1570134-65-4

Upstream product

• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 766-85-8 3-methoxy-1-iodobenzene 
• 201230-82-2 carbon monoxide 
• 1711-05-3 m-anisoyl chloride 
• 1885-29-6 anthranilic acid nitrile 
• 586-38-9 3-Methoxybenzoic acid 

Downstream Products

• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 1570135-00-0 N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-5-methoxy-2-(4-methylphenylsulfonamido)benzamide 

Relevant academic research and scientific papers

Base-promoted Lewis acid catalyzed synthesis of quinazoline derivatives

A one-pot protocol has been developed for the synthesis of quinazolinones from amide-oxazolines with TsCl via a cyclic 1,3-azaoxonium intermediate and 6π electron cyclization in the presence of a Lewis acid and base. The process is operationally simple and has a broad substrate scope. This method provides a unique strategy for the construction of quinazolinones.

Palladium-catalyzed aminocarbonylation of aryl iodides with amines: efficient access to bidentate amide directing groups

A new route to bidentate amide directing groups has been developed via the palladium(II)-catalyzed aminocarbonylation. Under atmospheric carbon monoxide pressure, using commercially available aryl iodides and aromatic amine derivatives as substrates, the three-component reaction proceeded smoothly to give the desired products in moderate-to-excellent yields with good functional-group compatibility.

Cu-Catalyzed C-H Alkenylation of Benzoic Acid and Acrylic Acid Derivatives with Vinyl Boronates

An efficient Cu-catalyzed C-H alkenylation with acyclic and cyclic vinyl boronates was realized for the first time under mild conditions. The scope of the vinyl borons and the compatibility with functional groups including heterocycles are superior than Pd-catalyzed C-H coupling with vinyl borons, providing a reliable access to multisubstituted alkenes and dienes. Subsequent hydrogenation of the product from the internal vinyl borons will lead to installation of secondary alkyls.

Cu-Mediated C-H Thioetherification of Arenes at Room Temperature

Cu-mediated C-H thioetherification of arenes with ethylene sulfide has been developed using a readily removable directing group. The reaction proceeded at room temperature, and a variety of sensitive functional groups including chloro, bromo, and vinyl were well tolerated. The thiolated products could be converted to the seven-membered benzoxathiepinones derivatives by a sequence of hydrolysis-lactonization reactions.

Cu(II)-catalyzed coupling of aromatic C-H bonds with malonates

A new Cu(II)-catalyzed oxidative coupling of arenes with malonates has been developed using an amide-oxazoline directing group. The reaction proceeds via C(sp2)-H activation and malonate coupling, followed by intramolecular oxidative N-C bond formation. A variety of arenes bearing different substituents are shown to be compatible with this reaction.

Cu(II)-mediated C-H amidation and amination of arenes: Exceptional compatibility with heterocycles

A Cu(OAc)2-mediated C-H amidation and amination of arenes and heteroarenes has been developed using a readily removable directing group. A wide range of sulfonamides, amides, and anilines function as amine donors in this reaction. Heterocycles present in both reactants are tolerated, making this a broadly applicable method for the synthesis of a family of inhibitors including 2-benzamidobenzoic acids and N-phenylaminobenzoates.