27005-52-3Relevant articles and documents
Photoredox Cyanomethylation of Indoles: Catalyst Modification and Mechanism
O'Brien, Connor J.,Droege, Daniel G.,Jiu, Alexander Y.,Gandhi, Shivaani S.,Paras, Nick A.,Olson, Steven H.,Conrad, Jay
, p. 8926 - 8935 (2018/07/05)
The direct cyanomethylation of indoles at the 2- or 3-position was achieved via photoredox catalysis. The versatile nitrile synthon is introduced as a radical generated from bromoacetonitrile, a photocatalyst, and blue LED as a light source. The mechanism of the reaction is explored by determination of the Stern-Volmer quenching constants. By combining photophysical data and mass spectrometry to follow the catalyst decomposition, the catalyst ligands were tuned to enable synthetically useful yields of radical coupling products. A range of indole substrates with alkyl, aryl, halogen, ester, and ether functional groups participate in the reaction, affording products in 16-90% yields. The reaction allows the rapid construction of synthetically useful cyanomethylindoles, products that otherwise require several synthetic steps.
New MKLP-2 inhibitors in the paprotrain series: Design, synthesis and biological evaluations
Labrière, Christophe,Talapatra, Sandeep K.,Thoret, Sylviane,Bougeret, Cécile,Kozielski, Frank,Guillou, Catherine
, p. 721 - 734 (2016/02/09)
Members of the kinesin superfamily are involved in key functions during intracellular transport and cell division. Their involvement in cell division makes certain kinesins potential targets for drug development in cancer chemotherapy. The two most advanc
Synthesis of 2-Boryl- and silylindoles by copper-catalyzed borylative and silylative cyclization of 2-alkenylaryl isocyanides
Tobisu, Mamoru,Fujihara, Hirokazu,Koh, Keika,Chatani, Naoto
supporting information; experimental part, p. 4841 - 4847 (2010/10/19)
(Figure Presented) We have developed a method for the synthesis of 2-borylindoles via the copper(I)-catalyzed borylative cyclization of 2-alkenylphenyl isocyanides using diboronate. The reaction proceeds at room temperature under neutral conditions and exhibits high tolerance to functional groups, such as Br, CO2R, COR, CONMe2, and CN. The 2-borylindoles synthesized in the present study can be elaborated into an array of indole-based derivatives, for example, through the Suzuki-Miyaura reaction. The utility of this method is demonstrated in the rapid synthesis of a kinase inhibitor, paullone. The reaction can be extended to the synthesis of 2-hydride indole and 2-silylindole by using hydroboronate (or hydrosilane) and silylboronate, respectively. Under these copper-catalyzed conditions, a quinoxaline ring system can also be constructed by using 1,2-isocyanobenzene as a substrate.