116757-85-8Relevant articles and documents
Effect of solvent polarity on the regioselective hydroxyalkylation of indole with trifluoroacetaldehyde hemiacetals
Peerannawar, Swarada,Sood, Abha,Brown, Alicia,Sch?fer, Christian,Alonzo, Judith,Sutton, Steven,Christianson, Matthew,Stocking, Raven,Naclerio, Nicole,T?r?k, Béla,Landge, Shainaz M.
, p. 1941 - 1956 (2019)
The effect of solvents has been found as a crucial factor in determining the regioselectivity of the hydroxyalkylation of indole with trifluoroacetaldehyde hemiacetals. The appropriate selection of the solvent ensured to achieve absolute N1 or C3 regio/chemoselectivity of the reaction depending on the polarity and dielectric constant of the medium. Reaction conditions were optimized considering the effect of solvent, including temperature, time, and molar ratio of reactants to base. In order to rationalize this effect, density functional theory has been employed in which implicit as well as explicit role of solvent was studied, which were further validated with in situ 1H NMR spectroscopy experiments. The comparison of transition states derived from the implicit calculations revealed that the lowest energy path of the reaction in dimethyl sulfoxide (DMSO) leads to product formation with N-selectivity. Further DFT calculations on explicit interactions of indole with DMSO indicated enhanced nucleophilicity on the N atom compared to that of C3 atom, which is evident from the calculated electrostatic potential (ESP) fit charges of these complexes. These findings appear to support the experimental data and explain the N-selectivity in DMSO.
Enzyme-catalyzed kinetic resolution of 2,2,2-trifluoro-1-(heteroaryl)ethanols: Experimental and docking studies
Kucher, Olexandr V.,Kolodiazhnaya, Anastasiya O.,Smolii, Oleg B.,Prisuazhnyk, Dmytro V.,Tolmacheva, Katerina A.,Zaporozhets, Olga A.,Moroz, Yurii S.,Mykhailiuk, Pavel K.,Tolmachev, Andrey A.
, p. 7692 - 7698 (2014)
A convenient approach towards enantiopure (R) and (S) isomers of 2,2,2-trifluoro-1-(heteroaryl)ethanols was developed. The enzyme-catalyzed kinetic resolution of the corresponding racemic mixtures was achieved by using a two-step protocol that involved an
A Free-Radical-Promoted Site-Specific Cross-Dehydrogenative-Coupling of N-Heterocycles with Fluorinated Alcohols
Xu, Zhengbao,Hang, Zhaojia,Chai, Li,Liu, Zhong-Quan
, p. 4662 - 4665 (2016)
A C-C formation of an electron-rich N-heterocycle with fluorinated alcohol is developed. Through this radical-triggered cross-dehydrogenative coupling strategy, a wide range of useful building blocks such as C3 hydroxyfluoroalkylated indoles and pyrroles can be site-specifically synthesized. Mechanistic studies indicate a single-electron-transfer initiated radical cycle would be involved.
TEMPO-Mediated Cross-Dehydrogenative Coupling of Indoles and Imidazo[1,2- a]pyridines with Fluorinated Alcohols
Nipate, Dhananjay S.,Jaspal, Sonam,Shinde, Vikki N.,Rangan, Krishnan,Kumar, Anil
, p. 1373 - 1377 (2021)
A simple and highly efficient metal-free method has been developed for hydroxyfluoroalkylation of indoles and imidazo[1,2-a]pyridines via TEMPO-mediated C(sp3)-H and C(sp2)-H bond cross-dehydrogenative coupling of fluorinated alcohols and indoles. The protocol showed broad substrate scope, afforded good yields of hydroxyfluoroalkylated products, and was amenable for scale-up. Mechanistic investigation indicated involvement of the radical pathway.
High-throughput screening of bioactive compounds via new catalytic reaction in the pooled mixture
Satoh, Ayano,Nishina, Yuta
, (2019/08/20)
To increase the chances of finding new candidate molecules with medicinal properties, while expending less resource and effort, the present study used pooled substrates as starting materials. A bisindole compound that showed inhibitory activity was then isolated from the mixture, and the activity was improved by optimizing the substituents on the indole skeleton.
Directed C3-alkoxymethylation of indole via three-component cascade reaction
Pi, Chao,Yin, Xiaohang,Cui, Xiuling,Ma, Yuwen,Wu, Yangjie
supporting information, p. 2081 - 2084 (2019/03/11)
An efficient and regioselective C3-alkoxymethylation of indoles has been developed with aldehydes and alcohols via three-component cascade reaction under transition-metal free conditions. This method allows for rapid access to a variety of C3-alkoxymethyl
