142784-72-3Relevant articles and documents
Practical Chemoselective Acylation: Organocatalytic Chemodivergent Esterification and Amidation of Amino Alcohols with N-Carbonylimidazoles
Nelson, Hope,Richard, William,Brown, Hailee,Medlin, Abigail,Light, Christina,Heller, Stephen T.
supporting information, p. 22818 - 22825 (2021/09/13)
Chemoselective transformations are a cornerstone of efficient organic synthesis; however, achieving this goal for even simple transformations, such as acylation reactions, is often a challenge. We report that N-carbonylimidazoles enable catalytic chemodivergent aniline or alcohol acylation in the presence of pyridinium ions or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), respectively. Both acylation reactions display high and broad chemoselectivity for the target group. Unprecedented levels of chemoselectivity were observed in the DBU-catalyzed esterification: A single esterification product was obtained from a molecule containing primary aniline, alcohol, phenol, secondary amide, and N?H indole groups. These acylation reactions are highly practical as they involve only readily available, inexpensive, and relatively safe reagents; can be performed on a multigram scale; and can be used on carboxylic acids directly by in situ formation of the acylimidazole electrophile.
An efficient, economical and eco-friendly acylation of alcohols and amines by alum doped nanopolyaniline under solvent free condition
Behera, Satyaranjan,Patra, Braja N.
, (2021/08/06)
We report acylation of alcohols and amines employing acetic acid as an acylating agent in solvent free condition by using alum doped nanopolyaniline (NDPANI) as a catalyst. This environmentally benign method does not use corrosive acid anhydrides and acid chlorides for acylation and does not produce waste product. Also, a non-toxic potash alum was used for doping of polyaniline rather than corrosive acids. The reaction conditions represent an advance over established method not only in omitting the need for expensive catalysts or solvents but also in shortening the reaction time significantly. The advantages of this catalyst are non-hazardous, cheap, reusable, easy to prepare and handling.
Lipase-mediated selective acetylation of primary alcohols in ethyl acetate
de Souza, Ernane C.,Romero-Ortega, Moises,Olivo, Horacio F.
supporting information, p. 287 - 290 (2017/12/29)
An environmental friendly process to selectively acetylate primary alcohols was demonstrated. The esterification process consists of treatment of a primary alcohol in the presence of immobilized C. antarctica lipase (Novozyme-435) in ethyl acetate at room temperature. Primary alcohols were acetylated in the presence of secondary alcohols and phenols.
Efficient approach for the chemoselective acetylation of alcohols catalyzed by a novel metal oxide nanocatalyst CuO-ZnO
Albadi, Jalal,Alihosseinzadeh, Amir,Mardani, Mehdi
, p. 308 - 313 (2015/09/28)
A new method has been developed for the chemoselective acetylation of alcohols with acetic anhydride in the presence of phenols using a novel, recyclable CuO-ZnO nanocatalyst. The catalyst was synthesized using the co-precipitation method and characterized by N2 adsorption-desorption, X-ray diffraction, scanning electron microscopy, transmission electron microscopy and energy dispersion scanning analyses. Furthermore, this catalyst could be recycled up to six times without significant loss in its activity.
A novel silver nanoparticle embedded mesoporous polyaniline (mPANI/Ag) nanocomposite as a recyclable catalyst in the acylation of amines and alcohols under solvent free conditions
Mandi, Usha,Roy, Anupam Singha,Banerjee, Biplab,Islam, Sk. Manirul
, p. 42670 - 42681 (2015/02/19)
A mesoporous polyaniline/silver (mPANI/Ag) nanocomposite has been prepared using mesoporous organic polymer polyaniline with silver nitrate via radical polymerization of aniline monomer in the presence of hydrochloric acid. The mPANI/Ag nanocomposite has been characterized by powder X-ray diffraction (XRD), transmission electron microscopy (TEM), energy-dispersive X-ray spectra (EDX), Fourier transform infrared spectroscopy (FT-IR), and ultraviolet-visible absorption spectra (UV-vis). The XRD patterns indicated that the crystalline phase of Ag is cubic. TEM images show that the Ag nanoparticles are well dispersed in the mesoporous polyaniline matrix. The mPANI/Ag acts as an efficient heterogeneous nanocatalyst in the acylation of substituted amines and alcohols using acetic acid. The catalyst is air-stable, inexpensive, easy to prepare and can be reused several times without a significant decrease in activity and selectivity. This journal is
Practical, environment-benign and atom economic KOAc-catalysed deprotection of aryl TIPS ethers under mild fluoride-free conditions
Wang, Bing,Sun, Hui-Xia,Chen, Bo,Sun, Zhi-Hua
supporting information; experimental part, p. 1112 - 1114 (2010/04/23)
A KOAc-catalysed, fluoride-free protocol not only effects chemoselective deprotection of phenolic TIPS ethers without affecting acetal, ketal, carbamate, O-acetyl and aliphatic silyl ethers, but also improves its atom economy by recycling the silanol byproduct.
Microwave-accelerated selective acylation of (hydroxyalkyl)phenols using acid chlorides
Miyazawa, Toshifumi,Yamamoto, Masato,Maeda, Yuki
experimental part, p. 1092 - 1099 (2009/09/06)
Highly selective acylation of the alcoholic hydroxy group can be achieved with (hydroxyalkyl)phenols carrying both alcoholic and phenolic hydroxyls by the use of the most common acylating agents, acid chlorides, under microwave irradiation. Copyright Tayl
Biphenylamidine derivatives
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Page column 26, (2010/11/29)
The present invention is a biphenylamidine derivative represented by the formula (1) or a pharmaceutically acceptable derivative thereof: and the biphenylamidine derivative or the pharmaceutically acceptable derivative thereof is a novel compound which can be used as a clinically applicable FXa inhibitor.
Metal-catalyzed acyl transfer reactions of enol esters: Role of Y5(OiPr)13O and (thd)2Y(OiPr) as transesterification catalysts
Lin, Mei-Huey,RajanBabu
, p. 997 - 1000 (2007/10/03)
(equation presented) Primary and secondary alcohols react with vinyl or isopropenyl acetate at room temperature in the presence of catalytic amounts (0.05-1 mol percent) of Y5(OiPr)13O to give the corresponding esters. In selected cases, the yttrium catalyst promotes the selective O-acylation of amino alcohols without the formation of the amide. Enol esters also react with α-amino acid esters in the absence of a catalyst, at room temperature, to give the corresponding amides.
