205533-30-8Relevant articles and documents
Synthesis and biological activity of polyfluorinated p-aminosalicylic acids and their amides
Burgart, Yanina V.,Saloutin, Victor I.,Shchegolkov, Evgeny V.,Shchur, Irina V.
, p. 636 - 638 (2020/10/09)
Polyfluorinated analogues of salicylamide and p-aminosalicylic acid have been synthesized based on methyl polyfluorosalicylates. Polyfluorosalicylamides were obtained by the reaction with aqueous ammonia, while 4-aminopolyfluorosalicylic acids were prepar
A convenient and efficient approach to polyfluorosalicylic acids and their tuberculostatic activity
Shchegol'Kov, Evgeny V.,Shchur, Irina V.,Burgart, Yanina V.,Saloutin, Victor I.,Solodnikov, Sergey Yu.,Krasnykh, Olga P.,Kravchenko, Marionella A.
, p. 2455 - 2458 (2016/07/07)
We have developed the practical method for polyfluorosalicylic acids synthesis via nucleophilic ortho-mono-substitution of fluorine atom with magnesium methoxide. We have managed to increase the yield of targeted polyfluorosalicylic acids from good to quantitative. We have studied the tuberculostatic activity of polyfluorosalicylic acids. It has been found that minimum inhibitory concentration (MIC) of compounds is from 0.7 to 6.5 μg/mL depending on the structure.
The regioexhaustive functionalization of difluorophenols and trifluorophenols through organometallic intermediates
Marzi, Elena,Gorecka, Joanna,Schlosser, Manfred
, p. 1609 - 1618 (2007/10/03)
2,4-Difluorophenol, 2,5-difluorophenol, 2,3-difluorophenol, 3,5-difluorophenol, 3,4-difluorophenol, 2,4,5-trifluorophenol and 2,3,4-trifluorophenol were converted into all 18 possible di- or trifluorinated hydroxybenzoic acids (1a-c, 4a-c, 9a-c, 12a,b, 14a-c, 17a,b, 18a,b), all of them new compounds. The phenolic hydrogen atom was replaced by a methoxymethyl or, less frequently, by a triisopropylsilyl group, which exerted an ortho activating or ortho shielding effect, respectively. Sites flanked by two electronegative substituents (fluorine, alkoxy) were deprotonated with particular ease. They had to be silenced by the reversible attachment of a metalation-blocking trimethylsilyl group or of a metalation-deflecting chlorine atom if the metal was to be introduced elsewhere. In all cases but one, the stage was thus set for an intramolecular competition between metalation at an oxygen-adjacent or a fluorine-adjacent site. It proved indeed possible to secure the desired regioflexibility in either way by relying on an appropriate substrate-reagent matching. This demonstrates once more the potential of the organometallic approach to diversity-oriented synthesis.
