Literature DB >> 28492644

Temperature switchable Brønsted acid-promoted selective syntheses of spiro-indolenines and quinolines.

Pavel Fedoseev1, Erik Van der Eycken.   

Abstract

A high-yielding, temperature switchable divergent approach towards the synthesis of either spiro-indolenines or quinolines is described, starting from easily available indolyl ynones. The application of TFA at rt promotes the dearomatization of the indole, resulting in the formation of the spiro-indolenine, while at higher temperature, rearrangement results in the formation of the quinoline.

Entities:  

Year:  2017        PMID: 28492644     DOI: 10.1039/c7cc02580g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  3 in total

1.  A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines.

Authors:  Nantachai Inprung; Michael J James; Richard J K Taylor; William P Unsworth
Journal:  Org Lett       Date:  2021-03-01       Impact factor: 6.005

2.  Selectivity, Speciation, and Substrate Control in the Gold-Catalyzed Coupling of Indoles and Alkynes.

Authors:  Ryan G Epton; William P Unsworth; Jason M Lynam
Journal:  Organometallics       Date:  2022-02-10       Impact factor: 3.876

3.  Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade.

Authors:  James A Rossi-Ashton; Aimee K Clarke; Richard J K Taylor; William P Unsworth
Journal:  Org Lett       Date:  2020-01-15       Impact factor: 6.005

  3 in total

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