5998-50-5

Upstream product

• 95-55-6 2-amino-phenol 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 273-53-0 benzoxazole 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 389840-61-3 N-4-tert-butylbenzylidene-2-hydroxyaniline 
• 939-97-9 4-tert-Butylbenzaldehyde 
• 59970-38-6 4-tert-butylphenyl mesylate 
• 905966-37-2 2-(4-(tert-butyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 1710-98-1 p-tert-butyl benzoyl chloride 
• 65604-75-3 4-(tert-butyl)benzenesulfonyl hydrazide 
• 39895-55-1 4-(1,1-dimethylethyl)-benzenemethanamine 
• 772-38-3 4-tert-Butylphenylacetylene 
• 85609-03-6 phenyl p-(tert-butyl)phenyl sulfide 
• 56108-12-4 4-tert-butylbenzamide 

Relevant academic research and scientific papers

Delivering 2-Aryl Benzoxazoles through Metal-Free and Redox-Neutral De-CF3Process

An unexpected cleavage of the Csp3-CF3 bond of CF3-hydrobenzoxazoles has been disclosed, affording a range of 2-aryl benzoxazoles under metal-free and redox-neutral conditions. This transformation has demonstrated broad substrate scope and good compatibility of functional groups. 2-Aryl benzothiazole and 2-aryl benzoimidazole could be smoothly assembled in the same manner. On the basis of preliminary mechanistic studies, base initiated and aromatization driven β-carbon elimination was considered to be the key step for the formation of 2. This reaction offers an alternative, facile, and sustainable route to access important 2-aryl benzoxazole motifs.

Nickel catalyzed sustainable synthesis of benzazoles and purines: Via acceptorless dehydrogenative coupling and borrowing hydrogen approach

Herein we report nickel-catalyzed sustainable synthesis of a few chosen five-membered fused nitrogen heterocycles such as benzimidazole, purine, benzothiazole, and benzoxazole via acceptorless dehydrogenative functionalization of alcohols. Using a bench stable, easy to prepare, and inexpensive Ni(ii)-catalyst, [Ni(MeTAA)] (1a), featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)), a wide variety of polysubstituted benzimidazole, purine, benzothiazole, and benzoxazole derivatives were prepared via dehydrogenative coupling of alcohols with 1,2-diaminobenzene, 4,5-diaminopyrimidine, 2-aminothiphenol, and 2-aminophenol, respectively. A wide array of benzimidazoles were also prepared via a borrowing hydrogen approach involving alcohols as hydrogen donors and 2-nitroanilines as hydrogen acceptors. A few control experiments were performed to understand the reaction mechanism.

2-ARYLBENZIMIDAZOLES AS PPARGC1A ACTIVATORS FOR TREATING NEURODEGENERATIVE DISEASES

A genus of compounds encompassed by formula (III) and their use is disclosed: Formula (III). The compounds activate Ppargc1a and, as a consequence, are useful for treating a variety of neurodegenerative diseases such as amyotrophic lateral sclerosis (ALS), Alzheimer's disease, Parkinson's disease, Huntington's disease, frontotemporal degeneration, dementia with Lewy bodies, motor neuron diseases, and a demyelinating disease.

Straightforward synthesis of benzoxazoles and benzothiazoles via photocatalytic radical cyclization of 2-substituted anilines with aldehydes

Eosin Y-catalyzed one-pot coupling and cyclization of o-substituted anilines with aldehydes to form benzoxazoles and benzothiazoles under mild condition has been developed. The reaction scope was broadly tolerant of various 2-substituted anilines and aldehydes. The desired products were obtained in high yields with the use of eosin Y as a photocatalyst under a substantial refinement of reaction conditions in comparison with previous literature. Based on the experimental results observed, a plausible mechanism involving a radical process has been proposed.

Phosphine-phosphonium ylides as ligands in palladium-catalysed C2-H arylation of benzoxazoles

As balanced electron-rich P,C-chelating ligands, phosphine-phosphonium-ylides are considered for their ability to in situ promote palladium-catalysed direct C(sp2)–H arylation. Using methyl phosphonium salts of 2,2'-bis(diphenylphosphino)-1,1'-binaphtyl (“methyl-BINAPIUM”) as ylide precursors under optimized reaction conditions, arylation of benzoxazole was found to proceed in moderate to high yield to give functional 2-aryl benzoxazoles. A strong anion effect of the non-salt free ylide was evidenced (TfO? > I? > PF6? ≈ salt-free). This first example of phosphonium ylides as ligands in catalytic C–H activation extends the prospect of their general implementation in homogeneous transition metal catalysis.

Visible Light-Induced Copper-Catalyzed C—H Arylation of Benzoxazoles?

A general method for visible light-induced copper-catalyzed arylation of sp2 C—H bonds of azoles has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide as base. A variety of azoles including benzooxazole and benzothiazole can be arylated. Furthermore, electron-poor heterocycles such as thiophene possessing one electron-withdrawing group can also be arylated.

Sulfur/DABCO Promoted Reductive Coupling/Annulation Cascade Reaction between o -Hydroxy/Amino Nitrobenzenes and Benzaldehydes

Sulfur/DABCO was found to be an efficient reagent in promoting- the reductive coupling/annulation of o -nitrophenols or o -nitroanilines with benzaldehydes. This method represents a simple, straightforward, and green approach to the construction of benz-oxazoles and benzimidazoles.

Pd/Cu bimetallic co-catalyzed direct 2-arylation of benzoxazole with aryl chloride

An efficient Palladium/Copper bimetallic co-catalyzed direct 2-arylation of benzoxazoles with aryl chlorides is presented. The Pd(OAc)2/CuI/NiXantphos-based catalyst enables the installation of various aryl and heteroaryl groups in good to excellent yields (75–99%). Preliminary mechanism investigation indicates that Pd/Nixantphos complex activates C-Cl bond of aryl chlorides via oxidative addition, and Cu/Nixantphos complex chelates with nitrogen atom to lower the pKa of the 2-H in benzoxazoles.

Phosphonium acidic ionic liquid: An efficient and recyclable homogeneous catalyst for the synthesis of 2-Arylbenzoxazoles, 2-Arylbenzimidazoles, and 2-Arylbenzothiazoles

A highly efficient and green strategy for the synthesis of 2-Arylbenzoxazoles, 2-Arylbenzimidazoles, and 2-Arylbenzothiazoles catalyzed by phosphonium acidic ionic liquid has been developed via the condensation of o-Aminophenol, o-phenylenediamines, and o-Aminothiophenol, respectively, with aldehydes. The reaction has a good yield, the broad substrate scope, and mild condition. Triphenyl(butyl-3-sulphonyl)phosphonium toluenesulfonate catalyst was easily obtained from cheap and available starting materials through a one-pot synthesis. Its structure was identified by 1H NMR, 13C NMR, 31P NMR, and FT-IR techniques. Other properties including thermal stability and acidity were determined by TGA and Hammett acidity function method. Interestingly, the catalyst can maintain its constantly outstanding performance till the fourth recovery.

Deep eutectic solvent-catalyzed arylation of benzoxazoles with aromatic aldehydes

A novel and efficient methodology for the arylation of benzoxazoles with aromatic aldehydes catalyzed by deep eutectic solvent has been developed. The reaction smoothly proceeded with a wide range of substrates to give the desired products in high yields within short reaction time. Deep eutectic solvents are easily recovered and reused without significant loss of catalytic activity.