Developments in the Chemistry of 2-Pyridone

Hamama, Wafaa S.; Waly, Mostafa I.; EL-Hawary, Ibrahim I.; Zoorob, Hanafi H.

doi:10.1080/00397911.2013.862836

Cited by 29 publications

(11 citation statements)

References 42 publications

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“…2-Pyridones are obviousa nd relevantc andidates: [13][14][15] the enamide embedded in their ring system is certainly not ap rivi-leged subunit for classical cross coupling via oxidative insertion/reductive elimination, whereas an iron catalyzed 1,6-addition is feasible since acyclic a,b,g,d-unsaturateda mides have previously been shown to react with aryl-Grignardr eagents in the presenceo fc atalytic amounts of FeCl 2 with high selectivity. [16,17] Indeed, the N-benzylated substrate 1,o nt reatment with PhMgBr and Fe(acac) 3 (5 mol %), gave product 2a in which the heterocyclic ring is intact (Table 1);u nder optimized conditions (THF, À45 8C), the yield was almostq uantitative (entry 6).…”

Section: Resultsmentioning

confidence: 99%

Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling

Huang

Fürstner

2019

Chemistry An Asian Journal

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In the presence of simple iron salts, 2‐pyridone derivatives react with Grignard reagents under mild conditions to give the corresponding 1,6‐addition products; if the reaction medium is supplemented with an aprotic dipolar cosolvent after the actual addition step, the intermediates primarily formed succumb to ring opening, giving rise to non‐thermodynamic Z,E‐configured dienoic acid amide derivatives which are difficult to make otherwise. Control experiments as well as the isolation and crystallographic characterization of a (tricarbonyl)iron pyridone complex suggest that the active iron catalyst generated in situ exhibits high affinity to the polarized diene system embedded into the heterocyclic ring system of the substrates, which likely serves as the actual recognition element.

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Section: Resultsmentioning

confidence: 99%

Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling

Huang

Fürstner

2019

Chemistry An Asian Journal

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“…Once more, stirring of 3 with halo compounds such as methyl iodide and ethyl bromoacetate at room temperature furnished the respective triazine derivatives 10 (major) and/or 11 (minor) (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Acaricidal Activity of Some New 1,2,4‐Triazine Derivatives

Hamama

El‐Bana

Mostafa

et al. 2018

Journal of Heterocyclic Chem

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A new series of 1,2,4‐triazine derivatives were designed, synthesized, and identified on the basis of IR, 1H‐NMR, 13C‐NMR, and EI‐MS spectral data. The potent acaricidal activity of 1,2,4‐triazine derivatives against eggs and adult female of Tetranychus urticae (Koch) was assessed compared with pyridaben under laboratory conditions. Structure acaricidal activity relationships of the promising 1,2,4‐triazine derivatives were analyzed for eggs and adult female; the nature and position of the substituents were important in demonstration of the activities.

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“…3.13.6. Pyridone Derivatives 2-Pyridone, the tautomer of 2-hydroxypyridine, is one of the privileged heteroaromatic rings in natural products, bioactive molecules and pharmaceutical agents [133,134]. Furthermore, pyridone fused with a benzene or heterocyclic ring gives rise to diverse heterocyclic systems with innumerable pharmacological properties.…”

Section: Chromone and Chromene Derivativesmentioning

confidence: 99%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many of such molecules are biologically active or at least have been submitted to any biological screen. The selected papers covered in this review must meet two mandatory requirements: (1) the reported products should be obtained via a multicomponent reaction; (2) the reported products should be biologically actives or at least tested for any biological property. Given the diversity of synthetic approaches utilized in MCRs, the highly diverse nature of the biological activities evaluated for the synthesized compounds, and considering their huge structural variability, much of the reported data are organized into concise schemes and tables to facilitate comparison, and to underscore the key points of this review.Molecules 2020, 25, 505 2 of 71 acetylcholinesterase inhibitors, anti-HIV, antimicrobial, antioxidant, anti-mycobacterial and anticancer activities ( Figure 1). It is noteworthy that 64% and 16% of the supporting literature found for this review correspond to heterocyclic structures with anticancer and antimicrobial activities, respectively. Scheme 2. Three-component synthesis of 3,4-dihydropyrimidinones/thiones type 7 under microwave irradiation, for anti-inflammatory activity.Patil et al., reported a one-pot pseudo-five-component synthesis of highly functionalized tetrahydropyridines 9 using Cu(OTf) 2 as catalyst, Scheme 3. In vitro anti-inflammatory activity of the obtained compounds 9 was determined against matrix metalloproteinases (MMPs) as MMP-2 and MMP-9 by using gelatin zymography [29]. Scheme 3. Multicomponent Cu(OTf) 2 catalyzed synthesis of substituted tetrahydropyridines 9 for anti-inflammatory activity.A highly diastereoselective synthesis (exclusively the cis isomer is formed), of chromeno β-lactam hybrids 13/14 was also achieved by an efficient one-pot three-component reaction between either 5,5-dimethylcyclohexane-1,3-dione (10a) or 4-hydroxycoumarin (10b), diverse benzaldehydes 11 and malononitrile (12), in the presence of DABCO under reflux conditions (Scheme 4). Scheme 4. Three-component synthesis of β-lactam hybrids 13/14 for anti-inflammatory activity.The synthesized compounds (13 in 80-95% yield) and (14 in 82-95% yield) were screened for anti-inflammatory activity (as well as for anticancer activity, please see Section 3.13.13. Compound 13b (Ar = 4-ClC 6 H 4 , Ar 1 = 4-MeC 6 H 4 ) was the most active of all the chromeno β-lactam hybrids 13/14 tested, with a 19.8 anti-inflammatory ratio, although, it resulted less active than the reference drug dexamethasone corticosteroid used for the treatment of rheumatoid and skin inflammation [30].

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Developments in the Chemistry of 2-Pyridone

Cited by 29 publications

References 42 publications

Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling

Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling

Synthesis and Acaricidal Activity of Some New 1,2,4‐Triazine Derivatives

Synthesis of Biologically Active Molecules through Multicomponent Reactions

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