90408-20-1Relevant academic research and scientific papers
Ruthenium(ii)-catalyzed decarbonylative and decarboxylative coupling of isatoic anhydrides with salicylaldehydes: access to aryl 2-aminobenzoates
Bora, Bidisha R.,Prakash, Rashmi,Sultana, Sabera,Gogoi, Sanjib
, p. 2725 - 2730 (2021/04/07)
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
Lu, Wei,Chen, Jiuxi,Liu, Miaochang,Ding, Jinchang,Gao, Wenxia,Wu, Huayue
supporting information; experimental part, p. 6114 - 6117 (2012/01/06)
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.
SYNTHESIS, KINETICS AND MECHANISM OF CYCLIZATION OF 1-(2-ARYLOXYCARBONYLPHENYL)-3-PHENYLTRIAZENES
Pytela, Oldrich,Bahnik, Zdenek
, p. 2692 - 2700 (2007/10/02)
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.
