thermal stability and mechanical properties. The polyimides have 10% weight loss temperature in the range of 548 -598°C in air. The glass transition temperatures of the PMDA-based samples are in the range of 395-438°C, while the BPDA-based polyimides show two glass transition temperatures (T g 1 and T g 2), ranging from 268 to 353°C and from 395 to 418°C, respectively. The flexible films possess tensile modulus in the range of 3.42-6.39 GPa, strength in the range of 112-363 MPa and an elongation at break in the range of 1.2-69%. The strong reflection peaks in the wide-angle X-ray diffraction patterns indicate that the polyimides have a high packing density and crystallinity. The polymer films are insoluble in common organic solvents exhibiting high chemical resistance.

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Section: Resultsmentioning

confidence: 99%

Syntheses and properties of polyimides derived from diamines containing 2,5‐disubstituted pyridine group

Xia

Guo

Qiu

et al. 2006

J of Applied Polymer Sci

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“…The effect of the base is shown to be critical (50)). Marcoux and col. have described the use of the 2-chloro-N,N-dimethylamino trimethinium hexafluorophosphate (CDT-phosphate) salt for the preparation of pyridines and pyridones via annulation of ketones and esters [186]. Marcoux and col. have described the use of the 2-chloro-N,N-dimethylamino trimethinium hexafluorophosphate (CDT-phosphate) salt for the preparation of pyridines and pyridones via annulation of ketones and esters [186].…”

Section: From C 3 + C 2 Building Blocksmentioning

confidence: 99%

New Synthetic Methods to 2-Pyridone Rings

Torres¹,

Gil²,

Parra

2005

COC

202

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The synthesis of a substituted 2-pyridone ring is a topical area of continuing interest due to the number of biologically active molecules containing this moiety. Over the last decade, natural compounds with this structure have emerged as potent antitumor antiviral and attention, because those compounds may be studied as a simple model for investigating mechanisms of some enzymatic reactions or for discerning the behavior of nucleic acids bases in connection with mutation due to base mispairing or other mistaken helices. Recent studies have shown the usefulness of 2-pyridones as intermolecular connectors between building blocks in material science. Thus, despite the large number of methods known for their synthesis, new procedures are continuously being developed. Two main synthetic approaches can be found in the literature: from other heterocycles systems or condensation of acyclic systems. The latter can be further classified depending on the bond formed in the cyclization step: by C-C or C-N bond generation. The latter can be subclassified depending on the first condensation step. This is a review of new or improved methods for constructing 2-pyridone rings. This article will be restricted to ring formation, which can be included in the total synthesis of several compounds with specific biological or material properties.The pursuit of these properties requires efficient synthetic routes that allow rapid assembly and variation of multiple pendant substituents on the heteroaromatic case, which permits rapid analogsynthesis (RAS) [1].

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“…We envisioned a milder way, relying on a [3+2+1] annulation strategy recently published by the Merck process group. 30,31 Here a vinamidinium salt 44 is reacted with the β-ketoester 43 and hydroxylamine in the presence of two bases to give directly pyridine-N-oxide 45. Mechanistic investigations confirmed that 46 and 47 are intermediates in this process.…”

Section: Pyridine-n-oxidesmentioning

confidence: 99%

Inhibitors of the hepatitis C virus RNA-dependent RNA polymerase

Attenni¹,

Avolio²,

Colarusso³

et al. 2006

Arkivoc

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Infections caused by Hepatitis C Virus (HCV) are a significant world health problem for which novel therapies are in urgent demand. The polymerase of HCV is responsible for the replication of viral RNA. We recently disclosed diketoacids 1 and dihydroxypyrimidine carboxylates 3 as novel, reversible inhibitors of the HCV NS5B polymerase. We report here the further development of 3 into the more potent 5,6-dihydroxy-2-(2-thienyl)pyrimidine-4-carboxylic acids. The structure activity relationship of these inhibitors is discussed in the context of their physicochemical properties, supporting the proposed binding model, which involves pyrophosphate like chelation of the active site Mg-ions. We also report on the discovery and synthesis of two related scaffolds, the N1-substituted pyrimidones and pyridine-N-oxides.

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A General Preparation of Pyridines and Pyridones via the Annulation of Ketones and Esters

Cited by 52 publications

References 28 publications

Syntheses and properties of polyimides derived from diamines containing 2,5‐disubstituted pyridine group

Syntheses and properties of polyimides derived from diamines containing 2,5‐disubstituted pyridine group

New Synthetic Methods to 2-Pyridone Rings

Inhibitors of the hepatitis C virus RNA-dependent RNA polymerase

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