64648-35-7Relevant academic research and scientific papers
Facile one-pot transformation of arenes into aromatic nitriles under metal-cyanide-free conditions
Tamura, Toshiyuki,Moriyama, Katsuhiko,Togo, Hideo
, p. 2023 - 2029 (2015/03/18)
Electron-rich arenes bearing methyl or methoxy groups on the aromatic ring were treated with dichloromethyl methyl ether and ZnBr2, and then with molecular iodine and aq. ammonia to give the corresponding aromatic nitriles in good yields. Using this method, febuxostat was efficiently prepared from 4-bromophenol in four steps. The method can be used for the preparation of aromatic nitriles from arenes in one pot under metal-cyanide-free conditions. Various electron-rich arenes could be effectively converted into the corresponding aromatic nitriles in good yields, by treatment with ZnBr2 and dichloromethyl methyl ether, followed by reaction with molecular iodine and aq. ammonia.
Oxidation of Aromatic Compounds. V. Oxidation of Substituted Benzonitriles and 2,4,6-Triaryl-1,3,5-Triazines in System HSO3F-PbO2
Rudenko,Salfetnikova,Vasil'ev
, p. 1447 - 1470 (2007/10/03)
Low-temperature oxidation of substituted benzonitriles by the system HSO3F-PbO2 proceeds with intermediate formation of cation-radicals and leads to substitution of hydrogen atoms of the methyl group or benzene ring. This reaction provides a route for preparation of chloromethylsubstituted benzonitriles, diarylmethanes, diaryls, arylfluorosulfonates and substituted benzamides with cyano groups. In the case of methyl derivatives of 2,4,6-triphenyl-1,3,5-triazine substitution of the first and then the second hydrogen atom of the same methyl group transforms it into hydroxy or chloromethyl group, or into the aldehyde function.
RADICAL-CATIONS OF METHYL-SUBSTITUTED BENZONITRILES
Rudenko, A. P.,Cheremisin, A. A.,Shchegoleva, L. N.,Detsina, A. N.,Zarubin, M. Ya.
, p. 1675 - 1684 (2007/10/02)
The chemical oxidation of a series of methylated derivatives of benzonitrile in fluorosulfonic acid containing lead oxide leads to the formation of paramagnetic particles characterized by preferential localization of the unpaired electron at the C2, C3, C5, and C6 ring atoms.A computational analysis within the scope of the unrestricted Hartree-Fock method in the INDO approximation indicates that the structure of the obtained particles is described best by structures corresponding to the addition of a proton at the unshared electron pair of the nitrogen atom inthe nitrile fragment of the radical-cations.
