1591-92-0

Upstream product

• 118-48-9 isatoic anhydride 
• 5720-07-0 4-methoxyphenylboronic acid 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 150-76-5 4-methoxy-phenol 

Downstream Products

• 153905-34-1 4-methoxyphenyl N-chloroacetylanthranylate 
• 132525-34-9 C₂₀H₁₇N₃O₃ 
• 153905-29-4 2-chloroacetylamino-2'-hydroxy-5'-methoxybenzophenone 

Relevant academic research and scientific papers

Ruthenium(ii)-catalyzed decarbonylative and decarboxylative coupling of isatoic anhydrides with salicylaldehydes: access to aryl 2-aminobenzoates

A ruthenium(ii)-catalyzed coupling reaction of isatoic anhydrides and salicylaldehydes has been developed for the synthesis of 2-aminobenzoates. This reaction proceeds through metal-catalyzed decarbonylation and decarboxylation to afford good yields of aryl 2-aminobenzoates.

Palladium-catalyzed decarboxylative coupling of isatoic anhydrides with arylboronic acids

The decarboxylative coupling of isatoic anhydrides with arylboronic acids was realized for the first time in the presence of Pd2(dba) 3 and DPEphos, achieving aryl o-aminobenzoates with yields ranging from moderate to good. The efficiency of this procedure was demonstrated by good compatibility with fluoro, chloro, bromo, nitro, cyano, trifluoromethyl, formacyl, acetyl, thienyl, and naphthyl groups. Preliminary mechanistic experiments using deuterium labeling showed that the oxygen atom was derived from dioxygen.

APPLICATION OF THE PHOTO-FRIES REARRANGEMENT OF ARYL N-CHLOROACETYLANTHRANYLATES AS KEY STEP IN THE SYNTHESIS OF 5-(2-HYDROXYPHENYL)-1,3-DIHYDRO-2H-1,4-BENZODIAZEPIN-2-ONES

Condensation of isatoic anhydride with phenols, followed by treatment of the resulting aryl anthranylates (4) with chloroacetyl chloride gives aryl N-chloroacetylanthranylates (5).Their uv-irradiation results in photo-Fries rearrangement, to afford benzophenones (6).Direct treatment of the latter with ammonia gives rise to 1,3-quinazolines (7); by contrast, treatment of 6 with potassium iodide and subsequently with ammonia leads to 1,3-dihydro-2H-1,4-benzodiazepin-2-ones (1).

SYNTHESIS, KINETICS AND MECHANISM OF CYCLIZATION OF 1-(2-ARYLOXYCARBONYLPHENYL)-3-PHENYLTRIAZENES

Twelve substituted 1-(2-aryloxycarbonylphenyl)-3-phenyltriazenes have been synthetized and kinetics of their reactions have been measured in 52.1percent (by mass) aqueous methanol at pH 3 to 11.Plots of kobs vs pH show three regions: noncatalyzed cyclization (pH 4 to 7), acid-catalyzed splitting of the triazene chain, and base-catalyzed cyclization.The non-catalyzed cyclization exhibits a kinetic isotope effect, the reaction constant Q = 2.69 (?p-), and β1g = 1.02, which indicates a mechanism of E1cB type with intramolecular proton transfer and a transient formation of a ketene intermediate.The base-catalyzed cyclization, on the other hand, exhibits the reaction constant Q = 1.05 (?p-), β1g = 0.4, and distinct steric effects, which indicates a cyclization by BAc2 mechanism with rate-limiting formation of the tetrahedral intermediate.