809274-63-3Relevant academic research and scientific papers
Synthesis of Multibromo-Substituted Quinolines by NBS-Mediated Cascade Electrophilic Bromination/Cyclization of N -(3-Phenylprop-2-ynyl)anilines
Deng, Si,Ouyang, Wenliang,Bai, Jiang,Song, Xian-Rong,Yang, Ruchun,Xiao, Qiang
, p. 2469 - 2476 (2021)
A new and convenient protocol is presented here for the synthesis of 3,6,8-tribromoquinolines via cascade cyclization of N -(3-phenylprop-2-ynyl)anilines employing N -bromosuccinimide as an electrophile. The metal-free process is carried out under mild conditions and is compatible with a variety of substituents. The Sonogashira coupling reaction regioselectively occurs at position C-6 of the obtained products.
Heterocyclic Iodoniums for the Assembly of Oxygen-Bridged Polycyclic Heteroarenes with Water as the Oxygen Source
Zhu, Daqian,Wu, Zhouming,Luo, Bingling,Du, Yongliang,Liu, Panpan,Chen, Yunyun,Hu, Yumin,Huang, Peng,Wen, Shijun
, p. 4815 - 4818 (2018/08/24)
A diverse set of novel heterocyclic iodoniums was synthesized for the first time. The reactions of these unique iodoniums with environmentally benign water as the oxygen source provided structurally complex oxygen-incorporated heteropolycycles that are essential motifs in natural products and biologically active compounds. The transformation only required low-cost copper acetate. Further derivatization of the obtained polycycles expanded the structural diversity, which is important in the building of chemical libraries for drug discovery.
Hypervalent iodine compound containing heterocyclic ring as well as preparation method and application thereof
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, (2019/01/08)
The invention discloses a hypervalent iodine compound containing a heterocyclic ring as well as a preparation method and application thereof. A structure of the compound is shown as a formula (I): theformula (I) is shown in the description, wherein R is selected from hydrogen, halogen, alkyl, alkoxy, halogenated alkyl, halogenated alkoxy, nitryl, cyano, hydroxyl or -COOR'; R' is alkyl or halogenated alkyl; and Het is substituted or non-substituted 1,4-benzopyranone, substituted or non-substituted quinolone, substituted or non-substituted isoquinoline, substituted or non-substituted thiobenzopyranone, substituted or non-substituted coumarin and substituted or non-substituted oxepin. The compound disclosed by the invention is novel in structure and is the hypervalent iodine compound containing the heterocyclic ring; the hypervalent iodine compound is stable in structure and simple in preparation method; and meanwhile, the hypervalent iodine compound has a very good inhibition effect onML-1 and MOLM-13 cells and has an extremely great application prospect on prevention and/or treatment effect on leukemia.
Preparation of 3-Iodoquinolines from N-Tosyl-2-propynylamines with Diaryliodonium Triflate and N-Iodosuccinimide
Sasaki, Teppei,Moriyama, Katsuhiko,Togo, Hideo
, p. 11727 - 11734 (2017/11/28)
4-Aryl and 4-alkyl substituted 3-iodoquinolines could be smoothly obtained in one pot by treating N-tosyl-2-propynylamines with diaryliodonium triflate in the presence of K3PO4 and a catalytic amount of CuCl at room temperature, followed by treatment with N-iodosuccinimide and BF3·OEt2 at 0 °C, and then NaOH in methanol solution. The product, 3-iodo-4-phenylquinoline was smoothly transformed into 4-phenylquinoline with zinc; 4-phenyl-3-toluenesulfenylquinoline with toluenethiol, K2CO3, and CuI; 4-phenyl-3-phenylethynylquinoline with the Sonogashira coupling reaction; 4-phenyl-3-styrylquinoline with the Heck coupling reaction; 3,4-diphenylquinoline with the Suzuki-Miyaura coupling reaction; 2-cyclohexyl-3-iodo-4-phenylquinoline with cyclohexanecarboxylic acid, Ag2CO3, and K2S2O8; and 3-iodo-2-(2′,5′-dioxan-1′-yl)-4-phenylquinoline with benzoyl peroxide in dioxane.
Synthesis of substituted quinolines by the electrophilic cyclization of n-(2-alkynyl)anilines
Zhang, Xiaoxia,Yao, Tuanli,Campo, Marino A.,Larock, Richard C.
supporting information; experimental part, p. 1177 - 1187 (2010/04/02)
A wide variety of substituted quinolines are readily synthesized under mild reaction conditions by the 6-endo-dig electrophilic cyclization of N-(2-alkynyl)anilines by ICl, I2, Br2, PhSeBr, and p-O2NC6H4SCl. The reaction affords 3-halogen-, selenium- and sulfur-containing quinolines in moderate to good yields in the presence of various functional groups. Analogous quinolines bearing a hydrogen in the 3-position have been synthesized by the Hg(OTf)2-catalyzed ring closure of these same alkynylanilines.
Synthesis of substituted quinolines by electrophilic cyclization of N-(2-alkynyl)anilines
Zhang, Xiaoxia,Campo, Marino A.,Yao, Tuanli,Larock, Richard C.
, p. 763 - 766 (2007/10/03)
(Chemical Equation Presented) Quinolines substituted in the 3-position by an iodo or phenylseleno group are readily prepared in good to excellent yields by the reaction of propargylic anilines with appropriate electrophiles under mild reaction conditions.
Synthesis of fused polycycles by 1,4-palladium migration chemistry
Huang, Qinhua,Campo, Marino A.,Yao, Tuanli,Tian, Qingping,Larock, Richard C.
, p. 8251 - 8257 (2007/10/03)
Novel palladium migration/arylation methodology for the synthesis of complex fused polycycles has been developed, in which one or more sequential Pd-catalyzed intramolecular migration processes involving C-H activation are employed. The chemistry works best with electron-rich aromatics, which is in agreement with the idea that these palladium-catalyzed C-H activation reactions parallel electrophilic aromatic substitution.
