1570134-76-7

Upstream product

• 456-22-4 4-Fluorobenzoic acid 
• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 403-43-0 4-fluorobenzoyl chloride 
• 1885-29-6 anthranilic acid nitrile 

Downstream Products

• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 80517-23-3 4 -fluoro-2-((4-methylphenyl)sulfonamido)benzoic acid 
• 1570135-10-2 N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-4-fluoro-2-(4-methylphenylsulfonamido)benzamide 
• 1570135-11-3 5-chloro-N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-2-(4-methylphenylsulfonamido)benzamide 
• 1570135-12-4 3-chloro-N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-2-(4-methylphenylsulfonamido)benzamide 

Relevant academic research and scientific papers

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.

Copper-Mediated Amination of Aryl C-H Bonds with the Direct Use of Aqueous Ammonia via a Disproportionation Pathway

The direct amination of C-H bonds with ammonia is a challenge in synthetic chemistry. Herein, we present a copper-mediated approach that enables a chelation-assisted aromatic C-H bond amination using aqueous ammonia. A key strategy was to use soft low-valent Cu(I) species to avoid the strong coordination of ammonia. Mechanistic investigations suggest that the catalysis is initiated by a facile deprotonation of bound ammonia, and the C-N coupling is achieved by subsequent reductive elimination of the resultant copper-amido intermediate from a Cu(III) intermediate that is readily generated by disproportionation of low-valent copper analogues. This mechanistic postulate was supported by a preliminary kinetic isotope effect study and computations. This new chelation-assisted, copper-mediated C-H bond amination with aqueous ammonia was successfully applied to a broad range of substrates to deliver primary anilines. Moreover, the mild conditions required for this transformation allowed the reaction to operate even under substoichiometric conditions to enable a late-stage application for the preparation of pharmaceutical agents.

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 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.

Amide-Oxazoline Directed ortho-C–H Nitration Mediated by CuII

A CuII-mediated ortho-C–H nitration using amide-oxazoline as the directing group has been developed. The reactions utilize sodium nitrite as the source of the nitro group under O2 atmosphere and proceed smoothly. The desired products can be obtained in yields of 26–94 %.

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 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.

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.