62663-29-0Relevant academic research and scientific papers
An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles with benzylamines to prepare 3-aminoindole derivatives
Chen, Wei-Li,Li, Kun,Liang, Cui,Liang, Wang-Fu,Liao, Wei-Cong,Mo, Dong-Liang,Qiu, Pei-Wen,Su, Gui-Fa
, p. 9610 - 9616 (2021/12/09)
We report a green cascade approach to prepare a variety of 3-aminoindole derivatives in good to excellent yields through an iron(iii)-catalyzed dehydrogenative cross-coupling reaction of 2-arylindoles and primary benzylamines under mild reaction conditions. Mechanistic studies show that a cascade reaction involves a tert-butyl nitrite (TBN)-mediated nitrosation of 2-substituted indoles and a 1,5-hydrogen shift to afford indolenine oximes, sequential iron(iii)-catalyzed condensation and a 1,5-hydrogen shift over four steps in a one-pot reaction. The reaction shows a broad substrate scope of indoles and benzylamines and tolerates a wide range of functional groups. Moreover, the reaction is easily performed at the gram scale without producing waste after the reaction is completed. The 3-aminoindole product is purified by simple extraction, washing, and recrystallization without flash column chromatography. A double imine ligand containing the 3-aminoindole unit is facile to obtain in a 52% yield in one step. The present method highlights readily available starting materials, a simple purification procedure, and the usage of cheap, nontoxic, and environmentally benign iron(iii) catalysts. This journal is
Mild and selective base-free C-H arylation of heteroarenes: experiment and computation
Gemoets, Hannes P. L.,Kalvet, Indrek,Nyuchev, Alexander V.,Erdmann, Nico,Hessel, Volker,Schoenebeck, Franziska,No?l, Timothy
, p. 1046 - 1055 (2017/02/10)
A mild and selective C-H arylation strategy for indoles, benzofurans and benzothiophenes is described. The arylation method engages aryldiazonium salts as arylating reagents in equimolar amounts. The protocol is operationally simple, base free, moisture tolerant and air tolerant. It utilizes low palladium loadings (0.5 to 2.0 mol% Pd), short reaction times, green solvents (EtOAc/2-MeTHF or MeOH) and is carried out at room temperature, providing a broad substrate scope (47 examples) and excellent selectivity (C-2 arylation for indoles and benzofurans, C-3 arylation for benzothiophenes). Mechanistic experiments and DFT calculations support a Heck-Matsuda type coupling mechanism.
Multi-site cyclization via initial C-H activation using a rhodium(III) catalyst: Rapid assembly of frameworks containing indoles and indolines
Huang, Ji-Rong,Qin, Liu,Zhu, Yu-Qin,Song, Qiang,Dong, Lin
supporting information, p. 2844 - 2847 (2015/03/05)
Tandem multi-site cyclization triggered by Rh(III)-catalyzed C-H activation has been achieved for highly efficient synthesis of spirocycle indolin-3-one (C2-cyclization), benzo[a]carbazole (C3-cyclization) and an unusual indoxyl core (N1-cyclization). In particular, the synthesis of pseudo-indoxyl is typically completed within 10 min, and the reaction tolerates air, water and a range of solvents.
Anti-sunburn compositions containing 2-phenyl-indole derivatives
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, (2008/06/13)
Anti-sunburn compositions are provided which comprise, as active ingredient, at least one compound of the general formula: STR1 in which: R1 is selected from hydrogen, alkyl radicals containing 1 to about 12 carbon atoms and optionally branched carboxyalkyl radicals containing 1 to 4 carbon atoms; R2 is selected from hydrogen, alkoxy radicals containing 1 to 4 carbon atoms, at least one alkyl and carboxyalkyl radical containing 1 to 4 carbon atoms, and halogen atoms. R3 is selected from hydrogen, carboxyalkyl radicals containing 1 to 4 carbon atoms and --S--R8 radicals, each of R4, R5, R6 and R7 is independently selected from hydrogen, and alkyl, carboxyalkyl and alkoxy radicals containing 1 to 4 carbon atoms, provided that if R3 denotes hydrogen, at least one of the radicals R1 R2, R4, R5, R6 and R7 is not hydrogen, in an amount of at least about 0.05% by weight based on the total weight of the composition. These compounds have good solubility properties enabling a large number of different types of formulation to be prepared, these formulations being adjusted to meet the requirements of the skin to be protected.
