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Uses

N-Acylbenzotriazoles from Aldrich: Neutral Acylating Reagents

InChI:InChI=1/C13H9N3O/c17-13(10-6-2-1-3-7-10)16-12-9-5-4-8-11(12)14-15-16/h1-9H

Upstream product

• 123-91-1 1,4-dioxane 
• 110-86-1 pyridine 
• 28539-02-8 1-Hydroxymethyl-1H-benzotriazole 
• 98-88-4 benzoyl chloride 
• 721-47-1 2'-Aminobenzanilid 
• 95-14-7 1,2,3-Benzotriazole 
• 18039-42-4 5-Phenyl-1H-tetrazole 
• 43183-36-4 1-(trimethylsilyl)-1H-benzotriazole 
• 463-58-1 carbon oxide sulfide 
• 100-58-3 phenylmagnesium bromide 
• 117632-84-5 1-((trifluoromethyl)sulfonyl)-1H-benzo[d][1,2,3]triazole 
• 203070-24-0 1-(Phenyl-bis-phenylselanyl-methyl)-1H-benzotriazole 
• 37073-15-7 1-(methanesulfonyl)-1H-1,2,3-benzotriazole 
• 65-85-0 benzoic acid 

Downstream Products

• 155896-88-1 Allyl 2-O-Benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 1671-75-6 Heptanophenone 
• 93-55-0 1-phenyl-propan-1-one 
• 127446-71-3 Allyl 2,6-di-O-benzoyl-α-D-glucopyranoside 
• 122479-76-9 trideuteriomethyl O-(6-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-mannopyranoside 
• 93-98-1 N-phenyl benzoyl amide 
• 908554-54-1 N-(2-isopropoxyphenyl)benzamide 
• 55-21-0 benzamide 
• 65-85-0 benzoic acid 
• 95-14-7 1,2,3-Benzotriazole 
• 7404-97-9 2-(benzoylamino)biphenyl 
• 1614-15-9 N,N-bis-benzotriazole 
• 833-50-1 2-phenylbenzo[d]oxazole 
• 2782-40-3 N-butylbenzamide 

Relevant academic research and scientific papers

N -Acylbenzotriazoles as Proficient Substrates for an Easy Access to Ureas, Acylureas, Carbamates, and Thiocarbamates via Curtius Rearrangement Using Diphenylphosphoryl Azide (DPPA) as Azide Donor

A diverse range of ureas, N -acylureas, carbamates, and thiocarbamates has been synthesized in good to excellent yields by reacting N -acylbenzotriazoles individually with amines or amides or phenols or thiols in the presence of diphenylphosphoryl azide (DPPA) as a suitable azide donor in anhydrous toluene at 110 °C for 3-4 hours. In this route, DPPA was found to be a good alternative to trimethylsilyl azide and sodium azide for the azide donor in Curtius degradation. The high reaction yields, one-pot and metal-free conditions, straightforward nature, easy handling, use of readily available reagents, and in many cases avoidance of column chromatography are the notable features of the devised protocol.

N-Acylbenzotriazole: convenient approach for protecting group-free monoacylation of symmetric diamines

Abstract: An efficient green route for monoacylation of aromatic diamines, namely o-phenylenediamine and p-phenylenediamine and aliphatic diamines ethylenediamine and piperazine using N-acylbenzotriazoles (NABs) in n-butanol was developed. The new protocol does not require prior selective protection of the diamine and comprises simple conditions, short reaction times, an easy work up as well as high isolated yields (69–94%). Moreover, the method described herein enable stepwise acylation of aliphatic diamines such as ethylenediamine and piperazine with two different N-acylbenzotriazoles affording unsymmetrical substituted diamines that can be used for construction of pharmaceutically important targets such as drugs, foldamers, and drug conjugates. Graphic abstract: [Figure not available: see fulltext.]

Synthesis, assessment and corrosion protection investigations of some novel peptidomimetic cationic surfactants: Empirical and theoretical insights

Three novel peptidomimetic cationic surfactants were synthesized in good yields. The chemical configurations of these surfactants were clarified using 1H, 13C NMR and FT-IR spectroscopy. The inhibition capacity and adsorption performance of these compounds on C-steel were studied by electrochemical techniques (Electrochemical impedance spectroscopy (EIS) and Potentiodynamic polarization (PDP) methods). The prepared compounds demonstrated outstanding protection power for the erosion of C-steel in 0.5 M HCl at 323 K. The PDP studies demonstrated that the novel surfactants behaved as mixed-type additives. The protection capacity rises with an increasing surfactant dose, with values ranging from 93.10 to 98.25percent at 100 ppm. The adsorption of additives on the electrode interface follows the Langmuir model and contains chemisorption modes. The Monte Carlo (MD) simulations and density functional theory (DFT) calculations support the experimental findings and provide insight into the understanding of the adsorption features and protection performance mechanisms of the examined surfactants.

Discovery of the first Mycobacterium tuberculosis MabA (FabG1) inhibitors through a fragment-based screening

Mycobacterium tuberculosis (M.tb), the etiologic agent of tuberculosis, remains the leading cause of death from a single infectious agent worldwide. The emergence of drug-resistant M.tb strains stresses the need for drugs acting on new targets. Mycolic acids are very long chain fatty acids playing an essential role in the architecture and permeability of the mycobacterial cell wall. Their biosynthesis involves two fatty acid synthase (FAS) systems. Among the four enzymes (MabA, HadAB/BC, InhA and KasA/B) of the FAS-II cycle, MabA (FabG1) remains the only one for which specific inhibitors have not been reported yet. The development of a new LC-MS/MS based enzymatic assay allowed the screening of a 1280 fragment-library and led to the discovery of the first small molecules that inhibit MabA activity. A fragment from the anthranilic acid series was optimized into more potent inhibitors and their binding to MabA was confirmed by 19F ligand-observed NMR experiments.

Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2-Aryldiamines

An operationally simple method has been developed for the preparation of N-unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2-aryldiamines under mild conditions, using a polymer-supported nitrite reagent and p-tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N-alkyl, -aryl, and -acyl ortho-aminoanilines leading to the synthesis of N1-substituted benzotriazoles. The synthetic utility of this one-pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α-amino acid analogue.

Tert -Butyl nitrite promoted transamidation of secondary amides under metal and catalyst free conditions

A mild and efficient method is demonstrated for the transamidation of secondary amides with various amines including primary, secondary, cyclic and acyclic amines in the presence of tert-butyl nitrite. The reaction proceeds through the N-nitrosamide intermediate and provides the transamidation products in good to excellent yields at room temperature. Moreover, the developed methodology does not require any catalyst or additives.

Trichloroisocyanuric Acid Mediated High-Yielding Synthesis of N -Acylbenzotriazoles under Mild Reaction Conditions

N -Acylbenzotriazoles are achieved in good yields from the corresponding carboxylic acids by using only 0.35 equivalent of trichloroisocyanuric acid and 1.2 equivalents of PPh 3. The salient features of the developed reaction path include an ec

An Improved N-Acylation of 1 H-Benzotriazole Using 2,2′-Dipyridyl?-di?-sulfide and Triphenylphosphine

A novel path has been developed for the conversion of carboxylic acids into the corresponding N-acylbenzotriazoles by using 2,2′-dipyridyl disulfide/PPh 3 in anhydrous dichloromethane in the presence of 1 H-benzotriazole. Mild reaction conditio

Synthesis of benzotriazoles derivatives and their dual potential as α-amylase and α-glucosidase inhibitors in vitro: Structure-activity relationship, molecular docking, and kinetic studies

Benzotriazoles (4–6) were synthesized which were further reacted with different substituted benzoic acids and phenacyl bromides to synthesize benzotriazole derivatives (7–40). The synthetic compounds (7–40) were characterized via different spectroscopic techniques including EI-MS, HREI-MS, 1H-, and 13C NMR. These molecules were examined for their anti-hyperglycemic potential hence were evaluated for α-glucosidase and α-amylase inhibitory activities. All benzotriazoles displayed moderate to good inhibitory activity in the range of IC50 values of 2.00–5.6 and 2.04–5.72 μM against α-glucosidase and α-amylase enzymes, respectively. The synthetic compounds were divided into two categories “A” and “B”, in order to understand the structure-activity relationship. Compounds 25 (IC50 = 2.41 ± 1.31 μM), (IC50 = 2.5 ± 1.21 μM), 36 (IC50 = 2.12 ± 1.35 μM), (IC50 = 2.21 ± 1.08 μM), and 37 (IC50 = 2.00 ± 1.22 μM), (IC50 = 2.04 ± 1.4 μM) with chloro substitution/s at aryl ring were found to be most active against α-glucosidase and α-amylase enzymes. Molecular docking studies on all compounds were performed which revealed that chloro substitutions are playing a pivotal role in the binding interactions. The enzyme inhibition mode was also studied and the kinetic studies revealed that the synthetic molecules have shown competitive mode of inhibition against α-amylase and non-competitive mode of inhibition against α-glucosidase enzyme.