26480-45-5Relevant academic research and scientific papers
An organocatalytic asymmetric Friedel-Crafts reaction of 2-substituted indoles with aldehydes: enantioselective synthesis of α-hydroxyl ketones by low loading of chiral phosphoric acid
Deng, Xiong-fei,Wang, Ying-wei,Zhang, Shi-qi,Li, Ling,Li, Guang-xun,Zhao, Gang,Tang, Zhuo
, p. 2499 - 2502 (2020/03/06)
Hydroxyl alkylation of indoles by Friedel-Crafts reaction with a carbonyl compound is a useful strategy. However, the reaction was restricted to ketones due to the easy formation of a bisindole byproduct. Therefore, hydroxyl alkylation of an aldehyde with indole is confronted with great challenges. Here, we report an efficient strategy for asymmetric hydroxyl alkylation of 2-substituted indoles with aldehydes under 0.1 mol% chiral phosphoric acid. A series of α-hydroxyl ketones were obtained in high yields (up to 99%) and good enantioselectivities (up to 97%).
Photoredox Generated Vinyl Radicals: Synthesis of Bisindoles and β-Carbolines
Chalotra, Neha,Ahmed, Ajaz,Rizvi, Masood Ahmad,Hussain, Zakir,Ahmed, Qazi Naveed,Shah, Bhahwal Ali
, p. 14443 - 14456 (2018/12/11)
A photoredox catalyzed approach enabling use of alkynes as surrogate of 2-oxoaldehydes/1,2-diones is reported. The method overcomes the difficulty associated with application of unsubstituted aliphatic α-oxoaldehydes, which has hitherto limited their general use. Indoles, tryptamine, and tryptophan methyl ester participated in the reaction to give a variety of α-oxo based analogues. Quantum yield investigations support a radical chain mechanism.
Multifold C-C Coupling and Unorthodox Cyclization Catalysis for Selective Synthesis of Indolotriarylmethanes, Indolocarbazoles, and Their Analogues: A Control Experiment Study
Das, Tuluma,Debnath, Sudipto,Maiti, Rituparna,Maiti, Dilip K.
, p. 688 - 700 (2017/04/26)
The selective construction of medicinally and synthetically important indole-based unsymmetrical triarylmethanes using indoles and aldehydes is challenging because the significant nucleophilicity of indole leads to C-C coupling with an azafulvene intermed
Ag nanoparticles: An efficient and versatile reagent for synthesis of bis(indolyl)methanes
Sadeghi, Bahareh,Tavasoli, Fereshteh Amiri,Hassanabadi, Alireza
, p. 1396 - 1400 (2015/05/05)
Ag nanoparticles are found to be an efficient catalyst for the electrophilic substitution reaction of indole with aldehydes to afford the corresponding bis(indolyl)methanes in good yields. The remarkable features of this new procedure are high conversions
Reaction of arylglyoxals with pyrrole or indole in aqueous media: Facile synthesis of heteroaryl α-acyloins
Anary-Abbasinejad, Mohammad,Talebizadeh, Mahdiyeh
, p. 963 - 968 (2014/08/05)
Pyrrole or indole reacts with arylglyoxal monohydrates in aqueous media in the absence of any catalyst to produce pyrrol-2-yl or indol-3-yl α-acyloin derivatives in high yields as the only product. Reactions were clean and products were isolated by simple filtration. When the reactions were carried out in acetonitrile as solvent, different products were obtained.
I2-promoted direct one-pot synthesis of 2,2-bisindolyl-1- arylethanones from multiform substrates arylethenes, 2-hydroxy-aromatic ketones, and carbinols
Jia, Feng-Cheng,Zhu, Yan-Ping,Liu, Mei-Cai,Lian, Mi,Gao, Qing-He,Cai, Qun,Wu, An-Xin
supporting information, p. 7038 - 7044 (2013/07/26)
An I2-promoted domino protocol was developed to construct 2,2-bisindolyl-1-arylethanones from multiform substrates arylethenes, 2-hydroxy-aromatic ketones, and carbinols via three distinct pathways. Through a logical coupled oxidation/Friedel-Crafts alkylation domino process, a variety of 2,2-bisindolyl-1-arylethanones were synthesized in one-pot.
Metal-free sp3 C-H bond dual-(Het)arylation: I 2-promoted domino process to construct 2,2-bisindolyl-1-arylethanones
Zhu, Yan-Ping,Liu, Mei-Cai,Jia, Feng-Cheng,Yuan, Jing-Jing,Gao, Qing-He,Lian, Mi,Wu, An-Xin
supporting information; experimental part, p. 3392 - 3395 (2012/09/08)
A molecular I2-promoted sp3 C-H bond dual-(het)arylation protocol was developed for the synthesis of 2,2-bisindolyl-1-arylethanones. Through a logical design, three mechanism-different reactions (iodination, Kornblum oxidation, and F
B(HSO4)3 as an efficient catalyst for the syntheses of bis(1H-Indol-3-yl)ethanones and bis(benzotriazol-1-yl)ethanones
Mosslemin, Mohammad Hossein,Movahhed, Abolfazl Eshghi
experimental part, p. 301 - 307 (2012/06/15)
Efficient syntheses of bis (1H-indol-3-yl)ethanones and bis (benzotriazolyl)ethanones via reaction of phenylglyoxals with indole or 1,H-benzotriazole in the presence B(HSO4)3 in solvent-free thermal and in aqueous media conditions ar
