Literature DB >> 23740873

Oxazepine synthesis by copper-catalyzed intermolecular cascade reactions between O-propargylic oximes and dipolarophiles.

Itaru Nakamura1, Yu Kudo, Masahiro Terada.   

Abstract

Three-step cascade: Oxazepine derivatives were efficiently prepared from O-propargylic oximes and dipolarophiles through copper-catalyzed cascade reactions which proceed through a 2,3-rearrangement, [3+2] cycloaddition, and subsequent 1,3-oxygen rearrangement. The process involves the cleavage of C- and N-O bonds.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  copper; cycloaddition; heterocycles; rearrangement; synthetic methods

Year:  2013        PMID: 23740873     DOI: 10.1002/anie.201302751

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  3 in total

1.  Borylated oximes: versatile building blocks for organic synthesis.

Authors:  Sean K Liew; Aleksandra Holownia; Diego B Diaz; Philip A Cistrone; Philip E Dawson; Andrei K Yudin
Journal:  Chem Commun (Camb)       Date:  2017-09-29       Impact factor: 6.222

2.  Au-catalyzed skeletal rearrangement of O-propargylic oximes via N-O bond cleavage with the aid of a Brønsted base cocatalyst.

Authors:  Keigo Shiga; Ilya D Gridnev; Masahiro Terada; Itaru Nakamura
Journal:  Chem Sci       Date:  2019-04-18       Impact factor: 9.825

3.  Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines.

Authors:  Itaru Nakamura; Mao Owada; Takeru Jo; Masahiro Terada
Journal:  Beilstein J Org Chem       Date:  2018-07-31       Impact factor: 2.883

  3 in total

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