Cleavage of Diethyl Chromonyl <font>α</font>-Aminophosponate with Nitrogen and Carbon Nucleophiles: A Synthetic Approach and Biological Evaluations of a Series of Novel Azoles, Azines, and Azepines Containing <font>α</font>-Aminophosphonate and Phosphonate Groups

Ali, Tarik E.; Abdel‐Aziz, Salah A.; El-Edfawy, Somaya M.; Mohamed, E. A.; Abdel‐Kariem, Somaia M.

doi:10.1080/00397911.2014.948965

Cited by 24 publications

(9 citation statements)

References 27 publications

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“…A single example of the reaction of 6-methyl-2-trifluoromethylchromene-4-thione with hydrazine hydrate in ethanol at room temperature provided the respective 3(5)-(2-hydroxy-5-methylphenyl)-5(3)-trifluoromethylpyrazole in 65% yield [ 81 ]. On the other hand, the reaction of diethyl [(4-chlorophenylamino)(6-methylchromon-3-yl)methyl]phosphonate with hydrazine hydrate and sodium ethoxide in refluxing ethanol led to the 3(5)-(2-hydroxy-5-methylphenyl)-4-(α-aminophosphonate)pyrazole in 97% yield [ 82 ]. This pyrazole showed a moderate antimicrobial activity and a good antioxidant effect [ 82 ].…”

Section: Chromones As Starting Materials In the Synthesis Of 3(5)-mentioning

confidence: 99%

“…On the other hand, the reaction of diethyl [(4-chlorophenylamino)(6-methylchromon-3-yl)methyl]phosphonate with hydrazine hydrate and sodium ethoxide in refluxing ethanol led to the 3(5)-(2-hydroxy-5-methylphenyl)-4-(α-aminophosphonate)pyrazole in 97% yield [ 82 ]. This pyrazole showed a moderate antimicrobial activity and a good antioxidant effect [ 82 ].…”

Section: Chromones As Starting Materials In the Synthesis Of 3(5)-mentioning

confidence: 99%

“…Only those chromones non-substituted at C-2 were allowed to react and a couple of 4-aryl-3(5)-(2-hydroxyaryl)-1-phenylpyrazoles were synthesized [ 80 ]. A single example of 1-phenyl-5-(2-hydroxy-5-methylphenyl)-3-(α-aminophosphonate)pyrazole 147 arose in 67% yield from the reaction of diethyl [(4-chlorophenylamino)(6-methylchromon-3-yl)methyl]phosphonate 146 with phenyl-hydrazine and sodium ethoxide in refluxing ethanol ( Scheme 49 ) [ 82 ]. Using the same procedure, 5-(2-hydroxyphenyl)-1-phenyl-4-[(1,3-thiazolidine-2,4-dione)methylene]-pyrazole arose from 5-[(chromon-3-yl)methylene]-1,3-thiazolidine-2,4-dione, in 63% yield [ 75 ].…”

Section: Chromones As Starting Materials In the Synthesis Of 3(5)-mentioning

confidence: 99%

“… Reaction of diethyl [(4-chlorophenylamino)(6-methylchromon-3-yl)methyl]phosphonate 146 with phenylhydrazine and sodium ethoxide in refluxing ethanol [ 82 ]. …”

Section: Figure and Schemesmentioning

confidence: 99%

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Synthesis of Chromone-Related Pyrazole Compounds

Santos

Silva

2017

Molecules

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Chromones, six-membered oxygen heterocycles, and pyrazoles, five-membered two-adjacent-nitrogen-containing heterocycles, represent two important classes of biologically active compounds. Certain derivatives of these scaffolds play an important role in medicinal chemistry and have been extensively used as versatile building blocks in organic synthesis. In this context, we will discuss the most relevant advances on the chemistry that involves both chromone and pyrazole rings. The methods reviewed include the synthesis of chromone-pyrazole dyads, synthesis of chromone-pyrazole-fused compounds, and chromones as starting materials in the synthesis of 3(5)-(2-hydroxyaryl)pyrazoles, among others. This review will cover the literature on the chromone and pyrazole dual chemistry and their outcomes in the 21st century.

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Section: Chromones As Starting Materials In the Synthesis Of 3(5)-mentioning

confidence: 99%

Section: Chromones As Starting Materials In the Synthesis Of 3(5)-mentioning

confidence: 99%

Section: Chromones As Starting Materials In the Synthesis Of 3(5)-mentioning

confidence: 99%

“… Reaction of diethyl [(4-chlorophenylamino)(6-methylchromon-3-yl)methyl]phosphonate 146 with phenylhydrazine and sodium ethoxide in refluxing ethanol [ 82 ]. …”

Section: Figure and Schemesmentioning

confidence: 99%

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Synthesis of Chromone-Related Pyrazole Compounds

Santos

Silva

2017

Molecules

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“…24,25 Only a few examples have been described in the literature for the Kabachnik-Fields reaction of 3-formylchromones, primary amines and dialkyl-(DAP) or trialkyl phosphites (TAP) (Table 1). [26][27][28][29][30][31][32] In four cases, the (4-oxo-4H-chromen-3-yl)phosphonates (3−6) were synthesized in the presence of a catalyst. [26][27][28][29] In the first two examples, the condensation was performed using rhodium-boron nitride or yttria-zirconia as a catalyst in acetonitrile for long reaction time (Table 1/Entries 1 and 2).…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of α-aminophosphonate-chromone hybrids using Kabachnik-Fields Reaction

Szabó¹,

Akaili²,

Tajti³

et al. 2022

Arkivoc

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An efficient, practical, and green approach for the synthesis of α-aminophosphonates incorporating a chromone moiety by the one-pot Kabachnik-Fields reaction has been developed. The three-component reactions of 3-formylchromones, primary amines and dialkyl phosphites was carried out in short reaction times in the absence of any catalyst or solvent under microwave irradiation. The method developed did not require column chromatographic separation since the products could be recovered from the reaction mixture by simple filtration. The method developed could be applied to a range of primary amines and dialkyl phosphites, which confirmed the large scope and functional-group tolerance.

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Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

2020

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Scheme 20. Phosphonation of pyridinones.Scheme 21. CuI-catalyzed phosphoramidate formation.Scheme22. Phosphonation of coumarin and quinolinone.Scheme23. Silver(I)-catalyzed phosphonation of coumarins. Scheme 33. Electrochemical C(sp 2 )ÀHphosphonation of quinoxaline-2(1H)-ones. Scheme 39. Phosphorylation of quinoxaline-2(1 H)-ones. Scheme40. Autoxidative phosphorylation of quinoxalines. Scheme 41. DTBP-mediated formation of phosphonated benzothiazoles. Scheme42. Phosphonation of imidazole[2,1-b]thiazoles.Scheme 47. Copper(I)-catalyzedp hosphonationo fN-iminoisoquinolinium ylides. Scheme48. Aerobic phosphonationofC ( sp 3 ) À Hbonds. Scheme 49. Copper(II)/PBQ-catalyzed phosphorylation of 3,4-dihydro-1,4-benzoxazin-2-ones. Scheme 87. Asymmetric exo-selective [3+ +2] cycloaddition to afford phosphorus-substituted pyrrolidines. Scheme 95. Cascade condensation/cyclization to phosphonylated thienopyridines. Scheme 96. S N Ar'-involved cascade reactions to phosphonylated oxygenorn itrogen heterocycles.Scheme 97. Manganese(III)-mediated synthesis of 3-phosphonyldihydrofuransfrom b-ketophosphonates.Scheme98. Cyclization to phosphonated isochromenes.Scheme 121. Asymmetric [4+ +2] cycloaddition of b,g-unsaturated a-ketophosphonates.

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Cleavage of Diethyl Chromonyl α-Aminophosponate with Nitrogen and Carbon Nucleophiles: A Synthetic Approach and Biological Evaluations of a Series of Novel Azoles, Azines, and Azepines Containing α-Aminophosphonate and Phosphonate Groups

Cited by 24 publications

References 27 publications

Synthesis of Chromone-Related Pyrazole Compounds

Synthesis of Chromone-Related Pyrazole Compounds

Microwave-assisted synthesis of α-aminophosphonate-chromone hybrids using Kabachnik-Fields Reaction

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

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