63167-04-4Relevant academic research and scientific papers
Sequential C-H activation enabled expedient delivery of polyfunctional arenes
Cai, Xiaoqing,Chen, Qian,Chen, Xiaojian,Gao, Yang,Huo, Yanping,Li, Xianwei,Ouyang, Wensen,Rao, Jianhang,Wang, Jie
, p. 8075 - 8078 (2021/08/20)
Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C-H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction of biologically active molecules, such as Bipenamol.
Ortho-position imine ester or cyano substituted aryl thioether derivative, and preparation method and application thereof
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Paragraph 0169-0172, (2020/06/17)
The invention belongs to the technical field of organic synthesis, and particularly relates to an ortho-position imine ester or cyano substituted aryl thioether derivative, and a preparation method and an application thereof. The structural formula of the ortho-position imine ester or cyano substituted aryl thioether derivative is represented by formula (I) or formula (I'). The preparation methodcomprises the following steps: selecting an imine ester substrate and different substituted disulfide coupling reagents, mixing the reactants with a catalyst, an oxidant and a halide ion capturing agent under air atmosphere and alkaline conditions, and carrying out an aromatic ring ortho-position carbon-hydrogen bond activation reaction to obtain the ortho-position imine ester or cyano substitutedaryl sulfide derivative. The preparation method is simple and easily available in substrate and simple to operate, and achieves the efficient synthesis of the aryl thioether derivative of ortho-position imine ester or cyano group through the regulation of a catalytic system; and the product can be applied to later-stage derivatization reaction of drug molecules such as probenecid, and synthesis potential is provided for rapid construction of thioether derivatives with bioactive molecule libraries.
POTENTIAL ANTIDEPRESSANTS: 2-(PHENYLTHIO)ARALKYLAMINE
Jilek, Jiri,Urban, Jiri,Taufmann, Petr,Holubek, Jiri,Dlabac, Antonin,et al.
, p. 1995 - 2008 (2007/10/02)
Reactions of 2-(phenylthio)benzyl chloride with dimethylamine, diethylamine, pyrrolidine, piperidine, morpholine, and 1-methylpiperazine afforded the title compounds VI-XI.Reaction of 2-(phenylthio)benzaldehyde with nitromethane gave the nitrostyrene XIV which was reduced with lithium aluminium hydride to 2-(2-phenylthio)phenyl)ethylamine (XVI).This was transformed to the N-methyl and N,N-dimethyl derivatives XVIII and XIX.The Claisen reaction of (2-(2-phenylthio)phenyl)acetonitrile with ethyl acetate afforded the compound XXI which was cleaved by phosphoric acid to (2-(phenylthio)phenyl)acetone (XX).The Leuckart-Wallach reaction afforded the formamide XXIII which was used as starting material for preparing the amines XXIV-XXVI.The alternative approach to these compounds starting by reaction of the aldehyde XII with nitroethane was complicated by the fact that in addition to the nitropropene XV 2-(phenylthio)benzonitrile was also formed.The synthetic use of the inhomogenous XV resulted then in mixtures of amines XXIV-XXVI with IV-VI which was followed by means of mass and 1H NMR spectra.The amines XXIV-XXVI were oxidized to the sulfoxides XXVII-XXIX.The oily bases were transformed to crystalline salts and spectra of all homogeneous bases were recorded.Pharmacological testing showed the amine VI (VUFB-15370) to be a promising potential antidepressant.The amines XI and XXV showed also pharmacological profile of potential antidepressant.
