1570134-82-5

Upstream product

• 586-76-5 4-Bromobenzoic acid 
• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 586-75-4 4-chlorobenzoyl chloride 
• 1885-29-6 anthranilic acid nitrile 
• 201230-82-2 carbon monoxide 
• 589-87-7 1,4-bromoiodobenzene 

Downstream Products

• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 31100-22-8 4-Brom-2-tosylamino-benzoesaeure 
• 1570135-14-6 4-bromo-N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-2-(4-methylphenylsulfonamido)benzamide 

Relevant academic research and scientific papers

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.

Rhodium(III)-catalyzed chemodivergent annulations between phenyloxazoles and diazos via C–H activation

Acid-controlled, chemodivergent and redox-neutral annulations for the synthesis of isocoumarins and isoquinolinones have been realized via Rh(III)-catalyzed C[sbnd]H activation. Diazo compounds act as a carbene precursor, and coupling occurs in one-pot process, where adipic acid and trimethylacetic acid promote chemodivergent cyclizations.

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.

Synthesis of quinazoin-4-ones through an acid ion exchange resin mediated cascade reaction

An interesting cascade reaction of N-(2-(4,5-dihydrooxazol-2-yl)phenyl)benzamide in the presence of an acid ion exchange resin is described. In this reaction, a range of substrates bearing various substituent groups are well compatible. This work provides a green and atom-economical alternative approach for the synthesis of quinazolin-4-ones in good yields.

Synthesis of quinazolin-4(1 H)-ones via amination and annulation of amidines and benzamides

Quinazolinones have broad applications in the biological, pharmaceutical and material fields. Studies on the synthesis of these compounds are therefore widely conducted. Herein, a novel and highly efficient copper-mediated tandem C(sp2)-H amination and annulation of benzamides and amidines for the synthesis of quinazolin-4(1H)-ones is proposed. This synthetic route can be useful for the construction of quinazolin-4(1H)-one frameworks.

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.

Synthesis method of 2-aryl oxazoline amide compound

The invention discloses a synthesis method of a 2-aryl oxazoline amide compound. The method comprises the following steps that 2-oxazolinyl aniline, an aryl iodide compound, alkali, a metal palladiumcompound and an organic solvent are sequentially added into a reaction container; stirring is performed at room temperature; CO gas is introduced for 10 to 15 min; then, the reaction system is sealed;after the temperature is raised to 80 to 100 DEG C, reaction is performed for 10 to 15 h; after the reaction is finished, rotary evaporation concentration and chromatographic separation are performedto obtain the 2-aryl oxazoline amide compound. The 2-aryl oxazoline amide compound is a compound shown as a general formula I in the description; in the general formula, R is hydrogen, alkyl, -OMe, -CF3 or halogen. The synthesis steps are simple and convenient; CO is used as a starting material, is cheap and can be easily obtained; higher yield and substrate universality are realized; under mostconditions, the yield is greater than 90 percent. The 2-aryl oxazoline amide compound provided by the method has wide application to the field of organic synthesis, particularly bidentate guide base strategy assistant inert C-H bond activation.

Nickel-Catalyzed Regioselective C–H Bond Mono- and Bis-Nitration of Aryloxazolines with tert-Butyl Nitrite as Nitro Source

An efficient and regioselective nickel-catalyzed remote C–H nitration of 2-aryloxazoline amides using the non-corrosive tert-butyl nitrite (TBN) as nitro source has been developed. The protocol makes use of inexpensive nickel salts as catalysts and delivers the corresponding products in excellent yields. Notably, bis-nitration products were obtained by simply increasing the amount of tert-butyl nitrite. This reaction proceeds in air and features excellent functional group compatibility, broad substrate scope and is suitable for gram-scale synthesis. (Figure presented.).

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 ortho C-H alkynylation of (hetero)arenes with terminal alkynes

Cu(II)-promoted ortho alkynylation of arenes and heteroarenes with terminal alkynes has been developed to prepare aryl alkynes. A variety of arenes and terminal alkynes bearing different substituents are compatible with this reaction, thus providing an alternative disconnection to Sonogashira coupling.