104749-68-0Relevant articles and documents
Synthesis of 2-Acylindoles via Ag- and Cu-Catalyzed anti-Michael Hydroamination of β-(2-Aminophenyl)-α,β-ynones: Experimental Results and DFT Calculations
Rode, Navnath D.,Abdalghani, Issam,Arcadi, Antonio,Aschi, Massimiliano,Chiarini, Marco,Marinelli, Fabio
, p. 6354 - 6362 (2018/05/25)
β-(2-Aminophenyl)-α,β-ynones afforded 3-unsubstituted 2-acylindoles in good yields in the presence of 20 mol % AgOTf under (microwave) MW heating. The use CuOTf as a catalyst resulted in a similar reaction outcome, generally with a lower efficiency. This transformation represents the first example of 5-endo-dig cyclization of 2-alkynylanilines bearing an acyl group linked to the triple bond. By contrast with the previously reported gold-catalyzed reaction of β-(2-aminophenyl)-α,β-ynones, which resulted in the formation of dibenzo[1,5]diazocines through a sequential process triggered by an intermolecular hydroamination, a selective intramolecular anti-Michael hydroamination was observed in the present study by silver/copper catalysis. Density functional theory calculations on the Ag-catalyzed reaction revealed that the catalyst induces an electrostatic arrangement in the TS coherent with the experimentally observed cyclization.
Merger of Visible-Light Photoredox Catalysis and C-H Activation for the Room-Temperature C-2 Acylation of Indoles in Batch and Flow
Sharma, Upendra K.,Gemoets, Hannes P. L.,Schr?der, Felix,No?l, Timothy,Van Der Eycken, Erik V.
, p. 3818 - 3823 (2017/06/19)
A mild and versatile protocol for the C-H acylation of indoles via dual photoredox/transition-metal catalysis was established in batch and flow. The C-H bond functionalization occurred selectively at the C-2 position of N-pyrimidylindoles. This room-temperature protocol tolerated a wide range of functional groups and allowed for the synthesis of a diverse set of acylated indoles. Various aromatic as well as aliphatic aldehydes (both primary and secondary) reacted successfully. Interestingly, significant acceleration (20 to 2 h) and higher yields were obtained under micro flow conditions.
Direct C-2 acylation of indoles with toluene derivatives via Pd(II)-catalyzed C-H activation
Zhao, Yaping,Sharma, Upendra K.,Schr?der, Felix,Sharma, Nandini,Song, Gonghua,Van Der Eycken, Erik V.
, p. 32559 - 32563 (2017/07/07)
A simple and efficient Pd-catalyzed method for the C2-acylation of indoles is described. Less toxic, stable, and commercially available toluene derivatives were used as acyl sources, with tert-butylhydroperoxide (TBHP) as oxidant and pivalic acid as addit
Reaction of 3-(2-nitrophenyl)-1-arylprop-2-en-1-ones with triethylphosphite in microwave revisited: One-pot synthesis of 2-aroylindoles and 2-arylquinolines
Gupta, Annah,Khajuria, Rajni,Kapoor, Kamal K.
supporting information, p. 31 - 38 (2016/01/09)
One-pot synthesis of 2-aroylindoles and 2-arylquinolines has been achieved by the reductive cyclization of 3-(2-nitrophenyl)-1-arylprop-2-en-1-ones with triethylphosphite [P(OEt)3] under microwave irradiation. The formation of 2-arylquinolines by this method is unprecedented.
Selective synthesis of quinolines and indoles: Sulfur-assisted or selenium-catalyzed reaction of β-(2-nitrophenyl)-α, β-unsaturated ketones with carbon monoxide
Umeda, Rui,Kouno, Hiroshi,Kitagawa, Takayuki,Okamoto, Tomohiro,Kawashima, Keisuke,Mashino, Tsukasa,Nishiyama, Yutaka
, p. 698 - 703 (2015/02/05)
A simple and selective synthetic method of quinolines and indoles by the reaction of β- (2-nitrophenyl)-α,β-unsaturated ketones with carbon monoxide was developed. When β-(2-nitrophenyl)- α,β-unsaturated ketones were allowed to react with carbon monoxide and water in the presence of a stoichiometric amount of sulfur or a catalytic amount of selenium, the corresponding quinolines were produced in moderate-to-good yields. On the other hand, in the absence of water, the indoles were produced by the selenium-catalyzed reaction of the β-(2-nitrophenyl)- α,β-unsaturated ketones with carbon monoxide.
Iodine-mediated intramolecular amination of ketones: The synthesis of 2-acylindoles and 2-acylindolines by tuning N-protecting groups
Gao, Wen-Chao,Jiang, Shan,Wang, Ruo-Lin,Zhang, Chi
, p. 4890 - 4892 (2013/07/05)
A general method for constructing both 2-acylindoles and 2-acylindolines via I2-mediated intramolecular C-N bond formation is presented, and the selective formation of either 2-acylindoles or 2-acylindolines just depends on the nitrogen protecting groups used in the same substrate skeletons. The Royal Society of Chemistry.
Synthesis of indoles through highly efficient cascade reactions of sulfur ylides and N-(ortho-chloromethyl)aryl amides
Yang, Qing-Qing,Xiao, Cong,Lu, Liang-Qiu,An, Jing,Tan, Fen,Li, Bin-Jie,Xiao, Wen-Jing
supporting information, p. 9137 - 9140 (2012/10/29)
Batting the ylides: A simple procedure carried out under mild conditions allows the direct and efficient synthesis of structurally diverse indoles. This approach involves a cascade reaction of sulfur ylides and N-(ortho-chloromethyl) aryl amides (see scheme). Copyright
A practical synthesis of 2-aroylindoles from N-(2-formylphenyl)trifluoro- acetamides in PEG-400
Zhao, Yu,Li, Deyao,Zhao, Liwen,Zhang, Jiancun
, p. 873 - 880 (2011/04/26)
A one-pot and environmentally benign approach to the synthesis of highly functionalized 3-unsubstituted 2-aroylindoles is described. Moderate to good yields were obtained through the reaction of easily accessible N-(2-formylphenyl)trifluoroacetamides and
Palladium-catalyzed domino C,N-coupling/carbonylation/suzuki coupling reaction: An efficient synthesis of 2-aroyl-/heteroaroylindoles
Arthuls, Martin,Pontikis, Renee,Florent, Jean-Claude
supporting information; experimental part, p. 4608 - 4611 (2009/12/09)
A convenient one-pot synthesis of 2-aroylindoles using a domino palladium-catalyzed C,N-coupllng/carbonylatlon/C,C-coupling sequence Is described. The reaction Involved easily prepared 2-gem-dibromovinylanilines and boronic acids under carbon monoxide. Op
Synthesis of 2- and 3-benzoylindoles by Friedel-Crafts reaction of indole-2,3-dicarboxylic anhydrides with anisoles
Miki, Yasuyoshi,Tsuzaki, Yasuhiko,Kai, Chika,Hachiken, Hiroko
, p. 1635 - 1643 (2007/10/03)
Reaction of 1-benzylindole-2,3-dicarboxylic anhydride with anisole in the presence of titanium(IV) chloride gave 2-(4-methoxybenzoyl)indole-3-carboxylic acid as the sole product. However, 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with anisole aff
