52498-87-0Relevant academic research and scientific papers
N-Acylcarbazoles and N-Acylindoles: Electronically Activated Amides for N-C(O) Cross-Coupling by Nlpto Ar Conjugation Switch
Buchspies, Jonathan,Rahman, Md. Mahbubur,Szostak, Roman,Szostak, Michal
supporting information, p. 4703 - 4709 (2020/06/17)
The development of new amide precursors for selective, catalytic activation of carbon-nitrogen bonds in amides is a fundamental objective of this emerging reactivity manifold. We report the palladium-catalyzed Suzuki-Miyaura cross-coupling of N-acylcarbazoles and N-acylindoles with arylboronic acids by a highly selective N-C(O) cleavage. The key amide bond ground-state destabilization stems from Nlp to Ar conjugation and enables us for the first time to achieve reactivity similar to that for N-acylsulfonamide and N-acylcarbamate activation in simple anilides.
Oxidative organocatalytic chemoselective: N -acylation of heterocycles with aromatic and conjugated aldehydes
Ta, Linda,Sundén, Henrik
, 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.
Facile approaches toward the synthesis of 6H-isoindolo[2,1-α]indol-6-ones via palladium-catalyzed carbonylation with carbon monoxide
Han, Qingshuai,Fu, Shurong,Zhang, Xiaofeng,Lin, Shen,Huang, Qiufeng
supporting information, p. 4165 - 4169 (2016/08/24)
Two facile methods for the preparation of 6H-isoindolo[2,1-α]indol-6-ones were developed. In the first protocol, 6H-isoindolo[2,1-α]indol-6-ones were prepared from 2-(2-iodophenyl)-1H-indoles via palladium-catalyzed intramolecular aminocarbonylation. The
Palladium-Catalyzed Carbonylative Synthesis of N -Benzoylindoles with Mo(CO)6 as the Carbon Monoxide Source
Wu, Xiao-Feng,Oschatz, Stefan,Sharif, Muhammad,Langer, Peter
, p. 2641 - 2646 (2015/09/01)
A mild and carbon monoxide gas-free palladium-catalyzed aminocarbonylation of indole has been developed for the synthesis of N-benzoylindoles. This method uses Mo(CO)6 as a convenient CO-precursor and BuPAd2 as the ligand. A number o
A novel one-pot synthesis of N-acylindoles from primary aromatic amides
Abid, Mohammed,De Paolis, Omar,T?r?k, Béla
, p. 410 - 412 (2008/09/17)
A novel one-pot synthesis of N-acylindoles via tandem cycloalkylation- annelation is described. This approach is based on the use of a strong solid-acid catalyst, montmorillonite K-10, and microwave irradiation under solvent-free conditions. The tandem cy
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.
A new approach to pyrrolophenanthridone alkaloids via intramolecular radical cyclization
Tsuge, Otohiko,Hatta, Taizo,Tsuchiyama, Hiroshi
, p. 155 - 156 (2007/10/03)
A new approach to the synthesis of pyrrolophenanthridone class of alkaloids is described. The method is based on intramolecular radical cyclization of easily accessible 1-aroyl-7-bromoindoles with Bu3SnH and AIBN.
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.
