61820-93-7

Upstream product

• 3230-45-3 (E)-N-benzylidene-2-hydroxyaniline 
• 137838-23-4 cis-N-Benzylidene-o-aminophenol 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 95-55-6 2-amino-phenol 
• 833-50-1 2-phenylbenzo[d]oxazole 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 
• 98-88-4 benzoyl chloride 

Downstream Products

• 833-50-1 2-phenylbenzo[d]oxazole 

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.

Copper-catalyzed synthesis of 2-arylbenzoxazoles from o-aminophenol derivatives with arylmethyl chlorides

A facile and efficient synthesis of 2-arylbenzoxazoles via copper-catalyzed tandem condensation/oxidative reaction of o-aminophenol derivatives with arylmethyl chlorides was developed. Note that this reaction utilized arylmethyl chlorides as a new type of simple and cheap acyl sources and KNO3 as a readily available and low-cost benign oxidant.

Ruthenium-catalyzed synthesis of benzoxazoles using acceptorless dehydrogenative coupling reaction of primary alcohols with 2-aminophenol under heterogeneous conditions

An efficient ruthenium-catalyzed acceptorless dehydrogenative coupling reaction of primary alcohols with 2-aminophenol for one-pot synthesis of benzoxazoles is introduced. The phosphine-functionalized magnetic nanoparticles (PFMNPs; Fe3O4@SiO2@PPh2) as a magnetic recyclable phosphorus ligand in the presence of Ru2Cl 4(CO)6 was found to be an efficient heterogeneous catalytic system for promotion of the designed protocol. The reaction was carried out efficiently with a variety of substrates to give the corresponding products in moderate to good yields.

Parallel synthesis of benzoxazoles via microwave-assisted dielectric heating

A facile route to benzoxazoles has been developed using microwave-assisted dielectric heating. The ease of synthesis and workup allowed the parallel synthesis of a 48-membered library of benzoxazoles quickly and efficiently.

SYNTHETIC STUDIES USING AROMATIC AMINO COMPOUNDS AND ACTIVATED NITRILES

Reaction of malononitrile, arylidenemalononitrile, chloroacetonitrile or ethyl cyanoacetate with o-aminobenzenethiol, o-aminophenol, 2-aminobenzothiazole, anthranilamide, o-phenylenediamine, p-nitro-o-phenylenediamine, 2-naphthylamine, 2-amino-3-hydroxypyridine or 2,3-diaminopyridine afforded a new series of nitrogen-containing mono- or poly-heterocyclic derivatives via initial addition to either the cyano or the styryl function followed by cyclization.The structure of the obtained products was elucidated by microanalyses, IR and NMR data.

Photochemical and Thermal Reactions of Aromatic Schiff Bases

The photochemical and thermal reactions of aromatic Schiff bases (SB) prepared from o-aminophenol and aldehydes and from o-aminophenol and ketones are compared.All SB's are converted by light into the corresponding benzoxazolines.For the SB's derived from aldehydes, benzoxazoline formation is a prerequisite to convert them by a second photon into benzoxazoles.In some cases oxygen is not required for this second reaction step.SB's derived from ketones are converted into benzoxazoles by the absorption of just one photon, but only in the presence of oxygen and only if the aliphatic residue R1 of the N=C(R1R2) bridge contains at least two carbon atoms.A radical mechanism is proposed for this reaction.Benzoxazine formation is observed in some cases as a thermal side reaction.The photochemical reactions of the latter were also investigated.