Literature DB >> 26661053

Synthesis of Spirocyclic Indolenines.

Michael J James1, Peter O'Brien1, Richard J K Taylor1, William P Unsworth2.   

Abstract

This Review provides an in-depth account of the synthesis of spirocyclic indolenines. Over the last 77 years, a wide array of diverse synthetic methods has been developed in order to generate these synthetically useful and biologically important spirocyclic scaffolds. The main synthetic strategies discussed are grouped into three main categories, namely interrupted Fischer indolisations, dearomatisation reactions of indoles and condensation reactions. The historical background, common synthetic challenges, current state-of-the-art and future perspectives of this field are examined.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  3H-indoles; dearomatisation; indolenines; spirocycles; spiroindolenines

Mesh:

Substances:

Year:  2015        PMID: 26661053     DOI: 10.1002/chem.201503835

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  15 in total

1.  Synthesis of 3,3'-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates.

Authors:  Arijit A Adhikari; Léa Radal; John D Chisholm
Journal:  Synlett       Date:  2017-07-11       Impact factor: 2.454

2.  Carbodefluorination of fluoroalkyl ketones via a carbene-initiated rearrangement strategy.

Authors:  Linxuan Li; Xinyu Zhang; Yongquan Ning; Xiaolong Zhang; Binbin Liu; Zhansong Zhang; Paramasivam Sivaguru; Giuseppe Zanoni; Shuang Li; Edward A Anderson; Xihe Bi
Journal:  Nat Commun       Date:  2022-07-25       Impact factor: 17.694

3.  I(III)-Catalyzed Oxidative Cyclization-Migration Tandem Reactions of Unactivated Anilines.

Authors:  Tianning Deng; Emily Shi; Elana Thomas; Tom G Driver
Journal:  Org Lett       Date:  2020-10-30       Impact factor: 6.005

4.  Solvent-free synthesis of new spiropyrroloindole compounds using Fe3O4/TiO2/MWCNTs MNCs via multicomponent reactions: assessment of new spiropyrroloindole antioxidant activity.

Authors:  Nasrin Karami Hezarcheshmeh; Javad Azizian
Journal:  Mol Divers       Date:  2022-01-31       Impact factor: 3.364

5.  From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis.

Authors:  Sarah J Chambers; Graeme Coulthard; William P Unsworth; Peter O'Brien; Richard J K Taylor
Journal:  Chemistry       Date:  2016-03-23       Impact factor: 5.236

6.  Total Synthesis of (±)-Exotine B.

Authors:  Bichu Cheng; Giulio Volpin; Johannes Morstein; Dirk Trauner
Journal:  Org Lett       Date:  2018-07-06       Impact factor: 6.005

7.  Dialkylation of Indoles with Trichloroacetimidates to Access 3,3-Disubstituted Indolenines.

Authors:  Tamie Suzuki; Nilamber A Mate; Arijit A Adhikari; John D Chisholm
Journal:  Molecules       Date:  2019-11-15       Impact factor: 4.411

8.  Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones.

Authors:  John T R Liddon; Michael J James; Aimee K Clarke; Peter O'Brien; Richard J K Taylor; William P Unsworth
Journal:  Chemistry       Date:  2016-05-19       Impact factor: 5.236

9.  A Simple and Broadly Applicable C-N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents.

Authors:  Xiaofeng Ma; Joshua J Farndon; Tom A Young; Natalie Fey; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-11       Impact factor: 15.336

10.  In(III)-TMSBr-Catalyzed Cascade Reaction of Diarylalkynes with Acrylates for the Synthesis of Aryldihydronaphthalene Derivatives.

Authors:  Qiu-Chi Zhang; Wen-Wei Zhang; Liang Shen; Zhi-Liang Shen; Teck-Peng Loh
Journal:  Molecules       Date:  2018-04-23       Impact factor: 4.411

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