21859-82-5Relevant academic research and scientific papers
Oxidative organocatalytic chemoselective: N -acylation of heterocycles with aromatic and conjugated aldehydes
Ta, Linda,Sundén, Henrik
supporting information, p. 531 - 534 (2018/01/19)
Selective acylation of indoles is cumbersome often involving the need for sensitive and reactive acyl chloride derivatives or coupling reagents. Here we report a mild, functional group tolerant and highly chemoselective oxidative carbene catalyzed N-acylation of indoles with aldehydes. The acylation has a broad substrate scope and is compatible with substituents on both the aldehyde and the indole reaction partner. Furthermore, aza-heterocycles such as pyrrole and indazole can also be used as nucleophiles in this reaction providing the corresponding amide congeners in good yield.
C3-Selective alkenylation of N-acylindoles with unactivated internal alkynes by cooperative nickel/aluminium catalysis
Inoue, Fumiyoshi,Saito, Teruhiko,Semba, Kazuhiko,Nakao, Yoshiaki
supporting information, p. 4497 - 4500 (2017/04/26)
Highly regio- and stereoselective alkenylation of N-acylindoles with unactivated internal alkynes has been accomplished by cooperative nickel/aluminium catalysis to afford C3-alkenylated indoles. Coordination of the acyl moiety to a bulky aluminium-based Lewis acid plays a crucial role in the selective functionalization at the C3-position by electron-rich nickel(0) catalysis.
Site-Selective Addition of Maleimide to Indole at the C-2 Position: Ru(II)-Catalyzed C-H Activation
Lanke, Veeranjaneyulu,Bettadapur, Kiran R.,Prabhu, Kandikere Ramaiah
supporting information, p. 4662 - 4665 (2015/10/12)
Synthesis of 3-(indol-2-yl)succinimide derivatives is presented using a directing group strategy. Selective functionalization of C-2 in the presence of highly reactive C-3 in indole derivatives has been achieved. A conjugate addition product instead of He
Highly regioselective C2-alkenylation of indoles Uusing the N-benzoyl directing group: An efficient Ru-catalyzed coupling reaction
Lanke, Veeranjaneyulu,Prabhu, Kandikere Ramaiah
supporting information, p. 2818 - 2821 (2013/07/19)
A highly regioselective alkenylation of indole at the C2-position has been achieved using the Ru(II) catalyst by employing a directing group strategy. This strategy offers rare selectivity for the alkenylation N-benzoylindole at the C-2 position in the pr
Efficient N-aroylation of substituted indoles with N-aroylbenzotriazoles
Katritzky, Alan R.,Khelashvili, Levan,Mohapatra, Prabhu P.,Steel, Peter J.
, p. 3673 - 3677 (2008/09/19)
Stable and easily accessible N-aroylbenzotriazoles react with indoles in the presence of a base to afford the corresponding N-aroylindoles in yields averaging 70%. This method is effective even when both coupling reagents possess electron-donating substit
N-acylation of 5-substituted indoles with carboxylic acids via DCC coupling
Bremner, John B.,Samosorn, Siritron,Ambrus, Joseph I.
, p. 2653 - 2658 (2007/10/03)
A method for the N-acylation of 5-substituted indoles with carboxylic acids using DCC and DMAP is presented. High yields were obtained when an electron-withdrawing group was present at C-5, however the method was less effective with a C-5 electron-donating group.
Concise synthesis and structure-activity relationships of combretastatin A-4 analogues, 1-aroylindoles and 3-aroylindoles, as novel classes of potent antitubulin agents
Liou, Jing-Ping,Chang, Yi-Ling,Kuo, Fu-Ming,Chang, Chun-Wei,Tseng, Huan-Yi,Wang, Chiung-Chiu,Yang, Yung-Ning,Chang, Jang-Yang,Lee, Shiow-Ju,Hsieh, Hsing-Pang
, p. 4247 - 4257 (2007/10/03)
The synthesis and study of the structure-activity relationships of two new classes of synthetic antitubulin compounds based on 1-aroylindole and 3-aroylindole skeletons are described. Lead compounds 3, 10, and 14 displayed potent cytotoxicities with ICsu
Charge transfer fluorescence of some N-benzoylindoles
Disanayaka, Bimsara W.,Weedon, Alan C.
, p. 245 - 250 (2007/10/02)
The fluorescence properties of various N-carbonyl-substituted indoles (compounds 1-7) are examined.The N-benzoyl-indole derivatives 1 and 3-5 are shown to fluoresce weakly and the effect of solvent polarity upon the energy of the emitting state and upon the quantum yield of fluorescence is described.It is concluded that the initially formed singlet excited state is non-emissive and can relax to an intramolecular charge transfer state which is weakly fluorescent.The solvent effects are consistent with a general type of solvent interaction, and the solvent-induced shifts in the wavelength of the fluorescence emission correlate well with the Lippert equation relating the stabilisation of the excited state to a function of solvent dielectric and refractive index.A poor correlation with the empirical ET 30 solvent polarity parameter is observed.
