1240287-49-3Relevant articles and documents
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.
