76609-16-0Relevant academic research and scientific papers
Regioselective Synthesis of 2-Arylindoles via Palladium-Catalyzed Cyclization of Phenylglyoxal and 2-Anilinoacetophenones with Anilines
Benitez-Medina, G. Eliad,Ortiz-Soto, Sofía,Cabrera, Armando,Amézquita-Valencia, Manuel
, p. 3763 - 3770 (2019/06/24)
A versatile route has been developed for the synthesis of 2-arylindoles using a Pd-catalyzed tandem process. Under reductive conditions, different 2-arylindoles were synthesized from phenylglyoxal and aniline. This synthetic methodology involves a tandem reaction of four steps with high regioselectivity. Alternatively, 2-anilinoacetophenones intermediates also can be using to give access to the corresponding 2-arylindoles.
Continuous flow synthesis of indoles by Pd-catalyzed deoxygenation of 2-nitrostilbenes with carbon monoxide
Glotz, Gabriel,Gutmann, Bernhard,Hanselmann, Paul,Kulesza, Anna,Roberge, Dominique,Kappe, C. Oliver
, p. 10469 - 10478 (2017/02/15)
The palladium-catalyzed deoxygenation of o-vinylnitrobenzenes employing carbon monoxide as a terminal reductant produces indoles in a continuous flow environment. The reaction proceeds with catalyst loadings of 1 to 2 mol% Pd(OAc)2 in the presence of suitable ligands/additives and generates carbon dioxide as the only stoichiometric side-product. The reductive cyclization proceeds in a clean fashion with high initial reaction rates in the pressurized flow reactor, ultimately leading to deposition of catalytically inactive palladium(0) inside the channels of the flow device, allowing for an efficient catalyst recovery. A variety of o-vinylnitrobenzenes (o-nitrostilbenes and -styrenes) were converted to the corresponding indoles within 15 to 30 min at a reaction temperature of 140 °C to furnish products in good to excellent yields (10-20 bar CO pressure). Mechanistic aspects and the scope of the transformation are discussed.
One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines
Brand, Jonathan P.,Chevalley, Clara,Waser, Jerome
, p. 565 - 569 (2011/06/26)
The Au(III)-catalyzed cyclization of 2-alkynylanilines was combined in a one-pot procedure with the Au(I)-catalyzed C3-selective direct alkynylation of indoles using the benziodoxolone reagent TIPS-EBX to give a mild, easy and straightforward entry to 2-substituted-3-alkynylindoles. The reaction can be applied to unprotected anilines, was tolerant to functional groups and easy to carry out (RT, and requires neither an inert atmosphere nor special solvents).
Anxiolytic-like effects of N,N-dialkyl-2-phenylindol-3-ylglyoxylamides by modulation of translocator protein promoting neurosteroid biosynthesis
Da Settimo, Federico,Simorini, Francesca,Taliani, Sabrina,La Motta, Concettina,Marini, Anna Maria,Salerno, Silvia,Bellandi, Marusca,Novellino, Ettore,Greco, Giovanni,Cosimelli, Barbara,Da Pozzo, Eleonora,Costa, Barbara,Simola, Nicola,Morelli, Micaela,Martini, Claudia
supporting information; experimental part, p. 5798 - 5806 (2009/08/07)
Novel N,N-disubstituted indol-3-ylglyoxylamides (1-56), bearing different combinations of substituents R1-R5, were synthesized and evaluated as ligands of the translocator protein (TSPO), the 18 kDa protein representing the minimal f
SYNTHESIS AND MASS SPECTRAL STUDIES OF FLUORINE CONTAINING 5a, 7b, 12a, 14b-TETRAHYDROBISINDOLO BENZO DIFURANS
Joshi, Krishna C.,Pathak, Vijay N.,Gupta, Ragini
, p. 153 - 162 (2007/10/02)
2:1 Cycloadducts (-H2) are formed when various fluorinated 2-arylindoles are stirred with p-benzoquinone in acidic medium and are identified as dimers of the type 5a, 7b, 12a, 14b-tetrahydrobisindolo benzo difurans.All the synthesized compounds have been characterized by their analytical and spectral (IR, PMR, 19F NMR and Mass) data.
Synthesis of Some New Fluorinated Indoles and Benzindoles through Pyridinium Ylids
Bansal, R. K.,Bhagchandani, Gope
, p. 801 - 802 (2007/10/02)
Three fluorinated phenacylpyridinium bromides (1a-c) have been prepared and reacted with various anilines to obtain 2-(fluoroaryl)indoles (3a-r).A similar reaction of 1 with 1- and 2-naphthylamines furnishes 2-(fluoroaryl)-1H-benzindoles (4a-c) and 2-(fluoroaryl)-3H-benzindoles (5a-c), respectively.All the products have been identified on the basis of elemental analyses, IR, PMR and 19F NMR spectra.
