6550-67-0Relevant academic research and scientific papers
Polysubstituted Indole Synthesis via Palladium/Norbornene Cooperative Catalysis of Oxime Esters
Liu, Jiechun,Lin, Haojiang,Jiang, Huanfeng,Huang, Liangbin
supporting information, p. 484 - 489 (2022/01/20)
Polysubstituted indoles are prevalent in pharmaceuticals, agrochemicals, and organic materials. Presented herein is the fact that polyfunctionalized indoles can be efficiently constructed from easily accessible oxime esters and aryl iodides, involving a palladium/norbornene synergistic synthesis. The reaction is enabled by a unique class of electrophiles in palladium/norbornene cooperative catalysis, which are oxime esters derived from simple ketone. The broad substrate scope and high functional group tolerance could make this method attractive for the synthesis of polysubstituted indoles.
Method for synthesizing 2-substituted indole compound from iodobenzene and oxime ester under catalysis of palladium
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Paragraph 0374-0381, (2022/01/05)
The invention belongs to the technical field of organic chemistry, and discloses a method for synthesizing a 2-substituted indole compound from iodobenzene and oxime ester under the catalysis of palladium. The method comprises the following steps of reacting an oxime ester compound with iodobenzene under the action of a palladium catalyst, a phosphine ligand and norbornene by taking an organic solvent as a reaction medium in a protective atmosphere, and carrying out subsequent treatment to obtain the 2-substituted indole compound. According to the method, palladium is used as a catalyst, the phosphine ligand is adopted, the yield is high, and the substrate applicability is wide. In addition, the oxime ester compound is used as a raw material, and the method has the advantages of cheap and easily-prepared raw materials, simple operation, mild reaction conditions and the like.
A Mild Approach for the Synthesis of Indoles from N -(2-Iodo-aryl)formAamides and Phenylacetylene by a Copper(I)- and Palladium-Catalyzed Cascade Process
Ahmed, Atiur,Ghosh, Munmun,Dhara, Shubhendu,Ray, Jayanta K.
, p. 2455 - 2458 (2015/07/27)
An efficient one-pot copper(I)- and palladium-catalyzed synthesis of indoles from N-(2-iodo-aryl)formamides and phenylAacetylene is described. The cascade reaction comprises a Sonogashira cross-coupling, an intramolecular C-N bond formation, and hydrolysi
2-phenylindole and arylsulphonamide: Novel scaffolds bactericidal against mycobacterium tuberculosis
Naik, Maruti,Ghorpade, Sandeep,Jena, Lalit Kumar,Gorai, Gopinath,Narayan, Ashwini,Guptha, Supreeth,Sharma, Sreevalli,Dinesh, Neela,Kaur, Parvinder,Nandishaiah, Radha,Bhat, Jyothi,Balakrishnan, Gayathri,Humnabadkar, Vaishali,Ramachandran, Vasanthi,Naviri, Lava Kumar,Khadtare, Pallavi,Panda, Manoranjan,Iyer, Pravin S.,Chatterji, Monalisa
supporting information, p. 1005 - 1009 (2014/12/10)
A cellular activity-based screen on Mycobacterium tuberculosis (Mtb) H37Rv using a focused library from the AstraZeneca corporate collection led to the identification of 2-phenylindoles and arylsulphonamides, novel antimycobacterial scaffolds. Both the series were bactericidal in vitro and in an intracellular macrophage infection model, active against drug sensitive and drug resistant Mtb clinical isolates, and specific to mycobacteria. The scaffolds showed promising structure-activity relationships; compounds with submicromolar cellular potency were identified during the hit to lead exploration. Furthermore, compounds from both scaffolds were tested for inhibition of known target enzymes or pathways of antimycobacterial drugs including InhA, RNA polymerase, DprE1, topoisomerases, protein synthesis, and oxidative-phosphorylation. Compounds did not inhibit any of the targets suggesting the potential of a possible novel mode of action(s). Hence, both scaffolds provide the opportunity to be developed further as leads and tool compounds to uncover novel mechanisms for tuberculosis drug discovery.
Oxidation of 2-arylindoles for synthesis of 2-arylbenzoxazinones with oxone as the sole oxidant
Lian, Xiao-Li,Lei, Hao,Quan, Xue-Jing,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
supporting information, p. 8196 - 8198 (2013/09/12)
A novel and efficient method for the oxidation of 2-arylindoles to synthesize 2-arylbenzoxazinones utilizing oxone as the sole oxidant has been developed. The reaction tolerates a wide range of functional groups and allows quick and atom-economical assembly of a variety of valuable 2-arylbenzoxazinones in high yields.
The sequential reactions of tetrazoles with bromoalkynes for the synthesis of (Z)-N-(2-bromo-1-vinyl)-N-arylcyanamides and 2-arylindoles
Zhang, Jiajun,Meng, Ling-Guo,Li, Pinhua,Wang, Lei
, p. 6807 - 6812 (2013/05/23)
2-Arylindoles were prepared by a sequential reaction of Ag-catalyzed α-addition-Pd-catalyzed C-H bond functionalization of tetrazoles with bromoalkynes. A stereocontrolled Ag-catalyzed α-addition reaction of tetrazoles with bromoalkynes underwent smoothly to generate (Z)-N-(2-bromo-1- vinyl)-N-arylcyanamides, which were subsequently converted into 2-arylindoles through an intramolecular cyclization by Pd-catalyzed direct C-H bond functionalizations.
2,3-disubstituted indoles via palladium-catalyzed reaction of 2-alkynyltrifluoroacetanilides with arenediazonium tetrafluoroborates
Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Perboni, Alcide,Sferrazza, Alessio,Stabile, Paolo
supporting information; experimental part, p. 3279 - 3281 (2010/10/02)
(Figure Presented) A novel palladium-catalyzed synthesis of free N-H 2,3-disubstituted indoles from arenediazonium tetrafluoroborates and 2-alkynyltrifluoroacetanilides is presented. The reaction tolerates a variety of useful substituents both in the starting alkyne and the arenediazonium salt, including bromo and chloro substituents, nitro, cyano, keto, ester, and ether groups, as well as ortho substituents such as methoxy and methyl groups.
Pd PEPPSI-IPr-mediated reactions in metal-coated capillaries under MACOS: The synthesis of indoles by sequential aryl amination/heck coupling
Shore, Gjergji,Morin, Sylvie,Mallik, Debasis,Organ, Michael G.
, p. 1351 - 1356 (2008/09/17)
A method has been devised for the microwave-assisted, continuous-flow preparation of indole alkaloids by a two-step aryl amination/cross-coupling sequence of bromoalkenes and 2-bromoanilines. This process requires both the presence of a metal-lined flow tube (a 1180 micron capillary) and the Pd PEPPSI-IPr catalyst; without either, the catalyst or the film, there is zero turnover of this catalytic process. A silver film has been shown to provide some conversion (48-62%), but optimal results (quantitative) across a variety of bromoalkenes and bromoanilines were achieved by using a highly porous palladium film. Possible roles for the Pd film are considered, as is the interplay of the catalyst and the film.
