A FACILE METHOD FOR THE SYNTHESIS OF NOVEL PYRIDINONE DERIVATIVES VIA KETENE<i>N</i>,<i>S</i>-ACETALS

Al-Afaleq, Eljazi I.

doi:10.1081/scc-100106218

Cited by 13 publications

(8 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The N-cyclic maleamic acid is constructed such that due to the ring-cleaved structure of maleic anhydride (-COCH=C-HCOOH) that bonded to the amino group (NH2) of the starting N-cyclic amine via a malemic bond (-NH-CO-). (19) was allowed to react with malononitrile in the presence of few drops of piperidine as a catalyst it yielded 2-amino-6-[4-carboxy-6-(4-chloro-3-methylphenyl)-3-cya no-4H-pyran-2-ylamino]-3-cyano-4H-pyran-4-ca rboxylic acid (20). Compound (20) was obtained from Michael addition reaction (α,β-unsaturated amide rather than α,β-unsaturated acid) and gave an adduct through the fleeting intermediate which underwent ring closure to give the desired product.…”

Section: Resultsmentioning

confidence: 99%

“…(19) was allowed to react with malononitrile in the presence of few drops of piperidine as a catalyst it yielded 2-amino-6-[4-carboxy-6-(4-chloro-3-methylphenyl)-3-cya no-4H-pyran-2-ylamino]-3-cyano-4H-pyran-4-ca rboxylic acid (20). Compound (20) was obtained from Michael addition reaction (α,β-unsaturated amide rather than α,β-unsaturated acid) and gave an adduct through the fleeting intermediate which underwent ring closure to give the desired product. IR spectrum of (20) Refluxing maleamic acid derivative (19) with diethylmalonate in the presence of ammonium acetate in a water bath afforded 6-(4-chloro-3-methylphenyl)-3-cyano-2-[3,4,6-trioxo-3,3a,4,5, 6,7-hexahydro-2H-pyrrolo[3,4-c]pyridin-1ylamino)-4H-pyran-4-carboxylic acid (25).…”

Section: Resultsmentioning

confidence: 99%

“…The reaction mixture was allowed to cool at room temperature then acidified with diluted acetic acid (200 mL), the solid formed was filtered off, washed with water, dried and crystallized from the ethanol/water to afford bis compound (20).…”

Section: -Amino-6-[4-carboxy-6-(4-chloro-3-methylph Enyl)-3-cyano-4hmentioning

confidence: 99%

“…4H-Pyran derivative (4) (1.00 g, 3.4 mmol) in triethylorthoformate 18,19,20 (10 mL) was stirred under reflux for (5h). The reaction mixture was concentrated and the obtained brown precipitate then crystallized from ethanol/water to afford ethoxymethyleneamino-4H-pyran (6).…”

Section: -(4-chloro-3-methylphenyl)-3-cyano-2-(ethoxymethyleneamino)mentioning

confidence: 99%

See 3 more Smart Citations

Pyran and Pyridine as Building Blocks in Heterocyclic Synthesis

El‐Hashash¹,

El‐Sawy²,

Eissa³

2009

Journal of the Korean Chemical Society

View full text Add to dashboard Cite

ABSTRACT. The present work is devoted to study the interaction of β-aroylacrylic acid derivative (3) with malononitrile in (DMF) in the presence of piperidine and/or ammonium acetate, then using the formed compounds as starting materials for synthesizing fused and isolated heterocyclic systems. It has been established that the β-aroylacrylic acid (3) reacts with malononitrile in (DMF) in the presence of piperidine as a catalyst with the formation of 4H-pyran derivative (4). By changing the catalyst into ammonium acetate, pyridine derivative (5) has been obtained. Also the N-maleamic acid derivatives (19) and (27) have been synthesized via the interaction of (4) and (5) with maleic anhydride. The purpose of this step is to study the behavior of the formed maleamic acid derivatives -as analogies of β-aroylacrylic acids -towards different active methylene compounds under Michael addition reaction.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: -Amino-6-[4-carboxy-6-(4-chloro-3-methylph Enyl)-3-cyano-4hmentioning

confidence: 99%

Section: -(4-chloro-3-methylphenyl)-3-cyano-2-(ethoxymethyleneamino)mentioning

confidence: 99%

See 2 more Smart Citations

Pyran and Pyridine as Building Blocks in Heterocyclic Synthesis

El‐Hashash¹,

El‐Sawy²,

Eissa³

2009

Journal of the Korean Chemical Society

View full text Add to dashboard Cite

show abstract

“…Refluxing of 4 with neat triethyl-orthoformate (TEOF) [29][30][31] afforded 6-(4-bromophenyl)-3-cyano-2-(ethoxymethyleneamino) pyridine-4-carboxylic acid 11.Its IR displayed an absorption bands at 1645,1725,2220 and 3410 cm -1 attributable to C=N, C=O, CN. OH. and showed no absorption frequency in the NH region.…”

Section: Methodsmentioning

confidence: 99%

3-(4-Bromobenzoyl)prop-2-enoic acid as Precursor in Synthesis of Some Important Heterocyclic Compounds

El‐Hashash¹,

Rizk²,

Ahmed³

2012

CHEMISTRY

View full text Add to dashboard Cite

The present work deals with the generation and synthesis of different heterocycles such as 2-pyrimidine thione, pyrane, pyridine and phthalazinone derivative via the treatment of 3-(4-bromobenzoyl)prop-2-enoic acid with thiourea, ethylcyanoacetate malononitrile& acetylacetone in presence of amm.acetate and/or piperidine respectively.Additionally, utility of 2-amino-3-cyano-4-carboxy-6-(4-bromophenyl)3,4-dihydropyridine (4) as a key starting material to synthesize some important heterocycles include fused pyrido-pyrimidine,fused pyrido-pyridazinopyrimidine and interesting diheterocyclic amines.

show abstract

Sulfonamides incorporating ketene N,S‐acetal bioisosteres as potent carbonic anhydrase and acetylcholinesterase inhibitors

Istrefi

Türkeş

Arslan

et al. 2020

Archiv der Pharmazie

View full text Add to dashboard Cite

In this study, 15 novel compounds in a series of sulfonamide-based ketenes (7a-o) were synthesized and characterized using Fourier-transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectrometry. All compounds were tested for their ability to inhibit the human carbonic anhydrase (hCA) isoforms I and II, and acetylcholinesterase (AChE). The halogen-appended compounds, 7g, 7o, and 7i, exhibited the highest hCA I/II and AChE inhibition, with the K I values in the low nanomolar range (K I = 9.01 ± 0.08, 7.41 ± 0.03, and 7.37 ± 0.31 nM, respectively), as compared with their corresponding parent 2-[2,2-dicyano-1-(phenylamino) vinylthio]-N-(4-sulfamoylphenyl)acetamide analogs 7a-o. Besides, derivatives 7c and 7e selectively inhibited the isoform hCA I, whereas compounds 7m and 7n selectively inhibited isoform hCA II. These findings indicated that all compounds can inhibit metabolic dysfunctions, such as edema, epilepsy, glaucoma, and Alzheimer's disease, by specifically targeting both the hCA isoforms and AChE expression.Herein, also the interactions between ligands and receptors were highlighted through in silico molecular docking studies. The molecular mechanics-generalized Born surface area method was utilized to compute the binding free energy and the energy contribution of the critical residues in the active site was estimated. All these results would help us to perfectly understand the relationship between activity and structural characteristics of derivatives and to further improve newly and highly effective analogs targeting hCA and AChE.

show abstract

A FACILE METHOD FOR THE SYNTHESIS OF NOVEL PYRIDINONE DERIVATIVES VIA KETENEN,S-ACETALS

Cited by 13 publications

References 17 publications

Pyran and Pyridine as Building Blocks in Heterocyclic Synthesis

Pyran and Pyridine as Building Blocks in Heterocyclic Synthesis

3-(4-Bromobenzoyl)prop-2-enoic acid as Precursor in Synthesis of Some Important Heterocyclic Compounds

Sulfonamides incorporating ketene N,S‐acetal bioisosteres as potent carbonic anhydrase and acetylcholinesterase inhibitors

Contact Info

Product

Resources

About