21326-84-1

Upstream product

• 36993-70-1 bis(2-benzoxazolyl) disulfide 
• 109-73-9 N-butylamine 
• 2382-96-9 2-sulfanyl-1,3-benzoxazole 
• 95-55-6 2-amino-phenol 
• 592-82-5 butyl isothiocyanate 
• 18430-91-6 1-(2-hydroxyphenyl)pentan-1-one 
• 21160-96-3 butylammonium N-butyldithiocarbamate 
• 2769-64-4 n-butyl isonitrile 
• 273-53-0 benzoxazole 
• 871-71-6 N-butylformamide 
• 2382-96-9 benzo[d]oxazole-2-(3H)-thione 

Relevant academic research and scientific papers

Nucleophilic Substitution at the Guanidine Carbon Center via Guanidine Cyclic Diimide Activation

Despite the electron-deficient nature of the guanidine carbon centers, nucleophilic reactions at these sites have been underdeveloped because of the resonance stabilization of the guanidine group. We propose a guanidine C-N bond substitution strategy entailing the formation of guanidine cyclic diimide (GCDI) structures, which effectively destabilize the resonance structure of the guanidine group. In the presence of acid additives, the guanidine carbon center of GCDIs undergoes nucleophilic substitution reactions with various amines and alcohols.

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

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.

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.

Organocatalytic Visible Light Enabled SNAr of Heterocyclic Thiols: A Metal-Free Approach to 2-Aminobenzoxazoles and 4-Aminoquinazolines

The direct amination reaction of heterocyclic thiols has been developed in the presence of the nonhazardous photocatalyst Rose Bengal under irradiation of visible light. The reaction provides a straightforward approach to pharmaceutically and synthetically useful 2-aminobenzoxazole and 4-aminoquinazoline derivatives from the corresponding heterocyclic thiols with amines in good to excellent yields. Our photochemical reaction can be successfully adapted into a continuous flow reactor which is applicable for large-scale chemical industry. The key benefits of this reaction include the use of metal-free, low-cost Rose Bengal catalyst and practical operation (ambient temperature, open flask, and undried solvents).

Copper-catalyzed direct amination of benzoxazoles using primary amines as nitrogen sources

A facile, efficient, and simple protocol for direct oxidative C-H amination of benzoxazoles with primary amines through copper-catalyzed C-H bond activation using tert-butyl peroxide (TBP) as oxidant under air has been developed. The reaction proceeds smoothly at ambient temperature to furnish the products. A variety of substituted aminobenzoxazoles were synthesized with good to excellent yields.

Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles

The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.

Cobalt(II)-catalyzed isocyanide insertion reaction with amines under ultrasonic conditions: A divergent synthesis of ureas, thioureas and azaheterocycles

Cobalt(II) acetylacetonate-catalyzed isocyanide insertion reactions with amines utilizing tert-butyl hydroperoxide (TBHP) as an oxidant under ultrasound conditions have been developed, which lead to the synthesis of ureas, thioureas, as well as 2-aminoben

Synthesis of 2-aminobenzoxazoles and 3-aminobenzoxazines via palladium-catalyzed aerobic oxidation of o -aminophenols with isocyanides

A Pd-catalyzed aerobic oxidation of o-aminophenols and isocyanides for the synthesis of 2-aminobenzoxazoles and 3-aminobenzoxazines has been achieved in an air atmosphere. The procedure constructs 2-aminobenzoxazoles and 3-aminobenzoxazines with moderate to excellent yields and a broad substrate scope. Apart from experimental simplicity, this methodology has the advantages of mild reaction conditions and easily accessible starting materials. Furthermore, the utility of this method has also been successfully applied to the synthesis of other types of useful nitrogen heterocycles.

Cobalt-catalyzed oxidative isocyanide insertion to amine-based bisnucleophiles: Diverse synthesis of substituted 2-aminobenzimidazoles, 2-aminobenzothiazoles, and 2-aminobenzoxazoles

Cobalt catalysis: Synthesis of substituted 2-aminobenzimidazoles, 2-aminobenzothiazoles, and 2-aminobenzoxazoles was achieved by using cobalt(II) acetate catalyzed isocyanide insertion to o-diaminobenzene, 2-aminobenzenethiol, and 2-aminophenol derivatives in 1,4-dioxane (see scheme). It was found that the reaction proceeded efficiently to give the desired products in up to 95 % isolated yields by C-N and C-S (O, N) formation in a single step. Copyright