Paper
Design and Synthesis of Novel 2-Hydroxy-1,4-Benzoxazine Derivatives through Three-Component Petasis Reaction Catalysed by Pyridinium Toluene-Sulphonate
Published Aug 1, 2016 · S. Mahdjoub, Chamseddine Derabli, R. Boulcina
Journal of Chemical Research
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4
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0
Influential Citations
Abstract
A variety of novel 2-hydroxy-1,4-benzoxazines were synthesised through the Petasis multicomponent reaction of 2-[(arylmethyl)amino] phenols with arylboronic acids and glyoxal catalysed by pyridinium toluene-p-sulphonate. A plausible reaction mechanism has also been proposed.
Study Snapshot
The three-component Petasis reaction catalyzed by pyridinium toluene-p-sulphonate successfully synthesized novel 2-hydroxy-1,4-benzoxazine derivatives, offering a promising reaction mechanism.
PopulationOlder adults (50-71 years)
Sample size24
MethodsObservational
OutcomesBody Mass Index projections
ResultsSocial networks mitigate obesity in older groups.
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References
A New and Efficient One‐Pot Synthesis of 2‐Hydroxy‐1,4‐dihydrobenzoxazines via a Three‐Component Petasis Reaction.
A one-pot Petasis multicomponent reaction efficiently synthesizes new 2-hydroxy-2H-1,4-benzoxazine derivatives with good to excellent yields from secondary amines synthesized from 2-aminophenols and aromatic aldehydes.
2014·15citations·Louisa Chouguiat et al.·ChemInform
ChemInform
4-(2-Nitrobenzyl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazin-2-ol
The crystal structure of C21H18N2O4 shows a three-dimensional network of hydrogen bonds, forming sheets parallel to (010) and linking them together.
2014·2citations·Louisa Chouguiat et al.·Acta Crystallographica Section E: Structure Reports Online
Acta Crystallographica Section E: Structure Reports Online
Enantioselective organocatalytic three-component Petasis reaction among salicylaldehydes, amines, and organoboronic acids.
The new thiourea-binol catalyst enables the enantioselective three-component Petasis reaction, yielding a broad range of alkylaminophenols with high enantioselectivity (up to 95%).
2012·56citations·Wenyong Han et al.·Organic letters
Organic letters
An efficient cascade synthesis of various 2H-1,4-benzoxazin-3-(4H)-ones from o-halophenols and 2-halo-amides catalyzed by CuI.
Copper-catalyzed coupling of o-halophenols and 2-halo-amides efficiently synthesizes various 2H-1,4-benzoxazin-3-(4H)-ones with diverse substituents in good to excellent yields.
2009·43citations·Dingben Chen et al.·Organic & biomolecular chemistry
Organic & biomolecular chemistry
One-pot regioselective annulation toward 3,4-dihydro-3-oxo-2H-1,4-benzoxazine scaffolds under controlled microwave heating
This study demonstrates an efficient one-pot synthesis of 2-alkyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazines under controlled microwave heating, with good to excellent yields.
2006·30citations·Gaofeng Feng et al.·Tetrahedron
Tetrahedron
Citations
Efficient synthesis, crystal structure, Hirshfeld surface analysis, biological evaluation, DFT calculations and Docking study of pyrano[4,3-b]pyran derivatives
This study presents a simple and rapid method for synthesis of pyrano[4,3-b]pyran derivatives, with potential antimicrobial and Alzheimer's activities, and confirms their molecular structure through X-ray diffraction analysis.
2023·3citations·Yasmine Zine et al.·Journal of Molecular Structure
Journal of Molecular Structure
Reactivity and Synthetic Applications of Multicomponent Petasis Reactions
The Petasis reaction offers efficient access to highly functionalized amines with high diastereoselectivity and enantioselectivity, enabling the synthesis of complex natural-product-like heterocycles and biologically interesting molecules.
2019·149citations·Peng Wu et al.·Chemical Reviews
Chemical Reviews
New eco-friendly procedure for the synthesis of 4-arylmethylene-isoxazol-5(4H)-ones catalyzed by pyridinium p-toluenesulfonate (PPTS) in aqueous medium
This new, eco-friendly method for synthesis of 4-arylmethylene-isoxazol-5(4H)-ones using PPTS offers good yields, short reaction times, simplicity, and respect for the environment.
2018·30citations·Rima Laroum et al.·Synthetic Communications
Synthetic Communications
Sonochemistry – an innovative opportunity towards a one-pot three-component synthesis of novel pyridylpiperazine derivatives catalysed by meglumine in water
Sonochemistry enables rapid access to diverse functionalized pyridyl piperazine derivatives with low catalyst loading, shorter reaction time, and excellent green chemistry metrics.
2017·8citations·S. Tabassum et al.·New Journal of Chemistry
New Journal of Chemistry