35283-09-1Relevant academic research and scientific papers
Concise Synthesis of Furo[2,3- b ]indolines via [3,3]-Sigmatropic Rearrangement of N -Alkenyloxyindoles
Shevlin, Michael,Strotman, Neil A.,Anderson, Laura L.
supporting information, p. 197 - 201 (2020/09/21)
A concise new synthetic route to furo[2,3- b ]indolines has been developed by taking advantage of the reactivity of N -alkenyloxyindole intermediates. These compounds spontaneously undergo [3,3]-sigmatropic rearrangement followed by cyclization to form hemiaminals as single diastereomers. Tin-promoted N -hydroxyindole formation followed by conjugate addition to activated alkynes provides simple and modular access to a diverse array of N -alkenyloxyindoles and their corresponding furo[2,3- b ]indolines. Microscale high-throughput experimentation was used to facilitate investigation of the scope and tolerance of this transformation and related studies on the nucleophilic aromatic substitution and rearrangement of N -hydroxyindoles with halogenated arenes have also been evaluated.
Efficient Synthesis of Functionalized β-Keto Esters and β-Diketones through Regioselective Hydration of Alkynyl Esters and Alkynyl Ketones by Use of a Cationic NHC–AuICatalyst
Tarigopula, Chandrahas,Thota, Ganesh Kumar,Balamurugan, Rengarajan
, p. 5855 - 5861 (2016/12/18)
Regioselective hydration of α-alkynyl esters and ketones by using a cationic NHC–AuIcatalyst results in β-keto esters and β-diketones, respectively. Controlled release of water in acetone by aldol self-condensation under the reaction conditions makes acetone as better solvent than 1,4-dioxane/water for the hydration of α-alkynyl esters having sensitive ester moieties.
(Ethoxycarbonyliodomethyl)triphenylphosphonium Iodide: A Convenient Reagent for the Direct Synthesis of β-Substituted Propiolic Acids via the Corresponding Esters
Chenault, Jaques,Dupin, Jean-Francois E.
, p. 498 - 499 (2007/10/02)
Reaction between (ethoxycarbonyliodomethyl)triphenylphosphonium iodide, potassium carbonate, and various aromatic or aliphatic aldehydes in a liquid solid two phases system gives β-substituted propiolic esters.The corresponding acids are obtained in good yield by hydrolysis.
