58523-78-7

Upstream product

• 273-53-0 benzoxazole 
• 106-49-0 p-toluidine 
• 2382-96-9 2-sulfanyl-1,3-benzoxazole 
• 16634-82-5 N-(p-tolyl)-2-chloroacetamide 
• 615-18-9 2-chloro-1,3-benzoxazole 
• 95-55-6 2-amino-phenol 
• 75-15-0 carbon disulfide 
• 4570-41-6 1,3-benzoxazol-2-amine 
• 106-38-7 para-bromotoluene 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 14223-45-1 p-tolyl isoselenocyanate 

Relevant academic research and scientific papers

Microwave-assisted hydrogen peroxide-mediated synthesis of benzoxazoles and related heterocycles via cyclodesulfurization

A novel approach has been developed to construct benzoxazoles and similar N- and S-containing heterocycles from their corresponding isothiocyanates and o-substituted anilines via cyclodesulfurization. The reaction was found to proceed via in situ formatio

Environment-friendly and efficient synthesis of 2-aminobenzo-xazoles and 2-aminobenzothiazoles catalyzed by: Vitreoscilla hemoglobin incorporating a cobalt porphyrin cofactor

In this study, an environment-friendly and efficient artificial Vitreoscilla hemoglobin (VHb) for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles has been reported. We demonstrate an expression-based porphyrin substitution strategy to produce VHb containing cobalt porphyrin instead of native hemin, which can catalyze the oxidative cyclization of corresponding 2-aminobenzoxazoles and 2-aminobenthiazoles with up to 97% yield and 4850 catalytic turnovers in water under aerobic conditions. Hence, we provide a green and mild method for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles. In addition, we indicate the value of porphyrin ligand substitution as a strategy to tune and enhance the catalytic properties of hemoproteins in non-natural reactions.

Application of cuprous complex containing ortho-position carborane Schiff base ligand

The invention relates to an application of a cuprous complex containing an ortho-position carborane Schiff base ligand, and a structural formula of the cuprous complex is shown in the specification, in the formula, Ar is aryl containing a benzene ring or heterocyclic aryl, and . is a boron hydrogen bond; the cuprous complex is used for catalyzing an oxidative coupling reaction of benzoxazole and amine compounds to synthesize 2-amino benzoxazole derivatives. The preparation method specifically comprises the following steps: dissolving a cuprous complex, benzoxazole and an amine compound in an organic solvent, then reacting with an oxidant at 50-80 DEG C for 6-12 hours, and separating and purifying to obtain the 2-amino benzoxazole derivative. Compared with the prior art, the cuprous complexcontaining the ortho-carborane Schiff base ligand can efficiently catalyze oxidative coupling of benzoxazole and primary amine or secondary amine to synthesize the 2-amino benzoxazole derivative; theproduct has the advantages of good selectivity, low catalyst dosage, mild reaction conditions, high reaction rate, high yield, wide substrate range and the like, and shows a wide industrial application prospect.

A Cu2O/TBAB-promoted approach to synthesize heteroaromatic 2-Amines: Via one-pot cyclization of aryl isothiocyanates with ortho-substituted amines in water

An efficient approach to synthesize heteroaromatic 2-Amines from one-pot desulfurization/dehydrogenative cyclization of aryl isothiocyanates with ortho-substituted amines in water was developed. This approach tolerated a wide range of functional groups on

One-pot reaction for the synthesis of N-substituted 2-aminobenzoxazoles using triphenylbismuth dichloride as cyclodesulfurization reagent

The treatment of various 2-aminophenols with isothiocyanates afforded thioureas, which were reacted in situ with triphenylbismuth dichloride in the presence of triethylamine to give the expected N-substituted benzoxazol-2-amines in good to excellent yields. Triphenylbismuth dichloride promoted the successful cyclodesulfurization of thioureas with short reaction times under mild reaction conditions. This reaction is the first example of the synthesis of heterocyclic rings using a pentavalent organobismuth reagent.

Microwave-Enhanced On-Water Amination of 2-Mercaptobenzoxazoles to Prepare 2-Aminobenzoxazoles

In this work, we developed a catalyst-free amination of 2-mercaptobenzoxazoles on water under microwave irradiation. The product, 2-aminobenzoxazoles, was successfully produced via direct amination with various amines in moderate to high yields. The formal synthesis of Suvorexant, a medication for the treatment of insomnia, was accomplished using a developed amination process. The reaction was completed in an hour at 100-150 °C in a microwave reactor without the use of external catalyst or additive. Key benefits of this process include an on-water reaction, short reaction time, being scalable and catalyst-free, and use of 2-mercaptobenzoxazoles as an inexpensive starting material having low environmental impact in its preparation.

Synthesis of N-aryl-2-aminobenzoxazoles from substituted benzoxazole-2-thiol and 2-chloro-N-arylacetamides in KOH-DMF system

A simple and novel method for the synthesis of N-aryl-2-aminobenzoxazoles from substituted benzoxazole-2-thiol and 2-chloro-N-arylacetamides in KOH-DMF system has been developed. The present protocol provides an attractive approach to access various N-aryl-2-aminobenzoxazoles in moderate to good yields without using transition metal catalyst under very mild reaction condition.

Synthesis, biological evaluation and molecular docking study of N-arylbenzo[d]oxazol-2-amines as potential α-glucosidase inhibitors

A novel series of N-arylbenzo[d]oxazol-2-amines (4a–4m) were synthesized and evaluated for their α-glucosidase inhibitory activity. Compounds 4f–4i, 4k and 4m displayed potent inhibitory activity against α-glucosidase with IC50values in the range of 32.49?±?0.17–120.24?±?0.51?μM as compared to the standard drug acarbose. Among all tested compounds, compound 4g having 4-phenoxy substitution at the phenyl ring was found to be the most active inhibitor of α-glucosidase with an IC50value of 32.49?±?0.17?μM. Analysis of the kinetics of enzyme inhibition indicated that compound 4g is a noncompetitive inhibitor of α-glucosidase with a Kivalue of 31.33?μM. Binding interaction of compound 4g with α-glucosidase was explored by molecular docking simulation.

Straightforward synthesis of 2-anilinobenzoxazoles and -benzothiazoles via mechanochemical ball-milling-promoted one-pot reactions

Under mechanochemical ball-milling and solvent-free conditions, a series of 2-anilinobenzoxazoles and -thiazoles were synthesized directly from the one-pot reaction of anilines, CS2, and 2-aminophenol and -thiophenol. This protocol exhibits the

Direct amination of azoles using CuCl2 complexes of amines under mild conditions

The efficient direct amination of azoles, including benzoxazole, benzothiazole and 1-methylbenzimidazole, was accomplished in moderate to good yields using CuCl2 complexes of amines as a readily available and effective nitrogen source. The coupling reactions were performed under mild conditions: at 30-50°C within 3-6 h, in air without oxidant, additive, ligand and anhydrous conditions.