3164-11-2

Upstream product

• 273-53-0 benzoxazole 
• 89-75-8 2,4-dichlorobenzoyl chloride 
• 95-55-6 2-amino-phenol 
• 95-00-1 2,4-dichloro-benzenemethanamine 
• 72755-08-9 N-methoxy-2,4-dichlorobenzamide 
• 50-84-0 2,4 dichlorobenzoic acid 
• 19918-03-7 N-<2,4-Dichlor-benzyliden>-2-hydroxy-anilin 
• 874-42-0 2,4-dichlorobenzaldeyhde 

Downstream Products

• 142629-38-7 2-(o,p-Di-phenoxyphenyl)benzoxazole 
• 126843-23-0 6-chloro-2-(2,4-dichlorophenyl)benzoxazole 
• 1325241-72-2 6-bromo-2-(2,4-dichlorophenyl)benzoxazole 

Relevant academic research and scientific papers

Syntheses, characterization, and catalytic potential of novel vanadium and molybdenum Schiff base complexes for the preparation of benzimidazoles, benzoxazoles, and benzothiazoles under thermal and ultrasonic conditions

A new ONO-tridentate Schiff base ligand (H2L) derived from 3-methoxysalicylaldehyde and nicotinic hydrazide was synthesized and characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR, UV–Vis, and powder XRD studies. Then, oxovanadium(V) and dioxomolybdenum(VI) Schiff base complexes, VOL and MoO2L, were also prepared and characterized by different techniques. Moreover, the catalytic activities of both complexes were investigated for the synthesis of benzimidazoles, benzoxazoles, and benzothiazoles under reflux conditions as well as through ultrasonic irradiation. The results revealed several advantages of this procedure, including high product yields, short reaction times, facile work-up procedure, simplicity in operation, eco-friendly reaction conditions, and green aspects by avoiding toxic catalysts and solvents. Graphic abstract: [Figure not available: see fulltext.]

In-vitro Anti-cancer assay and apoptotic cell pathway of newly synthesized benzoxazole-N-heterocyclic hybrids as potent tyrosine kinase inhibitors

A series of benzoxazole-N-heterocyclic hybrids have been synthesized by a one-pot strategy. Molecular docking study revealed that such compounds have the ability to inhibit enzyme protein tyrosine kinase. The findings of this work have been the successful synthesis of benzoxazole scaffolds, featuring hybrids of benzoxazole with quinoline and quinoxaline respectively. The molecular docking studies have showed these compounds to be inhibitors of tyrosine kinase enzyme which triggers growth of cancer cells. The cytotoxicity study of compounds 4a-f showed better potency against breast cancer cell lines MCF-7 and MDA-MB-231 in contrast to oral and lung cancer cell lines KB and A549. The tyrosine kinase activity was measured using Universal Tyrosine Kinase Assay kit using horseradish peroxide (HRP)-conjugated anti-phosphotyrosine kinase solution as a substrate. The compounds 4c exhibited maximum inhibition in the activity of enzyme tyrosine kinase with IC50 value 0.10 ± 0.16 μM, than other compounds which were studied and thus proved to be inhibitors of enzyme tyrosine kinase. The selective index of all four compounds was found out to be greater than two, indicating the non-toxic behaviour, i.e. good anti-cancer activity. Further, fluorescence microscopic study helped to characterize the mode of cell death, which was found to be late apoptosis as indicated by the orange fluorescence. The SAR analysis has also been carried out.

Palladium(II) Immobilized Onto the Glucose Functionalized Magnetic Nanoparticle as a New and Efficient Catalyst for the One-pot Synthesis of Benzoxazoles

Palladium(II) have been immobilized into the nano magnetic Fe3O4 which was functionalized with glucose in order to achieve a one-pot synthesis of 2-substituted benzoxazole derivatives with high yields in the diverse range of organic solvents. The nano catalyst is highly dispersive in polar solvents and can be easily recovered and reused for 6 runs without significant loss of its activity. Finally, the catalyst was fully characterized by FT-IR, TGA, CHN, SEM, EDX and atomic absorption spectroscopy.

Base-Free Selective O-Arylation and Sequential [3,3]-Rearrangement of Amidoximes with Diaryliodonium Salts: Synthesis of 2-Substituted Benzoxazoles

A variety of functionalized 2-substituted benzoxazoles can be prepared in good yields from amidoximes and diaryliodonium salts by selective O-arylation and sequential [3,3]-rearrangement under metal-free conditions. O-arylation of amidoximes was promoted by 3 ? molecule sieves in the absence of a base and a sequential TFA-mediated [3,3]-rearrangement was used to synthesize 2-substituted benzoxazoles. Both of the O-aryl products and rearrangement products were compatible with a broad range of sensitive functional groups such as ester, aldehyde, nitro, vinyl, amine, and amide groups in addition to halides. A bidentate N-ligand with double benzoxazoles was prepared at gram-scale in two steps. (Figure presented.).

Oxidative Synthesis of Benzimidazoles, Quinoxalines, and Benzoxazoles from Primary Amines by ortho-Quinone Catalysis

The bioinspired ortho-quinone catalysts have been applied to heterocycles synthesis. Without any metal cocatalysts, a sole ortho-quinone catalyst enables the oxidative synthesis of benzimidazoles, quinoxalines and benzoxazoles from primary amines in high yields under mild conditions with oxygen as the terminal oxidant.

A 2 - substituted benzoxazole compound of preparation method (by machine translation)

The invention discloses a method for preparing a 2-substituted benzoxazole compound, and belongs to the technical field of synthesis of benzoxazole compounds. According to the technical scheme, the method is characterized by comprising the steps that an aldehyde compound R1CHO and an ortho-aminophenol compound (please see the specification for the formula) are dissolved in solvent xylene or methylbenzene, and pre-reacting is conducted for one hour when the solvent is heated to be at the temperature of 120 DEG C; then the temperature is lowered to be an indoor temperature, catalyst copper acetylacetonate is added, and negative pressure suction is carried out in the oxygen atmosphere for reacting till TLC monitors that the reacting is complete; filtering is performed, and water and ethyl acetate are added in filter liquor to be extracted; an organic phase is dried through anhydrous sodium sulfate, column chromatography purification is carried out after the solvent is removed by steaming, and accordingly the 2-substituted benzoxazole compound (please see the specification for the formula) is obtained. According to the method, the aldehyde compound and the ortho-aminophenol compound are used as reacting raw materials, the copper acetylacetonate is used as a catalyst, oxygen is used as an oxidizing agent, no extra additives are needed, and a series of 2-substituted benzoxazole compounds are synthesized; operation is simple and practicable, the raw materials are cheap and easy to get, reaction efficiency is high and repeatability is good.

Sonocatalyzed facile synthesis of 2-aryl benzoxazoles using MnO2 nanoparticles as oxidant agent under mild conditions

Nano MnO2 was found to be an efficient oxidant agent for the synthesis of 2-substituted benzoxazoles through one-pot reaction of o-aminophenol and different aromatic aldehydes in acetonitrile under ultrasonic irradiation. This method was performed under mild conditions with high yields, inexpensive and readily available oxidant agent, facile and easy experimental procedure, simple purification of final products, and short reaction times. The prepared nano MnO2 has been characterized by FTIR, XRD, and SEM techniques. The pure products were identified and characterized by physical and spectroscopic data such as; melting point, IR, 1H NMR, and 13C NMR.

Catalyst-free microwave-promoted one pot synthesis of 2-aryl benzoxazoles using MnO2 nanoparticles as a convenient oxidant under mild condition

Abstract: An efficient and facile protocol for one pot synthesis of a series of 2-aryl benzoxazoles through coupling of o-aminophenol with aromatic aldehydes under microwave irradiation in the presence of MnO2 nanoparticles as oxidant reagent was demonstrated. The MnO2 nanoparticles were prepared via a solid-state chemical reaction technique. The structure of oxidant was assigned by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), and scanning electron microscopy (SEM). The target molecules were obtained in good to high yields, high purity and short reaction times. The pure products were identified and characterized by physical and spectral data such as; melting point, IR, 1H NMR and 13C NMR. Graphical Abstract: An efficient and facil protocol for one pot synthesis of a series of 2-aryl benzoxazoles through coupling of o-aminophenol with aromatic aldehydes under microwave irradiation in the precense of MnO2 nanoparticles as oxidant reagent was demonstrated.

KMnO4/HOAc system promoted one-pot synthesis of benzoxazoles from o-aminophenols or oxidative cyclization of o-hydroxyarylidene anilines at room temperature

1,3-Benzoxazoles via oxidative cyclization of corresponding o-hydroxyarylidene anilines was synthesized in the presence of KMnO4/HOAc system. This system also was applied for the one-pot synthesis of 1,3-benzoxazoles from o-amino phenols and aldehydes. The both protocols were processed at room temperature under solvent-free conditions with good to excellent yields.

Microwave Assisted Synthesis of Two-Substituted Benzoxazoles in the Presence of Potassium Cyanide under Mild Conditions

Various two-substituted benzoxazoles were prepared using microwave-assisted reaction of 2-aminophenol with aromatic aldehydes in the presence of one equivalent of potassium cyanide as an equimolecular catalyst. Aldehydes having either electron-donating or withdrawing groups afforded the target products. The important features of this method were high yields, short reaction times and easy work up. The structure of synthesized products was characterized by nuclear magnetic resonance (NMR) and infrared (IR).