37038-65-6

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 615-36-1 2-bromoaniline 
• 619-56-7 4-chlorobenzamide 

Downstream Products

• 1141-35-1 2-(4-chlorophenyl)benzoxazole 
• 18600-52-7 2-(4-chlorophenyl)-4H-benzo[d][1,3]oxazin-4-one 
• 103517-58-4 2'-amino-4-chlorobenzanilide 
• 6833-15-4 4-chlorobenzanilide 
• 6265-91-4 2-(4-chlorophenyl)benzothiazole 
• 37038-50-9 2'-Brom-4-chlor-N-nitrosobenzanilid 
• 93-98-1 N-phenyl benzoyl amide 

Relevant academic research and scientific papers

Photocatalyst- And Transition-Metal-Free Visible-Light-Promoted Intramolecular C(sp2)-S Formation

A photocatalyst- and transition-metal-free visible-light-induced cyclization of ortho-halothiobenzanilides has been developed. Upon irradiation with visible light, substrates undergo dehalogenative cyclization to 2-aryl benzothiazoles with high efficiency and selectivity. This photocyclization exhibits a high tolerance to various functional groups, is applicable for the synthesis of 2-alkyl benzothiazoles, and is easy to set up for gram-scale reaction.

Iridium-catalyzed intramolecular C–N and C–O/S cross-coupling reactions: Preparation of benzoazole derivatives

The irdium-catalyzed intramolecular arylcarbon-hetero cross-coupling reactions with o-haloarylamides or o-haloarylamidine have been effectively achieved using KOAc and just 1 mol% catalyst. The [Ir(cod)Cl]2 was proved to be more potential for smoothly assembling functional structures benzimidazoles, benzoxazoles and benzothiazoles, which was superior to Cu- and Pd-catalyzed systems. Simultaneously, a concise and efficient synthesis of tafamidis was developed in 5-g scale.

A comparative study of the catalytic activity of Co- and CoFe2O4-NPs in C-N and C-O bond formation: synthesis of benzimidazoles and benzoxazoles from o-haloanilides

Nanoparticles of cobalt ferrite (CoFe2O4-NPs) and pure cobalt (Co-NPs) were synthesized, and after characterization, their catalytic activities for dehalogenative intramolecular C-O and C-N bond formation reactions were investigated and compared. These inexpensive and efficient catalysts enabled creation of new methods for the synthesis of benzimidazoles and benzoxazoles in green media, with ligand-free and mild reaction conditions. All the reactions resulted in moderate to excellent yields under the optimized reaction conditions; however, the reactions using Co-NPs as the catalyst were completed in relatively shorter reaction times. Furthermore, analysis showed that the reusability of the two catalytic systems is approximately comparable.

Palladium-catalyzed carbonylative synthesis of benzoxazinones from N -(o -bromoaryl)amides using paraformaldehyde as the carbonyl source

Carbonylation reactions have been widely used in organic synthesis. However, the manipulation of toxic and pressurized carbon monoxide limited their applications in organic laboratories. The search for alternative carbonyl sources as an important method for carbonylative organic synthesis is spreading. Herein, a series of substituted benzoxazinones were synthesized from N-(o-bromoaryl)amides by palladium-catalyzed carbonylation with paraformaldehyde as the carbonyl source, which is inexpensive, stable, and easy to use. Notably, this is the first example of using paraformaldehyde as the CO source in palladium-catalyzed carbonylative synthesis of heterocycles.

Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides

A general method for the formation of benzoxazoles via a copper-catalyzed cyclization of ortho-haloanilides is reported. This approach complements the more commonly used strategies for benzoxazole formation which require 2-aminophenols as substrates. The reaction involves an intramolecular C-O cross-coupling of the ortho-haloanilides and is believed to proceed via an oxidative insertion/reductive elimination pathway through a Cu(I)/Cu(III) manifold. The reaction is also applicable to the formation of benzothiazoles. A variety of ligands including 1,10-phenanthroline and N,N′- dimethylethylenediamine were shown to provide ligand acceleration/stabilization in the reaction. Optimal conditions for cyclization used a catalyst combination of CuI and 1,10-phenanthroline (10 mol %). The method was amenable to a parallel-synthesis approach, as demonstrated by the synthesis of a library of benzoxazoles and benzothiazoles substituted at various positions in the ring. Most examples utilized the cyclization of ortho-bromoanilides, but orthoiodoanilides and ortho-chloroanilides also undergo a reaction under these conditions. The rate of reaction of the ortho-haloanilides follows the order I > Br > Cl, consistent with oxidative addition being the rate-determining step.