scholarly journals Hydroxylamine-mediated C–C amination via an aza-hock rearrangement

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Tao Wang ◽  
Philipp M. Stein ◽  
Hongwei Shi ◽  
Chao Hu ◽  
Matthias Rudolph ◽  
...  
Keyword(s):  
Transition Metals ◽  
Benzyl Alcohol ◽  
Substituted Anilines ◽  
Reaction Conditions ◽  
Benzyl Alcohols ◽  
Simple Route ◽  
Reduction Sequence

AbstractDespite the widespread use of anilines, synthetic challenges to these targets still exist. Selectivity is often an issue, when using the traditional nitration-reduction sequence or more modern approaches, including arene C–H aminations catalyzed by transition metals, photosensitizers, or electrodes. Accordingly, there is still a need for general methods to rapidly, directly access specific isomers of substituted anilines. Here, we report a simple route towards the synthesis of such motifs starting from benzyl alcohols, which are converted to anilines by the use of arylsulfonyl hydroxylamines, via an aza-Hock rearrangement. Good to excellent yields are observed. The method is applicable to various benzyl alcohol surrogates (such as ethers, esters, and halides) as well as simple alkylarenes. Functionalizations of pharmaceutically relevant structures are feasible under the reaction conditions. Over ten amination reagents can be used, which facilitates the rapid assembly of a vast set of compounds.

Naturally Occurring Organic Acid-catalyzed Facile Diastereoselective Synthesis of Biologically Active (E)-3-(arylimino)indolin-2-one Derivatives in Water at Room Temperature

2019 ◽  
Vol 23 (16) ◽  
pp. 1778-1788 ◽  
Author(s):  
Gurpreet Kaur ◽  
Arvind Singh ◽  
Kiran Bala ◽  
Mamta Devi ◽  
Anjana Kumari ◽  
...  
Keyword(s):  
Room Temperature ◽  
Biologically Active ◽  
Environmentally Benign ◽  
Diastereoselective Synthesis ◽  
Substituted Anilines ◽  
Reaction Conditions ◽  
Naturally Occurring ◽  
Acid Catalyzed ◽  
Reaction Media ◽  
Column Chromatographic

A simple, straightforward and efficient method has been developed for the synthesis of (E)-3-(arylimino)indolin-2-one derivatives and (E)-2-((4-methoxyphenyl)imino)- acenaphthylen-1(2H)-one. The synthesis of these biologically-significant scaffolds was achieved from the reactions of various substituted anilines and isatins or acenaphthaquinone, respectively, using commercially available, environmentally benign and naturally occurring organic acids such as mandelic acid or itaconic acid as catalyst in aqueous medium at room temperature. Mild reaction conditions, energy efficiency, good to excellent yields, environmentally benign conditions, easy isolation of products, no need of column chromatographic separation and the reusability of reaction media are some of the significant features of the present protocol.

Synthesis and characterization of a novel oxo-bridged binuclear iron(iii) complex: its catalytic application in the synthesis of benzoxazoles using benzyl alcohol in water

2018 ◽  
Vol 42 (9) ◽  
pp. 7230-7236
Author(s):  
Elham Safaei ◽  
Zahra Alaji ◽  
Farhad Panahi ◽  
Andrzej Wojtczak ◽  
Janez Zvonko Jagličić
Keyword(s):  
Benzyl Alcohol ◽  
Synthesis And Characterization ◽  
Efficient Catalyst ◽  
Benzyl Alcohols ◽  
Catalytic Application ◽  
Binuclear Iron

A novel oxo-bridged binuclear iron(iii) complex was found to be an efficient catalyst in the synthesis of benzoxazoles from benzyl alcohols.

The regioselective coupling of 2-arylquinazolinone C–H with aldehydes and benzyl alcohols under oxidative conditions

2020 ◽  
Vol 44 (39) ◽  
pp. 16697-16701
Author(s):  
Umesh A. Kshirsagar ◽  
Deepali S. Waghmare ◽  
Shrikant D. Tambe
Keyword(s):  
Benzyl Alcohol ◽  
Oxidative Coupling ◽  
Benzyl Alcohols ◽  
Dehydrogenative Coupling ◽  
Palladium Catalyzed ◽  
Directing Group

Palladium catalyzed direct and regioselective cross dehydrogenative coupling (CDC) of 2-arylquinazoline-4-one endowed with a quinazolinone nucleus as an inherent directing group with aldehyde and oxidative coupling with benzyl alcohol was developed.

Synthesis, Generic Dyeing of Nindigo Derivatives on Unmodified Polypropylene; First Time Application in Dyeing Technology

2019 ◽  
Vol 19 (11) ◽  
pp. 7105-7111 ◽  
Author(s):  
Raju Penthala ◽  
Rangaraju Satish Kumar ◽  
Hyorim Kim ◽  
Gisu Heo ◽  
Young-A Son
Keyword(s):  
Mass Spectrometry ◽  
Polypropylene Fiber ◽  
Blue Color ◽  
Substituted Anilines ◽  
Simple Route ◽  
H Nmr ◽  
Dispersing Agent ◽  
Didodecyldimethylammonium Bromide ◽  
First Time ◽  
C Nmr

Hydrophobic nindigo dyes were designed and successfully synthesized from indigo by reacting with substituted anilines in a simple route. Four nindigo dyes were fruitfully analyzed by 1H NMR 13C NMR, electronic and mass spectrometry. Here, we have firstly introduced these nindigo dyes into dyeing area for the dyeing of unmodified polypropylene fiber in aqueous medium. Dyeing experiments has been performed by using didodecyldimethylammonium bromide dispersing agent to make dye-dispersant complex for enhancing the dispersion of dyes. All the dyes were displayed profound blue color hue on polypropylene. The dyeing efficiency and dye fixation order of the nindigo dyes are 3d > 3c ≥ 3b > 3a. Compound 3d having higher the hydrophobic character (logP ═ 7.04), so greater the dye ability on the polypropylene fiber and exhibiting deep coloration.

scholarly journals Aroylhydrazone Schiff Base Derived Cu(II) and V(V) Complexes: Efficient Catalysts towards Neat Microwave-Assisted Oxidation of Alcohols

2020 ◽  
Vol 21 (8) ◽  
pp. 2832
Author(s):  
Manas Sutradhar ◽  
Tannistha Roy Barman ◽  
Armando J. L. Pombeiro ◽  
Luísa M. D. R. S. Martins
Keyword(s):  
Schiff Base ◽  
Aliphatic Alcohol ◽  
Cinnamyl Alcohol ◽  
X Ray Diffraction ◽  
Reaction Conditions ◽  
Benzyl Alcohols ◽  
X Ray ◽  
Microwave Assisted ◽  
Tert Butyl Hydroperoxide ◽  
Oxidation Of Alcohols

A new hexa-nuclear Cu(II) complex [Cu3(μ2-1κNO2,2κNO2-L)(μ-Cl)2(Cl)(MeOH)(DMF)2]2 (1), where H4L = N′1,N′2-bis(2-hydroxybenzylidene)oxalohydrazide, was synthesized and fully characterized by IR spectroscopy, ESI-MS, elemental analysis, and single crystal X-ray diffraction. Complex 1 and the dinuclear oxidovanadium(V) one [{VO(OEt)(EtOH)}2(1κNO2,2κNO2-L)]·2H2O (2) were used as catalyst precursors for the neat oxidation of primary (cinnamyl alcohol) and secondary (1-phenyl ethanol, benzhydrol) benzyl alcohols and of the secondary aliphatic alcohol cyclohexanol, under microwave irradiation using tert-butyl hydroperoxide (TBHP) as oxidant. Oxidations proceed via radical mechanisms. The copper(II) compound 1 exhibited higher catalytic activity than the vanadium(V) complex 2 for all the tested alcohol substrates. The highest conversion was found for 1-phenylethanol, yielding 95.3% of acetophenone in the presence of 1 and in solvent and promoter-free conditions. This new Cu(II) complex was found to exhibit higher activity under milder reaction conditions than the reported aroylhydrazone Cu(II) analogues.

Kinetics and Mechanism of the Oxidation of Substituted Benzyl Alcohols by oxo(salen)manganese(V) complexes

2001 ◽  
Vol 2001 (5) ◽  
pp. 179-181 ◽  
Author(s):  
Vinita Kumbhat ◽  
Pradeep K. Sharma ◽  
Kalyan K. Banerji
Keyword(s):  
Hydrogen Atom ◽  
Benzyl Alcohol ◽  
Hydrogen Atom Transfer ◽  
Kinetics And Mechanism ◽  
Atom Transfer ◽  
Benzyl Alcohols ◽  
Hydride Ion ◽  
Oxidation Of Benzyl Alcohol

The oxidation of benzyl alcohol by oxo(salen)manganese (V) complexes proceeds via either a hydride-ion or a hydrogen-atom transfer from the alcohol to the manganese (V) complexes.

Preparation and Test of Hierarchical α-Ni(OH)2 Flowers and Spheres

2011 ◽  
Vol 311-313 ◽  
pp. 494-497
Author(s):  
Chang Yu Li ◽  
Li Li Liu ◽  
Shou Xin Liu
Keyword(s):  
Hierarchical Structures ◽  
Experimental Results ◽  
Reaction Conditions ◽  
Sem Images ◽  
Simple Route ◽  
Α Phase ◽  
Ft Ir

α-Ni(OH)2 with hierarchical structures were synthesized via a simple route using Ni(NO3)2•6H2O and urea as the starting materials. The experimental results from XRD and FT-IR showed that the samples prepared by this method had the typical α-phase and the size of samples can be control by adjusting the reaction conditions. SEM images showed many uniform flowerlike or spherelike architectures with diameters of 4-6μm consisted of dozens of nanosheets. The effects of nickel sources on the phase and morphology of the prepared samples were studied, the nickel sources had an effect on both the crystallinity and size of the prepared samples.

scholarly journals La(OH)3 nanoparticles immobilized on Fe3O4@chitosan composites as novel magnetic nanocatalysts for sonochemical oxidation of benzyl alcohol to benzaldehyde

RSC Advances ◽  
2021 ◽  
Vol 11 (57) ◽  
pp. 35988-35993
Author(s):  
Fereshteh Javidfar ◽  
Manoochehr Fadaeian ◽  
Javad Safaei Ghomi
Keyword(s):  
Benzyl Alcohol ◽  
Benzyl Alcohols ◽  
Oxidation Of Benzyl Alcohol ◽  
Sonochemical Oxidation

A sustainable synthesis of novel Fe3O4@CS/La(OH)3 as a nanocatalyst for oxidation of benzyl alcohols to benzaldehydes has been developed.

Metal-Free Halogenation of N-Substituted Enaminoesters and Enaminones: A Facile Access to Functionalized α,α-Dihaloimines

Synthesis ◽  
2020 ◽  
Vol 52 (08) ◽  
pp. 1301-1314 ◽  
Author(s):  
Changfu Qiu ◽  
Heshui Yu ◽  
Chuanjiang Qiu ◽  
Fangyi Li ◽  
Tongchuan Suo ◽  
...  
Keyword(s):  
Transition Metals ◽  
Building Blocks ◽  
Synthetic Method ◽  
Safe Operation ◽  
Reaction Conditions ◽  
Metal Free ◽  
Synthetic Utility ◽  
General Method

An efficient and general method for the synthesis of functionalized α,α-dihaloimines via halogenation of N-substituted enaminoesters and enaminones is described. This reaction, in which both α,α-dihaloimines and mixed α,α-dihaloimines could be achieved in good to excellent yields, is believed to proceed via an α-monohalogenated enamine intermediate. This synthetic method features no use of transition metals, readily accessible substrates, mild reaction conditions, simple and safe operation, and gram scale synthesis. Furthermore, the synthetic utility of the products was demonstrated by their efficient transformations to further useful nitrogen-containing heterocycles and building blocks.

scholarly journals Selective Liquid Phase Hydrogenation of Benzaldehyde to Benzyl Alcohol Over Alumina Supported Gold

2019 ◽  
Vol 150 (3) ◽  
pp. 881-887
Author(s):  
Yufen Hao ◽  
Chiara Pischetola ◽  
Fernando Cárdenas-Lizana ◽  
Mark A. Keane
Keyword(s):  
Liquid Phase ◽  
Benzyl Alcohol ◽  
Reaction Conditions ◽  
Liquid Phase Hydrogenation ◽  
Alcohol Water ◽  
Reaction Constant ◽  
Supported Gold ◽  
First Time ◽  
Nucleophilic Mechanism ◽  
By Products

Abstract We report for the first time 100% benzyl alcohol yield from the liquid phase (T = 353 K, P = 9 bar) hydrogenation of benzaldehyde over Au/Al2O3. Under the same reaction conditions, a benchmark Pt/Al2O3 catalyst promoted the formation of toluene and benzene as hydrogenolysis by-products. Reaction kinetics was subjected to a Hammett treatment and the reaction constant (ρ = 0.9) was found to be consistent with a nucleophilic mechanism. A solvent (alcohol, water and alcohol + water) effect is demonstrated and ascribed to competitive adsorption where solvation by polar (water) facilitates benzaldehyde activation. Graphic Abstract

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