93026-60-9Relevant academic research and scientific papers
Steric effects compete with aryne distortion to control regioselectivities of nucleophilic additions to 3-silylarynes
Bronner, Sarah M.,MacKey, Joel L.,Houk,Garg, Neil K.
, p. 13966 - 13969 (2012/10/29)
We report an experimental and computational study of 3-silylarynes. The addition of nucleophiles yield ortho-substituted products as a result of aryne distortion, but meta-substituted products form predominately when the nucleophile is large. Computations correctly predict the preferred site of attack observed in both nucleophilic addition and cycloaddition experiments. Nucleophilic additions to 3-tert-butylbenzyne, which is not significantly distorted, give meta-substituted products.
Kinesin spindle protein (KSP) inhibitors with 2,3-fused indole scaffolds
Oishi, Shinya,Watanabe, Toshiaki,Sawada, Jun-Ichi,Asai, Akira,Ohno, Hiroaki,Fujii, Nobutaka
experimental part, p. 5054 - 5058 (2010/09/05)
Mitotic kinesin spindle protein (KSP) is involved in the assembly of the bipolar spindle during cell division. On the basis of a common 2,3-fused indole substructure within the complex frameworks of terpendole E and other KSP inhibitors, the carbazoles with a bulky alkyl group were identified as a novel KSP inhibitory scaffold. Additionally, among several naturally occurring cell growth inhibitors with 2,3-fused indole structures,β-carboline alkaloids, harman and harmine, showed moderate inhibition of KSP.
Palladium-catalyzed direct synthesis of carbazoles via one-pot N-arylation and oxidative biaryl coupling: Synthesis and mechanistic study
Watanabe, Toshiaki,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
experimental part, p. 4720 - 4726 (2009/10/02)
(Chemical Equation Presented) An efficient catalytic system has been developed for the synthesis of carbazoles by one-pot N-arylation and oxidative biaryl coupling. A significant substituent effect of the diarylamine intermediate on oxidative coupling was observed. Mechanistic studies of oxidative coupling, including trapping of reaction intermediates and kinetic isotope effect experiments, are also presented.
