58202-86-1Relevant academic research and scientific papers
Highly ortho-Selective Chlorination of Anilines Using a Secondary Ammonium Salt Organocatalyst
Xiong, Xiaodong,Yeung, Ying-Yeung
supporting information, p. 16101 - 16105 (2016/12/26)
An organocatalytic, highly facile, efficient, and regioselective ortho-chlorination of anilines is described. A secondary ammonium chloride salt has been employed as the catalyst and the reaction can be conducted at room temperature without protection from air and moisture. In addition, the reaction is readily scalable and the catalyst can be recycled and reused. This catalytic protocol has been applied to the efficient synthesis of a highly potent c-Met kinase inhibitor. Mechanistic studies revealed that unique structural features of the secondary ammonium chloride salt are important for both the catalysis and regioselectivity of the electrophilic ortho-chlorination.
Pd-catalyzed synthesis of functionalized arylketones from boronic acids and carboxylic acids activated in situ with dimethyl dicarbonate
Goo?en, Lukas J.,Winkel, Lars,D?hring, Arno,Ghosh, Keya,Paetzold, Jens
, p. 1237 - 1240 (2007/10/03)
Highly efficient catalyst systems were developed that allow the palladium-catalyzed cross-coupling of arylboronic acids with carboxylic acids activated in situ with dimethyl dicarbonate at room temperature. As byproducts, only methanol, CO2, an
Preparation of m-acylaniline derivatives by the reaction of tricarbonyl(cyclohexadienone O-benzyloxime)iron complex and higher order cuprates
Ban, Soo Ho,Hayashi, Yujiro,Narasaka, Koichi
, p. 393 - 394 (2007/10/03)
Reaction of tricarbonyl[(2,3,4,5-η)-2,4-cyclohexadien-1-one O-benzyloxime]iron and organocuprates, followed by the treatment with acetic anhydride and carbon monoxide, affords [(1,2,3,4-η)-1-(N-acetoxy-N-benzyloxyamino)-5-endo-acyl-1,3-cyclohexadiene] tri
Reinvestigation of a 5H-Dibenzotriazonine Synthesis
Peet, Norton P.,Sunder, Shyam,Barbuch, Robert J.,Whalon, Michael R.,Huber, Edward W.,Huffman, John C.
, p. 1611 - 1618 (2007/10/02)
Treatment of 5-chloro-2-aminobenzophenone (1) with o-phenylenediamine, sodium acetate, and acetic acid gave 2-(acetyl)amino-5-chlorobenzophenone (5) rather than N--1,2-benzenediamine (3), as reported by Kulkarni et al.Authentic 3 was prepared and treated with chloroacetic acid and polyphosphoric acid (PPA) to give 1, recovered 3, 2,8-dichloro-6,12-diphenyldibenzodiazocine (9) and 2-chloro-6-(chloromethyl)-13-phenyl-5H-dibenzotriazonine (10).Treatment of 5 with PPA, with or without chloroacetic acid, gave phenyl> phenylmethanone (11) as the sole product in 90percent yield.Treatment of other benzophenones, acetophenones, and anilines with sodium acetate and acetic acid provided acetanilides in 78-96percent yield, with the exception of 2'-aminoacetophenone (20), wich gave a quantitative yield of 2--4-methylquinoline (21).The mechanism of acetanilide formation with sodium acetate and acetic acid is discussed.The structure of 21 was established using high resolution 1H nmr techniques.Attempts to prepare an authentic sample of 21 from 2-chlorolepidine (26) and (20) gave 4-methyl-N--2-quinolinamine (29) as the major product.
