520-03-6Relevant articles and documents
Defined Palladium-Phthalimidato Catalysts for Improved Oxidative Amination
Martínez, Claudio,Mu?iz, Kilian
, p. 7367 - 7370 (2016)
New palladium(II)-phthalimidato complexes have been synthesized, isolated, and structurally characterized. As demonstrated from over 30 examples, they constitute superior catalysts for oxidative amination reactions of alkenes with phthalimide as the nitrogen source. This work streamlines vicinal difunctionalization of alkenes and provides access to significantly improved and experimentally simplified synthetic protocols.
Palladium-Catalyzed Carbonylative Dearomatization of Indoles
Wang, Hai,Wu, Xiao-Feng
, p. 5264 - 5268 (2019)
An interesting palladium-catalyzed dearomative carbonylation of N-(2-bromobenzoyl)indoles has been developed. The catalytic system is composed of commercially available Pd(OAc)2 and DPPP and uses alcohols and anilines as nucleophiles to afford moderate to good yields of the desired products. This method provides a straightforward access to diverse fused indoline esters and amides with good functional group tolerance. Remarkably, this is the first example of carbonylative dearomatization.
Photoinduced reactions of 1,3,4(2H)-isoquinolinetriones with diphenylacetylenes - An efficient one pot syntheses of dibenz[de,g]-(2H)-isoquinoline-4, 6-dione derivatives
Zhang,Qian,Fun,Xu
, p. 8141 - 8145 (2000)
Photoinduced reactions of 1,3,4(2H)-isoquinolinetriones with diphenylacetylenes afforded the corresponding dibenz[de,g]-(2H)-isoquinoline-4,6-dione derivatives in moderate to high yields via a reaction sequence involving [2+2] photocycloaddition, ring opening rearrangement of the oxetene intermediate and dehydrogenative cyclization in one pot. (C) 2000 Elsevier Science Ltd.
Improved synthesis of pyridazinediones under microwave irradiation
Bourel, Line,Tartar, Andre,Melnyk, Patricia
, p. 4145 - 4148 (1996)
Pyridazinediones have been synthesized with good to excellent yields under microwave irradiation. The results were compared with traditional stirring.
Mechanistic Studies of Ullmann-Type C–N Coupling Reactions: Carbonate-Ligated Copper(III) Intermediates
Gurjar, Kamlesh K.,Sharma, Rajendra K.
, p. 862 - 869 (2017)
In Ullmann-type C?N coupling reactions, the involvement of CuIII species has been proposed many times on the basis of the oxidative addition–reductive elimination (OA-RE) path for these reactions, but actual species could not be traced in experimental studies. In the C?N coupling reactions, carbonate and phosphate were considered widely as bases. In the present study, Cu-mediated C?N coupling reactions of aryl halides and NuNH (amide and imide) were investigated extensively, and we provide direct spectroscopic evidence of actual CuIII species. For the first time, we reveal that carbonate and phosphate ions act as bidentate ligands as well as a base in the catalytic cycle, and thus the actual intermediate species is a carbonate- or phosphate-ligated, distorted octahedral CuIII complex. Our experimental and computational studies have strengthened the hypothesis that these reactions follow an OA-RE path.
Visible-Light-Induced Controlled Oxidation of N-Substituted 1,2,3,4-Tetrahydroisoquinolines for the Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones and Isoquinolin-1(2H)-ones
Bansode, Ajay H.,Suryavanshi, Gurunath
supporting information, p. 1390 - 1400 (2021/01/26)
A visible light-rose bengal-TBHP mediated, controlled oxidation of N-substituted 1,2,3,4-tetrahydroisoquinolines is developed for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones and isoquinolin-1(2H)-ones. The present method feature's a broad substrate scope, good functional group tolerances, and the products were prepared in good to excellent yields. The developed methodology further demonstrated in the synthesis of isoindolo[2,1-b] isoquinolin-5(7H)-one (topoisomerase-I inhibitor). (Figure presented.).
A phosphonium ylide as a visible light organophotoredox catalyst
Toda, Yasunori,Tanaka, Katsumi,Matsuda, Riki,Sakamoto, Tomoyuki,Katsumi, Shiho,Shimizu, Masahiro,Ito, Fuyuki,Suga, Hiroyuki
supporting information, p. 3591 - 3594 (2021/04/14)
A phosphonium ylide-based visible light organophotoredox catalyst has been designed and successfully applied to halohydrin synthesis using trichloroacetonitrile and epoxides. An oxidative quenching cycle by the ylide catalyst was established, which was confirmed by experimental mechanistic studies.
Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams
Bai, Ya,Shi, Lingling,Zheng, Lianyou,Ning, Shulin,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao
supporting information, p. 2298 - 2302 (2021/04/05)
An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.
High-throughput tandem-microwell assay for ammonia repositions FDA-Approved drugs to inhibit Helicobacter pylori urease
Fang, Houqin,Huang, Shengshuo,Li, Fangzheng,Liao, Lujian,Liu, Fan,Liu, Qi,Wu, Fang,Wu, Xin-Yan,Xiao, Zhuping,Xu, Jinyi,Yu, Jing,Zhang, Yan-Xia,Zhou, Yueyang
, (2021/11/01)
To date, little attempt has been made to develop new treatments for Helicobacter pylori (H. pylori), although the community is aware of the shortage of treatments for H. pylori. In this study, we developed a 192-tandem-microwell-based high-throughput assay for ammonia that is a known virulence factor of H. pylori and a product of urease. We could identify few drugs, that is, panobinostat, dacinostat, ebselen, captan, and disulfiram, to potently inhibit the activity of ureases from bacterial or plant species. These inhibitors suppress the activity of urease via substrate-competitive or covalent-allosteric mechanism, but all except captan prevent the antibiotic-resistant H. pylori strain from killing human gastric cells, with a more pronounced effect than acetohydroxamic acid, a well-known urease inhibitor and clinically used drug for the treatment of bacterial infection. This study offers several bases for the development of new treatments for urease-containing pathogens and to study the mechanism responsible for the regulation of urease activity.
“On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides
Wen, Xiaowei,Liu, Xiaojuan,Yang, Zhiqi,Xie, Menglan,Liu, Yuxi,Long, Lipeng,Chen, Zhengwang
supporting information, p. 1738 - 1743 (2021/03/14)
An efficient nano-Cu2O-catalyzed cascade multicomponent reaction of 2-halobenzoic acids and trimethylsilyl cyanide with diverse amines was developed using water as a solvent, affording versatileN-substituted phthalimide derivatives in moderate to excellent yields. This novel strategy features carbon monoxide gas-free, environmentally benign, one-pot multistep transformation, commercially available reagents, a cheap catalyst without any additives, wide functional group tolerance, and operational convenience.
