Literature DB >> 28605084

New Approach to 1,4-Benzoxazin-3-ones by Electrochemical C-H Amination.

Lars Julian Wesenberg1, Sebastian Herold1,2, Akihiro Shimizu3, Jun-Ichi Yoshida3, Siegfried R Waldvogel1,2.   

Abstract

1,4-Benzoxazin-3-ones are important structural motifs in natural products and bioactive compounds. Usually, the synthesis of benzoxazinones requires transition-metal catalysts and pre-functionalized substrates such as aryl halides. However, the anodic C-H amination of phenoxy acetates offers a very efficient and sustainable access to these heterocycles. The presented electrochemical protocol can be applied to a broad scope of alkylated substrates. Even tert-butyl moieties or halogen substituents are compatible with this versatile method.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amination; benzoxazinone; electrochemistry; nitrogen heterocycles; sustainable chemistry

Year:  2017        PMID: 28605084     DOI: 10.1002/chem.201701979

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


  6 in total

1.  Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance.

Authors:  Ming Yan; Yu Kawamata; Phil S Baran
Journal:  Chem Rev       Date:  2017-10-09       Impact factor: 60.622

2.  Electrochemically Enabled, Nickel-Catalyzed Amination.

Authors:  Chao Li; Yu Kawamata; Hugh Nakamura; Julien C Vantourout; Zhiqing Liu; Qinglong Hou; Denghui Bao; Jeremy T Starr; Jinshan Chen; Ming Yan; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-14       Impact factor: 15.336

Review 3.  Electrifying Organic Synthesis.

Authors:  Anton Wiebe; Tile Gieshoff; Sabine Möhle; Eduardo Rodrigo; Michael Zirbes; Siegfried R Waldvogel
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-07       Impact factor: 15.336

4.  Charged Tags for the Identification of Oxidative Drug Metabolites Based on Electrochemistry and Mass Spectrometry.

Authors:  Alexandra Gutmann; Lars Julian Wesenberg; Nadine Peez; Siegfried R Waldvogel; Thorsten Hoffmann
Journal:  ChemistryOpen       Date:  2020-05-06       Impact factor: 2.911

5.  Para-Fluorination of Anilides Using Electrochemically Generated Hypervalent Iodoarenes.

Authors:  Michael Berger; Marola S Lenhard; Siegfried R Waldvogel
Journal:  Chemistry       Date:  2022-06-07       Impact factor: 5.020

6.  Direct electrochemical generation of organic carbonates by dehydrogenative coupling.

Authors:  Tile Gieshoff; Vinh Trieu; Jan Heijl; Siegfried R Waldvogel
Journal:  Beilstein J Org Chem       Date:  2018-06-27       Impact factor: 2.883

  6 in total

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