A practical and scalable synthesis route of acetylphenylboronic acids is described. Bromoacetophenones(compounds 3a, 3b) were ketalized with ethylene glycol and triethyl orthoformate to give bromo ketals(compounds 4a_...A practical and scalable synthesis route of acetylphenylboronic acids is described. Bromoacetophenones(compounds 3a, 3b) were ketalized with ethylene glycol and triethyl orthoformate to give bromo ketals(compounds 4a_4c) in 60_80% yields. Compounds 4a_4b were treated with a Grignard reagent and then exchanged with borate to give p- and m-acetylphenyl boronic acids(compounds 5a and 5b) in 80% and 56% yields, respectively. The o-form(compound 5c) was obtained in 61% yield via the BuLi method.展开更多
A new spectrophotometric method was developed for the determination of aminomethylbenzoic acid （PAMBA） using 7,7,8,8-tetracyanoquinodimethane （TCNQ）. The method was based on the formation of charge transfer （CT）...A new spectrophotometric method was developed for the determination of aminomethylbenzoic acid （PAMBA） using 7,7,8,8-tetracyanoquinodimethane （TCNQ）. The method was based on the formation of charge transfer （CT） complex of this drug as n-electron donor with the n-acceptor TCNQ. TCNQ was found to react with PAMBA to produce a kind of yellow complex. The CT reaction proceeded quantitatively in pH 8.5 buffer solution. Different variables affecting the reaction were carefully studied and optimized. Under optimal reaction conditions, the stoichiometric ratio of the reaction, maximum absorption wavelength and the value of molar absorptivity were measured to be 1 ： 1, 425 nm, and 1.9 × 10^4 L.mol ^-1.cm^-1, respectively. Beer＇s law was obeyed in the range of 1- 9 μgomL-1 of PAMBA. The data have been filled to a linear regression equation A= -0.2612＋0.1123c （μgomL^-1）, with a correlation coefficient of 0.9996. The detection limit was 0.4 μg·mL^-1, R,S.D. was less than 1.9%, and average recovery was over 97.6%. The formation of the CT complex was also confirmed by both infrared and 1H NMR measurements. The thermodynamic property, kinetic property and reaction mechanism have also been discussed. The method developed was applied successfully to the determination of the subject drug in its pharmaceutical dosage forms with good precision and accuracy compared to official method revealed by t- and F-tests.展开更多
基金the National Nature Science Foundation of China(No.30 17110)
文摘A practical and scalable synthesis route of acetylphenylboronic acids is described. Bromoacetophenones(compounds 3a, 3b) were ketalized with ethylene glycol and triethyl orthoformate to give bromo ketals(compounds 4a_4c) in 60_80% yields. Compounds 4a_4b were treated with a Grignard reagent and then exchanged with borate to give p- and m-acetylphenyl boronic acids(compounds 5a and 5b) in 80% and 56% yields, respectively. The o-form(compound 5c) was obtained in 61% yield via the BuLi method.
基金Project supported by the National Natural Science Foundation of China （No. 21076138） and the Natural Science Foundation of Shanxi Institution of Higher Education （No. 20080025）.
文摘A new spectrophotometric method was developed for the determination of aminomethylbenzoic acid （PAMBA） using 7,7,8,8-tetracyanoquinodimethane （TCNQ）. The method was based on the formation of charge transfer （CT） complex of this drug as n-electron donor with the n-acceptor TCNQ. TCNQ was found to react with PAMBA to produce a kind of yellow complex. The CT reaction proceeded quantitatively in pH 8.5 buffer solution. Different variables affecting the reaction were carefully studied and optimized. Under optimal reaction conditions, the stoichiometric ratio of the reaction, maximum absorption wavelength and the value of molar absorptivity were measured to be 1 ： 1, 425 nm, and 1.9 × 10^4 L.mol ^-1.cm^-1, respectively. Beer＇s law was obeyed in the range of 1- 9 μgomL-1 of PAMBA. The data have been filled to a linear regression equation A= -0.2612＋0.1123c （μgomL^-1）, with a correlation coefficient of 0.9996. The detection limit was 0.4 μg·mL^-1, R,S.D. was less than 1.9%, and average recovery was over 97.6%. The formation of the CT complex was also confirmed by both infrared and 1H NMR measurements. The thermodynamic property, kinetic property and reaction mechanism have also been discussed. The method developed was applied successfully to the determination of the subject drug in its pharmaceutical dosage forms with good precision and accuracy compared to official method revealed by t- and F-tests.
