37892-50-5

Upstream product

• 108-88-3 toluene 
• 552-89-6 2-nitro-benzaldehyde 
• 37892-43-6 2-azido-4'-methylbenzophenone 
• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 118-92-3 anthranilic acid 
• 624-31-7 4-tolyl iodide 
• 271-58-9 anthranil 
• 106-38-7 para-bromotoluene 
• 612-23-7 2-nitrobenzyl chloride 
• 859946-84-2 1-methyl-4-(2-nitrobenzyl)benzene 
• 36192-63-9 2-amino-4'-methylbenzophenone 
• 36192-61-7 2-amino-4'-methoxybenzophenone 
• 37892-45-8 2-azido-4'-methoxy-benzophenone 
• 37892-51-6 3-(4-methoxyphenyl)benzo[c]isoxazole 

Downstream Products

• 36192-63-9 2-amino-4'-methylbenzophenone 
• 57165-19-2 3-methyl-10H-acridin-9-one 
• 87895-79-2 2-(2,4-dichlorophenylamino)-4'-methylbenzophenone 
• 23864-43-9 2-methyl-10H-acridin-9-one 
• 71319-20-5 (4-methylphenyl)(2-nitrophenyl)methanone 

Relevant academic research and scientific papers

Reactivity of 2,1-Benzisoxazole in Palladium-Catalyzed Direct Arylation with Aryl Bromides

The Pd-catalyzed direct arylation of 2,1-benzisoxazole with aryl bromides to access 3-arylbenzoisoxazoles proceeds in moderate-to-high yields with 1 mol % Pd(OAc)2 or 2 mol % PdCl(C3H5)(dppb) (dppb=1,4-bis(diphenylphosphino)butane) as the catalysts and KOAc as an inexpensive base. A wide variety of (hetero)aryl bromides have been employed successfully. Moreover, arylations followed by benzisoxazole ring opening allowed the preparation of 2-aminobenzophenones in only two steps. What a couple: The Pd-catalyzed direct arylation of 2,1-benzisoxazole with aryl bromides and 1 mol % of phosphine-free Pd(OAc)2 catalyst in association with KOAc as an inexpensive base allows the preparation of 3-arylbenzoisoxazoles in moderate-to-high yields. Moreover, the 2,1-benzisoxazole C-3-arylations followed by benzisoxazole ring opening gives access to 2-aminobenzophenones in only two steps.

Palladium-Catalyzed Direct C-H Arylation of Isoxazoles at the 5-Position

A palladium-catalyzed direct arylation of isoxazoles with aryl iodides has been achieved. The C-H bond at the 5-position is activated selectively to give coupling products in moderate to good yields. This direct arylation was applied to the synthesis of a spiro-type chiral ligand, which proved to be most effective to the palladium-catalyzed tandem cyclization of a dialkenyl alcohol.

An In-depth Study of the Azidobenzophenone-Anthranil-Acridone Transformation

The title transformation, particularly the conversion of anthranils into acridones, is shown to be critically sensitive to temperature, solvent, substituent, and metal catalysts.Thus the conversion of 3-(p-tolyl)anthranil into an acridone gives a ratio of 2-and 3-methyl derivatives varying from 0.6:1 to 4.7:1 with changing temperature and solvent.In other similar thermolyses, solvents (e.g. 1,2,4-trichlorobenzene) were incorporated into the product and traces of metals and their derivatives had a dramatic effect on the rate and course of the reaction.The most effective catalysts were iron powder and aluminium acetylacetonate. 3-(2,6-Disubstituted phenyl)anthranils gave acridones in which the substituents were either lost or rearranged onto N or C, the last cases involving sequential -sigmatropic shifts. 3-Thienylanthranils gave related thienoquinolones on thermolysis; again the reaction were very sensitive to catalysis.Blocked thienylanthranils also gave rearrangement products, but the non-aromatic intermediates could be isolated.