2-aminobenzyl Alcohol Research Articles

Novel benzoxazine-based aglycones block glucose uptake in vivo by inhibiting glycosidases.

Glycoside hydrolases catalyze the selective hydrolysis of glycosidic bonds in oligosaccharides, polysaccharides, and their conjugates. β-glucosidases occur in all domains of living organisms and constitute a major group among glycoside hydrolases. On the other hand, the benzoxazinoids occur in living systems and act as stable β-glucosides, such as 2-(2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one)-β-D-gluco-pyranose, which hydrolyse to an aglycone DIMBOA. Here, we synthesized the library of novel 1,3-benzoxazine scaffold based aglycones by using 2-aminobenzyl alcohols and aldehydes from one-pot reaction in a chloroacetic acid catalytic system via aerobic oxidative synthesis. Among the synthesized benzoxazines, 4-(7-chloro-2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)phenol (compound 7) exhibit significant inhibition towards glucosidase compared to acarbose, with a IC50 value of 11.5 µM. Based upon results generated by in silico target prediction algorithms (Naïve Bayesian classifier), these aglycones potentially target the additional sodium/glucose cotransporter 1 (where a log likelihood score of 2.70 was observed). Furthermore, the in vitro glucosidase activity was correlated with the in silico docking results, with a high docking score for the aglycones towards the substrate binding site of glycosidase. Evidently, the in vitro and in vivo experiments clearly suggest an anti-hyperglycemic effect via glucose uptake inhibition by 4-(7-chloro-2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)phenol in the starved rat model. These synthetic aglycones could constitute a novel pharmacological approach for the treatment, or re-enforcement of existing treatments, of type 2 diabetes and associated secondary complications.

Simple grinding-induced reactions of 2-aminobenzyl alcohol and benzaldehyde derivatives, a rapid synthetic route to 3,1-benzoxazines

The grinding-induced reactions of 2-aminobenzyl alcohol and benzaldehyde derivatives in the presence of 30 mol% of acetic acid to give 3,1-benzoxazines are described. The reactions were performed at room temperature affording 3,1-benzoxazines in yields above 95% and high purity when benzaldehyde and its chloro and nitro derivatives were used. KEY WORDS: 2-Aminobenzyl alcohol, Benzaldehyde, Acetic acid, 3,1-Benzoxazines Bull. Chem. Soc. Ethiop. 2014, 28(2), 301-304.DOI: http://dx.doi.org/10.4314/bcse.v28i2.14

The Role of Aromatic Schiff Bases in the Dyes Techniques

Anil compounds are Schiff bases derived from aniline moiety containing phenyl or substituted phenyl group, which sometimes called Azo dyes. These Schiff bases can be directly prepared from aromatic amine with aromatic carbonyl groups, which are stable and can be manipulated under different and suitable conditions. The phenomena of coordination of Schiff bases with metal ions give the Schiff bases the good advantages to be introduced in the dyes synthesis. The classification of dyes is based on the chemical structure or on the basis of the chromophoric system. The metal complex dyes are combinations of dyestuff and metal ions, in which the coordination complex can be applied or used to be improvement factors in dye techniques. The investigation and the characterization of the resulted dyes were performed by using different physical techniques. The produced dyes were applied to different fibres, such as sheep wool and goat hair with two Schiff bases synthesised from salicylaldehyde either with 2-aminophenol or 2-aminobenzyl alcohol. Also the investigation includes the effect of mordant type on the dyeing process.

Palladium catalyzed acetoxylation of benzylic C–H bonds using a bidentate picolinamide directing group

A general palladium catalyzed acetoxylation of benzylic C-H bonds has been developed. Picolinamides serve as an excellent directing group for the C-H activation of benzylic methyls. A wide range of 2-amino benzyl alcohol analogues were synthesized in good yields. The products demonstrated broad synthetic utilities toward various benzo-fused heterocycles. Mechanistic studies revealed the key rate-limiting C-H insertion step, which could be affected by the substitution pattern of the parent arene.

ChemInform Abstract: Three‐Component Tandem‐Intramolecular Hydroamination Reactions in One Pot Involving Indoles, 2‐Aminobenzyl Alcohols, and 2‐Alkynylbenzaldehydes: Consecutive 7‐endo‐trig and Electrophilic 6‐endo‐dig Cyclizations.

A one-pot protocol for the synthesis of indole-based annulated polyheterocycles involving consecutive 7-endo-trig and electrophilic 6-endo-dig cyclizations is described. The reaction proceeds initially through annulation of 5-methoxyindole, 2-amino benzyl alcohol and 2-alkynylbenzaldehyde

An open metal site metal–organic framework Cu(BDC) as a promising heterogeneous catalyst for the modified Friedländer reaction

A crystalline porous metal–organic framework Cu(BDC) was synthesized, and characterized by several techniques, including X-ray powder diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR), atomic absorption spectrophotometry (AAS), hydrogen temperature-programmed reduction (H2-TPR), and nitrogen physisorption measurements. The Cu(BDC) exhibited high catalytic activity for the modified Friedländer transformation using 2-aminobenzyl alcohol as the starting material, thus offering advantages over the conventional Friedländer reaction in terms of avoiding the problems associated with the storage of the highly unstable 2-aminobenzaldehyde. Moreover, the Cu(BDC) could offer significantly higher catalytic activity than that of other Cu-MOFs such as Cu3(BTC)2, Cu(BPDC), and Cu2(BDC)2(DABCO). The catalyst could be recovered and reused several times without a significant degradation in catalytic activity. The modified Friedländer reaction could only occur in the presence of the solid Cu(BDC) with no contribution from leached active species.

ChemInform Abstract: Palladium‐Based Nanocatalyst for One‐Pot Synthesis of Polysubstituted Quinolines.

The synthesis of quinolines has been achieved through a one-pot, two-step tandem reaction catalyzed with AgPd alloy nanoparticles supported on carbon. AgPd alloy nanoparticles catalyzed the coupling of a ketone with a primary alcohol through a hydrogen autotransfer process, which yields α-alkylated ketones under an Ar flow. These are reacted with 2-aminobenzyl alcohols in a modified Friedlander synthesis to give polysubstituted quinolines in moderate to good yields.

Reactions of 1,5-diketones with 2-aminobenzyl alcohol and 2-aminomethylaniline and behavior of the products in oxidative coupling

Reactions of some 1,5-diketones with 2-aminobenzyl alcohol and 2-aminomethylaniline follow double cyclization scheme with formation of pyridobenzoxazine and pyridoquinazoline derivatives, respectively. Oxidative coupling of the cyclization products with CH acids occurs at the 4-position of the pyridine ring.

ChemInform Abstract: CuCl/DABCO/4‐HO‐TEMPO‐Catalyzed Aerobic Oxidative Synthesis of 2‐Substituted Quinazolines and 4H‐3,1‐Benzoxazines.

The Cu/N-ligand/TEMPO catalytic system was first applied to the aerobic oxidative synthesis of heterocycles. As demonstrated, 2-substituted quinazolines and 4H-3,1-benzoxazines were synthesized efficiently from the one-pot reaction of aldehydes with 2-aminobenzylamines and 2-aminobenzyl alcohols, respectively, by employing CuCl/DABCO/4-HO-TEMPO as the catalysts and oxygen as the terminal oxidant.

CuCl/DABCO/4-HO-TEMPO-Catalyzed Aerobic Oxidative Synthesis of 2-Substituted Quinazolines and 4H-3,1-Benzoxazines

The Cu/N-ligand/TEMPO catalytic system was first applied to the aerobic oxidative synthesis of heterocycles. As demonstrated, 2-substituted quinazolines and 4H-3,1-benzoxazines were synthesized efficiently from the one-pot reaction of aldehydes with 2-aminobenzylamines and 2-aminobenzyl alcohols, respectively, by employing CuCl/DABCO/4-HO-TEMPO as the catalysts and oxygen as the terminal oxidant.

ChemInform Abstract: A Concise and Cascade Synthesis of Batracylin and Substituted Isoindolo[1,2‐b]quinazolin‐12(10H)‐ones.

AbstractThe synthesis of the title skeleton is readily achieved through a cascade cyclization of 2‐cyanomethyl benzoate with aminobenzyl alcohols.

Direct annulation and alkylation of indoles with 2-aminobenzyl alcohols catalyzed by TFA

An efficient method for the annulation of indoles with 2-aminobenzyl alcohols, catalyzed by TFA, to furnish 5,6-fused indoline aminals is reported. This method can be extended to the alkylation of indoles at C3. 2-Aminobenzyl alcohols are used directly without recourse to protection of the aniline nitrogen or activation of the alcohol.

Synthesis and Anticancer Activity of New 2‐Aryl‐4H‐3,1‐benzothiazines

New compounds of 2-aryl-4H-3,1-benzothiazine set were synthesized and tested for their antiproliferative activity as part of our research in the antitumor field. The title compounds were obtained by the reaction of aryl-modified sulfinylbis((2,4-dihydroxyphenyl)methanethione) with 2-aminobenzyl alcohols. The reaction proceeded through thiobenzanilide intermediates, which were converted to the 4H-3,1-benzothiazine fused ring by an endocyclization process. The structures of compounds were identified from elemental, IR, (1) H-NMR, (13) C-NMR, and MS spectra analyses. The cytotoxicity in vitro against four human cancer cell lines was determined. The antiproliferative properties of some compounds were more beneficial than cisplatin studied comparatively.

A recyclable copper catalysis in modified Friedländer quinoline synthesis

2-Aminobenzyl alcohol reacts with ketones in dioxane at 100 °C in the presence of a catalytic amount of a copper catalyst along with KOH and MS 4A under O 2 atmosphere to afford the corresponding quinolines in good yields. The catalytic system could be recovered and reused 10 times without any loss of catalytic activity. A similar catalytic system using copper catalyst/PEG-2000 is also effective for this coupling and cyclization with a similar catalytic potential. 2-Aminobenzyl alcohol is also coupled and cyclized with secondary alcohols under the CuCl 2/MS 4A catalytic system to give quinolines in moderate to good yields.

Synthesis and properties of the copolymers based on aniline and 2-aminobenzyl alcohol

A kind of novel conducting copolymer with different compositions based on aniline and 2-aminobenzyl alcohol was prepared by chemical oxidative polymerization method. The copolymers were characterized by the methods of FT-IR, UV–Vis, XRD and DSC. It indicated that 2-aminobenzyl alcohol could copolymerize with aniline by this method. In addition, the solubility and conductivity of the copolymers were also studied in detail. The results showed that the copolymers had better solubility in pyridine than pure HCl doped polyaniline and the conductivities were decreased with the increase of the molar ratio of 2-aminobenzyl alcohol in copolymer.

ChemInform Abstract: Green Approaches to Highly Selective Processes: Reactions of Dimethyl Carbonate over Both Zeolites and Base Catalysts

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A recyclable palladium-catalyzed modified Friedländer quinoline synthesis

2-Aminobenzyl alcohol reacts with an array of ketones in toluene/poly(ethylene glycol) (PEG-2000) at 100 °C in the presence of a palladium catalyst along with KOH under an atmosphere of air to give the corresponding quinolines in good yields. The catalytic system could be recovered and reused five times without any loss of catalytic activity.

Green approaches to highly selective processes: Reactions of dimethyl carbonate over both zeolites and base catalysts

Abstract Nowadays available by clean industrial processes, dimethyl carbonate (DMC) possesses properties of nontoxicity and biodegradability which make it a true green reagent/solvent to devise syntheses that prevent pollution at the source. In particular, the versatile reactivity of DMC allows both methylation and carboxymethylation protocols that can replace conventional and highly noxious reagents such as methyl halides (and dimethyl sulfate, DMS) and phosgene. In the field of DMC-mediated methylations, representative examples are the reactions of DMC with CH2-active compounds and primary aromatic amines. In the presence of organic/inorganic bases or zeolites (faujasites) catalysts, these processes proceed with unprecedented selectivity (up to 99 %, at complete conversion) toward the corresponding mono-C- and mono-N-methyl derivatives, a result hitherto not possible with conventional alkylation reagents. In the case of ambident amines (e.g., aminophenols, aminobenzyl alcohols, aminobenzoic acids, and aminobenzamides), the unique combination of DMC and zeolites allows not only a very high mono-N-methyl selectivity, but also a complete chemoselectivity toward the amino group. The other nucleophilic functionalities (OH, CO2H, CH2OH, CONH2) are fully preserved from alkylation and/or transesterification reactions, usually observed over basic catalysts.

A copper(II)-catalyzed protocol for modified Friedländer quinoline synthesis

2-Aminobenzyl alcohol reacts with an array of ketones in dioxane at 100 °C in the presence of a catalytic amount of CuCl 2 along with KOH under O 2 atmosphere to afford the corresponding quinolines in good yields. 2-Aminobenzyl alcohol is also oxidatively coupled and cyclized with various aldehydes by step-by-step procedure, an initial treatment of 2-aminobenzyl alcohol in the presence of CuCl 2 and KOH in dioxane under O 2 atmosphere and subsequent addition of aldehyde to the mixture followed by stirring under argon atmosphere, to give 3-substituted quinolines in moderate to good yields.

RuCl 2(DMSO) 4 catalyzes the β-alkylation of secondary alcohols with primary alcohols through a hydrogen autotransfer process

The electrophilic β-alkylation of secondary alcohols with primary alcohols is accomplished by a hydrogen autotransfer process catalyzed by RuCl 2(DMSO) 4. The reaction can produce either simple alkylated secondary alcohols or α,β-unsaturated ketones with good to excellent results just by choosing the appropriate starting secondary alcohol (methyl or longer chain secondary alcohol, respectively), as well as quinolines (by using 2-aminobenzyl alcohol).