53012-61-6

Usage

Chemical Properties

clear yellow liquid

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 2972, 1978 DOI: 10.1021/jo00409a008

InChI:InChI=1/C9H9NO/c1-6-3-4-8-9(5-6)11-7(2)10-8/h3-5H,1-2H3

Upstream product

• 62103-86-0 3,7-dimethyl-2H-benz[b][1,4]oxazin-2-one 
• 101010-07-5 C₁₃H₁₀F₆NO₅Tl 
• 18931-78-7 N-(2-chloro-4-methylphenyl)acetamide 
• 615-65-6 2-chloro-4-methyl-benzenamine 
• 25172-51-4 1-(2-hydroxy-4-methyl-phenyl)-ethanone oxime 
• 614-83-5 2-bromo-4-methylacetanilide 
• 2835-98-5 2-Hydroxy-4-methylanilin 
• 78-39-7 Triethyl orthoacetate 
• 123-54-6 acetylacetone 
• 6921-64-8 4'-hydroxy-2'-methylacetophenone 
• 127-19-5 N,N-dimethyl acetamide 
• 75-05-8 acetonitrile 
• 108-24-7 acetic anhydride 
• 583-68-6 2-bromo-p-toluidine 

Downstream Products

• 65965-21-1 2-{4-[2-(6-methyl-benzooxazol-2-yl)-vinyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridine 
• 61519-87-7 6-methyl-2-[4-(4-phenyl-[1,2,3]triazol-2-yl)-styryl]-benzooxazole 
• 61519-85-5 6-methyl-2-[4-(2-phenyl-2H-[1,2,3]triazol-4-yl)-styryl]-benzooxazole 

Relevant academic research and scientific papers

Hydrogen-bond-supported dimeric boron complexes of potentially tetradentate β-diketiminate ligands

Two dimeric boron complexes of potentially tetradentate and trianionic β-diketiminate ligands bearing phenol substituents were prepared and characterized. The synthetic routes employed were designed to circumvent the undesirable formation of β-ketimines and 2-methylbenzoxazoles observed when traditional synthetic routes toward the target β-diketiminate ligands were attempted. The title complexes were isolated via demethylation of β-diketimine ligands and boron difluoride complexes bearing 2-anisole N-aryl substituents using boron tribromide. The resulting complexes were found to contain a unique hydrogen-bond-supported boron-oxygen-boron bridge, as confirmed by X-ray crystallography. The stability of the resulting dimeric structures relative to the corresponding monomeric, tetradentate boron complexes was studied computationally, and theory confirmed that the dimeric structures were strongly favored. The absorption spectra of the dimers were red-shifted relative to the parent β-diketimine ligands. The complexes were irreversibly oxidized and reduced electrochemically and were weakly emissive at low concentrations (Stokes shifts between 23 and 31 nm), showing little solvent dependence.

Synthesis method of 2-substituted benzoxazole, 2-substituted benzothiazole and derivatives thereof

The invention provides a synthesis method of 2-substituted benzoxazole, 2-substituted benzothiazole and derivatives thereof. In the method, through ortho-aminophenol/2-aminothiophenol cyclization catalyzed by imidazole hydrochloride, synthesis of functionalized 2-substituted benzoxazole and 2-substituted benzothiazole is realized; the method is simple, economical and high in practicality. No othercatalysts or additives are used, the synthesis method ensures good functional group tolerance and excellent yield and purity, the reaction time is short, no harsh reaction conditions are needed, andthe method is suitable for industrial production.

Synthesis of Highly Functionalized N,N-Diarylamides by an Anodic C,N-Coupling Reaction

We report an innovative, sustainable and straightforward protocol for the synthesis of N,N-diarylamides equipped with nonprotected hydroxyl groups by using electrosynthesis. The concept allows the application of various substrates furnishing diarylamides with yields up to 57 % within a single and direct electrolytic protocol. The method is thereby easy to conduct in an undivided cell with constant current conditions offering a versatile and short-cut alternative to conventional pathways.

Eco-friendly syntheses of 2-substituted benzoxazoles and 2-substituted benzothiazoles from 2-aminophenols, 2-aminothiophenols and DMF derivatives in the presence of imidazolium chloride

A simple, economical and metal-free approach to the synthesis of 2-substituted benzoxazoles and 2-substituted benzothiazoles from 2-aminophenols, 2-aminothiophenols and DMF derivatives, only using imidazolium chloride (50% mmol) as promoter without any other additive, was reported. Various 2-substituted benzoxazoles and 2-substituted benzothiazoles were thus prepared in moderate to excellent yields.

PHARMACEUTICAL COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS

Complement Factor D inhibitors, pharmaceutical compositions, and uses thereof, as well as processes for their manufacture are provided. The compounds provided include Formula I, Formula II, Formula III, and Formula IV or a pharmaceutically acceptable salt, prodrug, isotopic analog, N-oxide, or isolated isomer thereof, optionally in a pharmaceutically acceptable composition. The inhibitors described herein target Factor D and inhibit or regulate the complement cascade.

Ligand-promoted, copper nanoparticles catalyzed one-pot synthesis of substituted benzoxazoles from 2-bromoanilines and acyl chlorides

A facile, highly efficient, and practical one-pot synthetic strategy for benzoxazoles was developed by using copper nanoparticles as a catalyst with o-bromoanilines and acyl chlorides as starting materials. With the promotion of 1,10-phenanthroline ligand, the copper nanoparticles catalyst showed highly catalytic activity under mild conditions. This methodology is tolerant of a wide variety of functional groups and gives good to excellent yields in most examples. Furthermore, the solid catalyst could be recovered and reused conveniently several times with satisfactory yields.

Acid Catalyzed Direct-Amidation-Dehydrocyclization of 2-Hydroxy-acetophenones to Benzoxazoles by a One-Pot Sustainable Synthesis

A series of 2-methyl-benzoxazoles have been synthesized starting from 2-hydroxy-acetophenones via a one-pot three steps reaction. Hydroxylamonium salt has been used as amidation agent. The reaction occurs with different anions, but the best results is achieved with hydroxylamonium hydrchloride. Despite the number of consecutive stages, the reaction is highly selective. Mild reaction conditions and various solvents can be used, but trifluoroacetic acid is the preferred. Almost, complete recovery of the trifluoroacetic acid can be achieved by vacuum distillation. The role of trifluoroacetic acid, as well as, of the hydroxylamonium salt suggests a cooperative effect leading to high selective formation of 2-methyl-benzoxazoles. Graphical Abstract: One-pot TFA catalyzed synthesis of benzoxazoles starting from 2-hydroxyacetophenones. (Chemical Equation Presented).

Synthesis of benzoxazoles from 2-aminophenols and β-diketones using a combined catalyst of br?nsted acid and copper iodide

Cyclization reactions of 2-aminophenols with β-diketones catalyzed by a combination of Br?nsted acid and CuI are presented. Various 2-substituted benzoxazoles were obtained through these reactions. Different substituents such as methyl, chloro, bromo, nitro, and methoxy on 2-aminophenol are tolerated under the optimized reaction conditions.

The efficient o-benzenedisulfonimide catalysed synthesis of benzothiazoles, benzoxazoles and benzimidazoles

O-Benzenedisulfonimide has been used to efficiently catalyse the reaction between 2-aminothiophenol, 2-aminophenol, o-phenylenediamine and various ortho esters (28 examples; average yield 90%) or aldehydes (17 examples; average yield 72%) giving the corresponding benzofused azoles in excellent yields. Reaction conditions were very simple. In addition, other carboxylic acid derivatives have been tested and gave good results. The catalyst was easily recovered and reused. ARKAT-USA, Inc.