89114-62-5Relevant academic research and scientific papers
Synthesis of diaryl ethers, diaryl thioethers, and diarylamines mediated by potassium fluoride-alumina and 18-crown-6: Expansion of scope and utility
Sawyer, J. Scott,Schmittling, Elisabeth A.,Palkowitz, Jayne A.,Smith III, William J.
, p. 6338 - 6343 (2007/10/03)
An efficient alternative to the Ullmann ether synthesis of diaryl ethers, diaryl thioethers, and diarylamines involving the S(N)Ar addition of a phenol, thiophenol, or aniline to an appropriate aryl halide, mediated by potassium-fluoride alumina and 18-crown-6 in acetonitrile or DMSO, is described. Expansion of the reaction conditions to include DMSO as solvent has resulted in a far greater range of substitution patterns permitted on the electrophile. For example, it was found that electronically unfavorable 3- chlorobenzonitrile could be condensed with 3-methoxyphenol to form the corresponding diaryl ether in 66% yield, a combination not normally amenable to Ullmann coupling. Electron-withdrawing groups present on the electrophile may be as diverse as nitro, cyano, formyl, acetyl, ester, amide, and even aryl. The method features a simple reaction procedure that provides products in generally good to excellent purified yields.
POTENTIAL ANTIDEPRESSANTS: 2-(METHOXY- AND HYDROXY-PHENYLTHIO)BENZYLAMINES AS SELECTIVE INHIBITORS OF 5-HYDROXYTRYPTAMINE RE-UPTAKE IN THE BRAIN
Jilek, Jiri,Sindelar, Karel,Pomykacek, Josef,Kmonicek, Vojtech,Sedivy, Zdenek,et al.
, p. 3294 - 3338 (2007/10/02)
2-, 3- and 4-Methoxythiophenol, and 2,4-, 2,5- and 3,4-dimethoxythiophenol were transformed in two steps to the corresponding 2-(methoxyphenylthio)benzoyl chlorides XIII which were reacted with ammonia, methylamine, dimethylamine, diethylamine, dipropylamine, and di(2-propyl)amine to give the amides XIV-XIX.These were reduced mostly with lithium aluminium hydride to the amines II-VII.These methoxylated amines were demethylated mostly either by heating with pyridine hydrochloride or by treatment with boron tribromide.Some of the 2-(methoxy- and hydroxy-phenylthio)benzylamines prepared, especially compounds II, III, XXI, and XXII, indicated properties of potential antidepressants being highly active and selective inhibitors of 5-hydroxytryptamine re-uptake in the brain structures and having the typical antireserpine activity.The most interesting compound of the series is XXIb (hydrogen maleate VUFB-15 468) which is undergoing preclinical studies.On the basis of its structure, some further compounds (XXVII-XXIX, XXXIX-XLI) were prepared by various methods.
PHOTOCHEMISTRY OF HYDROXAMIC ACIDS
Hosangadi, B.D.,Chhaya, P.N.,Nimbalkar, M.M.,Patel, N.R.
, p. 5375 - 5380 (2007/10/02)
Photochemical reactions of hydroxamic acids have been studied.The intermediacy of a RCONH(.) radical is postulated, based on oxidations achieved with DCA under photochemical conditions.
PHOTOCHEMICAL REACTIONS OF BENZOHYDROXAMIC ACIDS
Chhaya, Pradeep,Nimbalkar, Manmohan,Hosangadi, Bhaskar
, p. 5551 - 5552 (2007/10/02)
2-(Arylthio)benzohydroxamic acids 1 and 2 undergo photodeoxygenation under unsensitised irradiations.DCA sensitized irradiation of a model benzohydroxamic acid (5), however, yields 1,2-diacyldiazine (6).
