Strategic Synthesis of Asymmetrically Substituted C4N4 Fluorophores

Synthesis ◽  
2021 ◽  
Author(s):  
Wei Xu ◽  
Miki Kohei ◽  
Masakatsu Shibasaki ◽  
Naoya Kumagai

C4N4 fluorophores comprise a recently disclosed new class of emissive organic molecules with modular synthetic capabilities. Herein we report a new synthetic protocol for asymmetrically diarylated C4N4 fluorescent materials. Direct monoarylation of 1-naphthol was exploited to suppress undesired diarylation and provide a free phenolic hydroxyl group for prospective linking to a molecule of interest. Installation of the second aromatic to acquire the fluorescent property was achieved by Suzuki-Miyaura cross-coupling.

Holzforschung ◽  
1994 ◽  
Vol 48 (s1) ◽  
pp. 140-145 ◽  
Author(s):  
Hsin-Tai Chen ◽  
Masamitsu Funaoka ◽  
Yuan-Zong Lai

2021 ◽  
Author(s):  
Eric Miller ◽  
Maciej Walczak

Stereoselective reactions at the anomeric carbon constitute the cornerstone of preparative carbohydrate chemistry. Here, we report the synthesis of axial C1 trifluoroborates and stereoselective C-arylation and etherification reactions under photoredox conditions. These reactions are characterized by high anomeric selectivities for 2-deoxysugars and broad substrate scope (24 examples), including disaccharides and trifluoroborates with free hydroxyl groups. Computational studies show that high axial selectivities for these reactions originate from a combination of kinetic anomeric effect of the intermediate C1 radical and stereoelectronic stabilization of Ni(III) through the metallo-anomeric effect. Taken together, this new class of carbohydrate reagents adds the palette of anomeric nucleophile reagents suitable for efficient installation C-C and Cheteroatom bonds.


2019 ◽  
Vol 91 (5) ◽  
pp. 865-874 ◽  
Author(s):  
Armando Córdova ◽  
Samson Afewerki ◽  
Rana Alimohammadzadeh ◽  
Italo Sanhueza ◽  
Cheuk-Wai Tai ◽  
...  

Abstract A sustainable strategy for the neat production and surface functionalization of nanocellulose from wood pulp is disclosed. It is based on the combination of organocatalysis and click chemistry (“organoclick” chemistry) and starts with nanocellulose production by organic acid catalyzed hydrolysis and esterification of the pulp under neat conditions followed by homogenization. This nanocellulose fabrication route is scalable, reduces energy consumption and the organic acid can be efficiently recycled. Next, the surface is catalytically engineered by “organoclick” chemistry, which allows for selective and versatile attachment of different organic molecules (e.g. fluorescent probes, catalyst and pharmaceuticals). It also enables binding of metal ions and nanoparticles. This was exemplified by the fabrication of a heterogeneous nanocellulose-palladium nanoparticle catalyst, which is used for Suzuki cross-coupling transformations in water. The disclosed surface functionalization methodology is broad in scope and applicable to different nanocelluloses and cellulose based materials as well.


Synlett ◽  
2004 ◽  
Vol 2004 (14) ◽  
pp. 2597-2599 ◽  
Author(s):  
Yoshiji Takemoto ◽  
Hideto Miyabe ◽  
Yousuke Yamaoka

2009 ◽  
Vol 2009 (4) ◽  
pp. 229-230 ◽  
Author(s):  
Nobuhiro Sato ◽  
Hiroyuki Endo

A mild methylation of phenolic hydroxyl groups with iodomethane was enabled in the presence of sodium bis(trimethylsilyl)amide at room temperature. The reverse reaction, namely demethylation of methyl phenyl ethers, was easily achieved by microwave heating with neat iodotrimethylsilane.


2021 ◽  
Author(s):  
Eric Miller ◽  
Maciej Walczak

Stereoselective reactions at the anomeric carbon constitute the cornerstone of preparative carbohydrate chemistry. Here, we report the synthesis of axial C1 trifluoroborates and stereoselective C-arylation and etherification reactions under photoredox conditions. These reactions are characterized by high anomeric selectivities for 2-deoxysugars and broad substrate scope (24 examples), including disaccharides and trifluoroborates with free hydroxyl groups. Computational studies show that high axial selectivities for these reactions originate from a combination of kinetic anomeric effect of the intermediate C1 radical and stereoelectronic stabilization of Ni(III) through the metallo-anomeric effect. Taken together, this new class of carbohydrate reagents adds the palette of anomeric nucleophile reagents suitable for efficient installation C-C and Cheteroatom bonds.


Author(s):  
Pallavi Kamble ◽  
Sailesh Wadher

 Objective: The objective of the present study was to synthesize a series of 3-hydroxychromone derivatives and to evaluate its in vitro antioxidant and antimicrobial activities.Methods: 3-hydroxy chromones were synthesized using an algar flynn oyamada method which includes oxidative cyclization of 2-hydroxy chalcones in basic solution by hydrogen peroxide. 2-hydroxy chalcones were synthesized by Claisen-Schmidt condensation of substituted 2-hydroxy acetophenones with substituted aromatic aldehydes using polyethylene glycol-400 as a recyclable solvent. The synthesized compounds were evaluated for in vitro antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay. In addition, these compounds were also screened for in vitro antibacterial and antifungal activity by agar cup method and Poison plate method, respectively.Results: The structures of the synthesized compounds were characterized by infrared, 1H nuclear magnetic resonance and mass spectroscopy. The antioxidant activity data revealed that all the synthesized derivatives exhibited good activity due to the presence of phenolic hydroxyl group, 4-oxo group and 2,3-double bond. Further, the activity increased with the introduction of a more phenolic hydroxyl group and adjacent methoxy group in the structure. The antimicrobial activity data showed that the compounds possess better antibacterial and antifungal activity which is attributed to the presence of phenolic hydroxyl group and 4-oxo group in the structure.Conclusions: The use of inexpensive, eco-friendly and readily available reagents, easy work-up and high purity of products makes the procedure a convenient and robust method for the synthesis of title compounds. The presence of phenolic hydroxyl group, 4-oxo group, and 2,3-double bond in the structure is responsible for their good antioxidant and antimicrobial activities.


1969 ◽  
Vol 22 (5) ◽  
pp. 935 ◽  
Author(s):  
RK Norris ◽  
S Sternhell

The preparation and physical properties of 27 compounds in the title series are described. Tautomerism, syn-anti isomerism, N.M.R. parameters, and the mechanism of isomerization are discussed. In this series of derivatives, the tautomeric equilibrium in dioxan solutions lies heavily towards the oxime form unless intramolecular hydrogen bonding between the substituent at C2 (or C6) and the phenolic hydroxyl group of the nitroso form is possible. The substituents at C2 (and C6) influence the position of the syn-anti equilibrium in the quinone monoxime forms through electronic effects.


1975 ◽  
Vol 6 (25) ◽  
pp. no-no
Author(s):  
D. B. ULISS ◽  
H. C. DALZELL ◽  
G. R. HANDRICK ◽  
J. F. HOWES ◽  
R. K. RAZDAN

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