From dicarbonylallene to 1-aryl-3,6-dimethyl-4-aminoaryl-2-pyridones: a one-pot versatile and uncatalyzed synthesis

Boisse, Thomas; Rigo, Benoı̂t; Millet, Régis; Hénichart, Jean‐Pierre

doi:10.1016/j.tet.2007.07.079

Cited by 19 publications

(4 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound PYR was synthesized as described previously by Boisse et al [ 35 ]. The reaction was performed between an amine (4-chloroaniline for Cpd PYR) and an allenic precursor ( Figure 8 ).…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Two New Compounds Containing Pyridinone or Triazine Heterocycles Have Antifungal Properties against Candida albicans

et al. 2022

View full text Add to dashboard Cite

Candidiasis, caused by the opportunistic yeast Candida albicans, is the most common fungal infection today. Resistance of C. albicans to current antifungal drugs has emerged over the past decade leading to the need for novel antifungal agents. Our aim was to select new antifungal compounds by library-screening methods and to assess their antifungal effects against C. albicans. After screening 90 potential antifungal compounds from JUNIA, a chemical library, two compounds, 1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-3,6-dimethylpyridin-2(1H)-one (PYR) and (Z)-N-(2-(4,6-dimethoxy-1,3,5-triazin-2-yl)vinyl)-4-methoxyaniline (TRI), were identified as having potential antifungal activity. Treatment with PYR and TRI resulted in a significant reduction of C. albicans bioluminescence as well as the number of fungal colonies, indicating rapid fungicidal activity. These two compounds were also effective against clinically isolated fluconazole- or caspofungin-resistant C. albicans strains. PYR and TRI had an inhibitory effect on Candida biofilm formation and reduced the thickness of the mannan cell wall. In a Caenorhabditis elegans infection model, PYR and TRI decreased the mortality of nematodes infected with C. albicans and enhanced the expression of antimicrobial genes that promote C. albicans elimination. Overall, PYR and TRI showed antifungal properties against C. albicans by exerting fungicidal activities and enhancing the antimicrobial gene expression of Caenorhabditis elegans.

show abstract

Section: Methodsmentioning

confidence: 99%

“…Using this strategy, all compounds from the PYR series (1) were obtained ( Figure 8 ). All the procedures and chemical characterizations of PYR compounds are detailed in the publication described by Boisse et al [ 35 ].…”

Section: Methodsmentioning

confidence: 99%

Two New Compounds Containing Pyridinone or Triazine Heterocycles Have Antifungal Properties against Candida albicans

et al. 2022

View full text Add to dashboard Cite

show abstract

“…The synthesis of compound 3 started from previously reported aldehyde 4 . Wittig olefination with (1-methoxycarbonylethyl)triphenylphosphonium bromide and further methyl ester reduction gave alcohol 11 in good yield. Formation of the corresponding xanthate and 3,3-sigmatropic thermal rearrangement furnished compound 12 as an epimeric mixture.…”

mentioning

confidence: 99%

Stereoselective Allylstannane Addition for a Convergent Synthesis of a Complex Molecule

et al. 2015

View full text Add to dashboard Cite

A convergent methodology with 13 lineal steps for the synthesis of phormidolides B and C macrocyclic core is described. Stereoselective formation of the tetrahydrofuran (THF) core was achieved using a stereocontrolled allylation reaction. The key step of the synthesis is a (Z)-1,5-anti stereoselective allylstannane addition where a new stereocenter and a trisubstituted double bond are formed simultaneously. Finally, Shiina macrolactonization conditions improved the yield of the final cyclization.

show abstract

“…The bromoacylamino ketones 2a (R 3 = H) were treated with triphenylphosphine (PPh 3 ) in anhydrous 1-methyl-2-pyrrolidinone (NMP) to yield triphenylphosphonium salts 3 . Synthesis of triphenylphosphonium salts from bromo derivatives in solution was reported on several occasions − and we observed phosphonium salt formation as a side-product during the Mitsunobu reaction on solid phase . Exposure of resins 3 to a base (triethylamine, TEA) afforded polymer-supported 1,5-dihydro-pyrrol-2-ones 4 .…”

Section: Resultsmentioning

confidence: 70%

Multiplicity of Diverse Heterocycles from Polymer-Supported α-Acylamino Ketones

Pudelová¹,

Krchňák²

2009

J. Comb. Chem.

View full text Add to dashboard Cite

Polymer-supported α-acylamino ketones were transformed to seven types of structurally unrelated heterocyclic compounds. Syntheses involved variety of chemical routes and comprised diverse chemistries (C-C, C=C, C-N, C=N, C-O bond formations). Different sizes of heterocycles (4-, 5-, 6-, and 7-membered rings) were prepared, including dihydro-pyrrol-2-ones, pyrazin-2-ones, dihydro-triazepin-6-ones, morpholin-3-ones, imidazoles, β-lactams, and isoquinolin-1-ones. Further elaboration to fused ring systems was also documented.

show abstract

From dicarbonylallene to 1-aryl-3,6-dimethyl-4-aminoaryl-2-pyridones: a one-pot versatile and uncatalyzed synthesis

Cited by 19 publications

References 39 publications

Two New Compounds Containing Pyridinone or Triazine Heterocycles Have Antifungal Properties against Candida albicans

Two New Compounds Containing Pyridinone or Triazine Heterocycles Have Antifungal Properties against Candida albicans

Stereoselective Allylstannane Addition for a Convergent Synthesis of a Complex Molecule

Multiplicity of Diverse Heterocycles from Polymer-Supported α-Acylamino Ketones

Contact Info

Product

Resources

About