73713-90-3

Usage

InChI:InChI=1/C20H15NO/c1-3-9-15(10-4-1)19(16-11-5-2-6-12-16)20-21-17-13-7-8-14-18(17)22-20/h1-14,19H

Upstream product

• 76929-77-6 α-(2-benzoxazolyl)diphenylmethanol 
• 591-50-4 iodobenzene 
• 2008-07-3 2-benzyl-1,3-benzoxazole 
• 117-34-0 2,2-diphenylacetic acid 
• 95-55-6 2-amino-phenol 
• 273-53-0 benzoxazole 
• 5433-76-1 diphenylmethyl phenyl sulfone 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 667458-78-8 benzyl 3,5-bis(trifluoromethyl)phenyl sulfone 
• 91-01-0 1,1-Diphenylmethanol 
• 95-21-6 2-methyl-1,3-benzoxazole 
• 119-61-9 benzophenone 
• 4545-20-4 benzophenone tosylhydrazone 

Relevant academic research and scientific papers

Catalytic Direct α-Amination of Arylacetic Acid Synthons with Anilines

A unique α-amination approach using various anilines has been developed for arylacetic acids via adaptation as benzazoles. The reaction proceeds through a single electron transfer mechanism utilizing an iron-based catalyst system to access α-(N-arylamino)acetic acid equivalents. Modification of approved drugs, facile cleavage of the benzazole auxiliary, and tolerance of amide linkage forming conditions constitute the potential applicability of this strategy.

Pd-Catalyzed Desulfonative Cross-Coupling of Benzylic Sulfone Derivatives with 1,3-Oxazoles

The Pd-catalyzed desulfonative cross-coupling reaction of benzylic sulfone derivatives with 1,3-oxazoles via a deprotonative pathway has been developed. Broad substrate scope for both sulfone and 1,3-oxazole partners is observed, affording a variety of 1,3-oxazole-containing triarylmethanes. Sulfone partners that are primary benzylic, secondary benzylic, and benzhydryl are all effective. Using this method, the straightforward synthesis of multiply arylated structures has been demonstrated.

Trichloroisocyanuric Acid/Triphenylphosphine-Mediated Synthesis of Benzimidazoles, Benzoxazoles, and Benzothiazoles

A new and efficient method for preparation of benzimidazoles, benzoxazoles, and benzothiazoles from reactions of different carboxylic acids with o-phenylenediamine, o-aminophenol, and o-aminothiophenol in the presence of triphenylphosphine/trichloroisocyanuric acid system is presented. The desired products have been characterised on the basis of spectral (infrared, NMR, mass spectrometry) data, and the mechanism of their formation is proposed. The remarkable advantages are the inexpensive and readily available reagent, simple procedure, mild conditions, and good-to-excellent yields.

Synthesis of triarylmethanes by palladium-catalyzed c-h/c-o coupling of oxazoles and diarylmethanol derivatives

A PdCl2(MeCN)2/PPhCy2 catalyst couples oxazoles with diarylmethyl carbonates or pivalates to form the corresponding triarylmethanes in good yields. The catalysis involves successive secondary benzylic sp3 C-O and heteroaromatic sp2 C-H cleavages and provides an effective access to heteroarene-containing triarylmethanes from nonhalogenated and nonmetalated starting materials, which is complementary to precedented cross-coupling technologies with organic halides and organometallic reagents.

Pd(0)-catalyzed diarylation of sp3 C-H bond in (2-azaaryl)methanes

A highly efficient and selective palladium-catalyzed diarylation of (2-azaaryl)methanes at the methyl group is described. Aryl chlorides proved reactive enough. A palladium η3-azaallyl intermediate has been identified on the basis of DFT studies.

Copper-catalyzed direct benzylation or allylation of 1,3-azoles with N -tosylhydrazones

Cu-Catalyzed cross-coupling of N-tosylhydrazones with 1,3-azoles leads to the direct C-H benzylation or allylation. Cu carbene migratory insertion is proposed to play the key role in this transformation.

Palladium-catalyzed direct arylation of aryl(azaaryl)methanes with aryl halides providing triarylmethanes

Direct arylation of aryl(azaaryl)methanes with aryl halidas takes place at the benzylic position in the presence of a hydroxide base under palladium catalysis to yield triarylmethanes

Facile synthesis of 2-substituted benzoxazoles via ketenes

The generation of diphenyl-, phenyl-, phenoxy-, and chloroketenes by treatment of the corresponding acid chlorides with triethylamine in the presence of 2-aminophenol resulted in good yields of 2-substituted benzoxazoles.