106590-21-0

Upstream product

• 13337-77-4 N-(2-oxo-2-phenylethyl)nicotinamide 
• 10400-19-8 3-pyridinecarbonyl chloride 
• 58644-55-6 (3-Pyridylmethyl)isonitrile 
• 98-88-4 benzoyl chloride 
• 500-22-1 3-pyridinecarboxaldehyde 
• 5468-37-1 2-aminoacetophenone hydrochloride 
• 59-67-6 nicotinic acid 
• 1006-68-4 5-phenyloxazole 
• 3468-53-9 phenyl nicotinate 
• 24303-08-0 N-(2-phenylethyl)pyridine-3-carboxamide 
• 3731-52-0 3-Aminomethylpyridine 
• 70-11-1 α-bromoacetophenone 
• 100-54-9 pyridine-3-carbonitrile 
• 122-78-1 phenylacetaldehyde 

Relevant academic research and scientific papers

Synthesis of Substituted Oxazoles by Visible-Light Photocatalysis

A simple and practical method for the synthesis of substituted oxazoles has been developed using readily available α-bromoketones and benzylamines by visible-light photocatalysis at room temperature. The process, which requires 1 mol % of [Ru(bpy)3]Cl2 photocatalyst with K3PO4 and CCl3Br, is effective for accessing a variety of valuable oxazole compounds. The synthetic utility of our protocol was also demonstrated by preparing a natural product, texaline.

Method of coupling, and the coupling method using the aromatic group-substituted heterocyclic compound

Provided is an easy method (coupling method) capable of easily synthesizing a compound group in which aromatic molecules and aromatic molecules are coupled, a compound group in which aromatic molecules and alkene molecules are coupled, and the like without producing halogen waste and without the need to use scarce and expensive palladium. A compound (A) shown by general formula (A): Ar-H and a compound (B1) shown by general formula (B1): RaOCO-Ar', a compound (B2) shown by general formula (B2): RbCH=C(Ar")2, or a compound (B3) shown by general formula (B3): RcOCOCH=C(Ar")2 are reacted in the presence of a nickel compound.

Nickel-Catalyzed Coupling of Azoles with Aromatic Nitriles

This manuscript describes the Ni-catalyzed coupling of azoles with aromatic nitriles. The use of BPh3 promotes these arylations with electronically diverse azoles and benzonitriles. While the nickel catalyst is necessary for the arylations of phenyl oxazoles, arylation of benzoxazoles with some nitriles affords the arylated products even in the absence of the Ni catalyst albeit in lower yield than the catalyzed process. The Ni-catalyzed process exhibits higher rates and a broader scope than the uncatalyzed transformation.

Iodine catalysed intramolecular C(sp3)-H functionalization: synthesis of 2,5-disubstituted oxazoles from N-arylethylamides

Iodine catalyzed synthesis of 2,5-disubstituted oxazoles from N-arylethylamides through intramolecular C(sp3)-H functionalization under metal-free conditions is described. The method is tolerable to a wide range of substrates having a variety of functional groups with moderate to good yields of the products.

Iodine(III)-promoted synthesis of oxazoles through oxidative cyclization of N -styrylbenzamides

The hypervalent iodine reagent PhI(OTf)2, generated in situ, has been successfully utilized in an intramolecular oxidative cyclization of N-styrylbenzamides. In remarkably short reaction times, the desired 2,5-disubstituted oxazoles were isolated in high yields in this metal-free oxidative C-O bond-forming reaction. Georg Thieme Verlag Stuttgart, New York.

Metal-free dual sp3 C-H functionalization: I2- promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles

An I2-promoted sp3 C-H functionalization has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available methyl ketones and benzylamines without any metal and peroxide catalyst. This domino oxidative cyclization process involves the cleavage of C-H bond and the formation of C-N, C-O bonds.

Decarbonylative C-H coupling of azoles and aryl esters: Unprecedented nickel catalysis and application to the synthesis of muscoride A

A nickel-catalyzed decarbonylative C-H biaryl coupling of azoles and aryl esters is described. The newly developed catalytic system does not require the use of expensive metal catalysts or silver- or copper-based stoichiometric oxidants. We have successfully applied this new C-H arylation reaction to a convergent formal synthesis of muscoride A.

Simple and efficient preparation of 2,5-disubstituted oxazoles via a metal-free-catalyzed cascade cyclization

A practical and simple synthesis of 2,5-disubstituted oxazoles was developed via an iodine-catalyzed tandem oxidative cyclization. A wide range of common commercial aromatic aldehydes can be used as reaction substrates, which displayed excellent functional group compatibility in this reaction.

Unconventional oxazole formation from isocyanides

The coupling of an acyl chloride with an isocyanide affords 2,5-disubstituted oxazoles under mild basic conditions instead of 4,5-disubstituted derivatives when using Schoellkopf conditions (butyllithium); this reaction constitutes a remarkable example of a base-induced chemoselective process in isocyanide chemistry.

C-H bond activation: A versatile protocol for the direct arylation and alkenylation of oxazoles

The versatile palladium, complex Pd(PPh3)4 catalyses both direct arylation and alkenylation of oxazoles efficiently. The method is regioselective and stereospecific with respect to bromoalkenes and tolerates a wide range of functional groups.