1629-77-2

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 618-46-2 m-Chlorobenzoyl chloride 
• 1128-76-3 3-chloro-benzoic acid ethyl ester 
• 39582-59-7 benzothiazol-2-yl-lithium 
• 1141-88-4 2-Aminophenyl disulfide 
• 99-02-5 3'-Chloroacetophenone 
• 67829-05-4 1-(3-chlorophenyl)-2-hydroxyethanone 
• 137-07-5 2-amino-benzenethiol 
• 62-53-3 aniline 
• 108-41-8 1-chloro-3-methylbenzene 

Relevant academic research and scientific papers

Visible-light-promoted photocatalyst-free alkylation and acylation of benzothiazoles

Herein we report a protocol for the visible-light-mediated alkylation/acylation reaction of benzothiazoles. Alkyl/acyl substituted Hantzsch esters are easily prepared and rationally used as radical precursors. In the presence of BF3·Et2O and Na2S2O8, various benzothiazole derivatives were readily obtained in good yields. Our user-friendly protocol can proceed by simple irradiation with blue LEDs (λ = 465 nm) and without the assistance of external photocatalysts. The reaction is also characterized by mild conditions and scalability, thus offering an alternative and efficient tool for the synthesis of 2-functionalized benzothiazoles.

Oxidant/Solvent-Controlled I2-Catalyzed Domino Annulation for Selective Synthesis of 2-Aroylbenzothiazoles and 2-Arylbenzothiazoles under Metal-Free Conditions

A simple and practical domino protocol for the selective synthesis of 2-aroylbenzothiazoles and 2-aryl benzothiazoles catalyzed by I2 is developed under metal-free conditions. The reaction outcomes are exclusively controlled by the reaction oxidant/medium. With DMSO employed as both the solvent and the oxidant, an oxidation of aromatic methyl ketones takes precedence over the condensation with 2-aminobenzenethiols. On the other hand, when the reaction was carried out in PhNO2 or in 1,4-dioxane containing PhNO2, the condensation of aromatic methyl ketones with 2-aminobenzenethiols has priority to form imines which is followed by an oxidation of the methyl group from ketones to afford 2-arylbenzothiazoles as a sole product. The PhNO2/I2 co-catalytic system is proposed first time.

C2 substituted 2H-benzothiazole aryl acylated derivative, and synthesis method and application thereof

The invention discloses a C2 substituted 2H-benzothiazole aryl acylated derivative, and a synthesis method and application thereof. The preparation method of the derivative comprises the following steps: mixing substituted 2H-benzothiazole and substituted methyl benzene, adding into a solvent, in the presence of an oxidizing agent Selectfluor and an additive trifluoroacetic acid, carrying out a heating and stirring reaction in the air atmosphere, performing TLC monitoring is conducted till the reaction is finished, and separating and purifying the obtained reaction liquid to obtain the target product C2 substituted 2H-benzothiazole aryl acylated derivative. The substituted methyl benzene used in the invention is low in price, easy to obtain and good in chemical stability, the method has the advantages of being high in atom economy, simple in catalytic system, free of transition metal catalysts, good in product yield, wide in substrate range and the like, and the prepared compound structure can be further optimized as an anti-tumor drug lead.

C2-arylacylation of 2H-benzothiazoles with methyl arenes via Selectfluor oxidation

An efficient Selectfluor-oxidative protocol was developed for the direct C2-arylacylation of 2H-benzothiazoles via the radical reaction of 2H-benzothiazoles with methyl arenes. Selectfluor can effectively promote the oxidative cross-coupling without an ex

Photoinduced remote heteroaryl migration accompanied by cyanoalkylacylation in continuous flow

A photoinduced 1,4-heteroaryl migration from a carbon center to a nitrogen center accompanied by a cyanoalkylacylation of heterocyclic-substituted azidyl homoallylic alcohols and cycloketone oxime esters has been described. This simple and powerful protoc

Iodine- And TBHP-Promoted Acylation of Benzothiazoles under Metal-Free Conditions

A simple protocol for the synthesis of 2-acylbenzothiazoles using aryl ketones and benzothiazoles in the presence of I 2and TBHP is described. Acylation of the benzothiazoles is achieved through a sequence involving oxidation of the aryl ketone to an aryl glyoxal, ring-opening of the benzothiazole followed by condensation of the amino group with the aryl glyoxal, cyclization and oxidation. The method avoids the use of metals and toxic solvents. In addition, this protocol has the advantage of broad scope and provides good to excellent product yields.

Preparation method of C2 substituted 2H-benzothiazole acylation derivative

The invention discloses a preparation method of a C2 substituted 2Hbenzothiazole acylation derivative. The preparation method comprises the following steps: mixing 2Hbenzothiazole with substituted methyl benzene, adding an oxidizing agent K2S2O8, reacting in an air atmosphere, carrying out TLC (Thin Layer Chromatography) monitoring until the reaction is finished, and separating and purifying the reaction solution to obtain the C2 substituted 2Hbenzothiazole acylation derivative. By the adoption of the technology, K2S2O8 serves as an oxidizing agent, the C2-substituted 2Hbenzothiazole acylationderivative is synthesized through a heating reaction in the air atmosphere, and the method is simple in catalytic system, good in product yield, wide in substrate range and suitable for application and popularization.

New synthesis of 2-aroylbenzothiazolesviametal-free domino transformations of anilines, acetophenones, and elemental sulfur

A new synthesis of 2-aroylbenzothiazolesviaiodine-promoted domino transformations of anilines, acetophenones, and elemental sulfur was demonstrated. The highlights of this tandem synthesis are (1) easily available anilines and acetophenones as feedstock;

Method for simply and conveniently synthesizing heterocyclic aryl ketone compound

The invention discloses a method for simply and conveniently synthesizing a heterocyclic aryl ketone compound, and belongs to the technical field of the organic chemistry. The method comprises the following steps: using a benzyl heterocyclic compound as a reaction raw material, in a polar solvent, heating and reacting in an oxygen atmosphere, to obtain a multi-substituted ketone compound. The method is capable of using molecular oxygen as an oxidizing agent, green and environmental, and capable of preparing ketone by directly promoting selective oxidation and functionalization of a Csp3-H bond, and broadening a synthetic method for the ketone compound.

Ball-milling synthesized hydrotalcite supported Cu-Mn mixed oxide under solvent-free conditions: An active catalyst for aerobic oxidative synthesis of 2-acylbenzothiazoles and quinoxalines

A rapid solvent-free ball-milling method was developed to prepare a hydrophobic hydrotalcite supported Cu-Mn mixed oxide catalyst (Cu-Mn/HT). The mechanochemically prepared catalyst exhibited high catalytic activity and recyclability towards the aerobic synthesis of 2-acylbenzothiazoles and quinoxalines in green medium ethanol compared with the ones synthesized via grinding and wet-impregnation. Moreover, control experiments showed that the catalyst was successfully used in green oxidative esterification and coupling as well. Cu-Mn/HT was characterized by BET, ICP, XRD, XPS, SEM and TEM, which indicated that more surface oxygen vacancies and formed CuMn2O4 species on HT might contribute to the catalytic activity.