4.5 Article

Microwave-Assisted Domino Benzannulation of a-Oxo Ketenes: Preparation of 1,3-Dihydro-2H-1,5-benzodiazepin-2-ones

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 12, Pages 2338-2345

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200093

Keywords

Annulation; Diazo compounds; Microwave chemistry; Nitrogen heterocycles; Domino reactions

Funding

  1. Aix-Marseille Universite
  2. Centre National de la Recherche Scientifique (CNRS)
  3. Departamento Administrativo de Ciencia, Tecnologia e Innovacion (COLCIEN-CIAS)
  4. Universidad del Valle
  5. Ecole Normale Superieure (ENS) Cachan

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The microwave irradiation of a series of 2-diazo-1,3-diketones in the presence of an o-phenylenediamine derivative triggered a domino Wolff rearrangement/nucleophilic addition/intramolecular imination sequence to provide a new synthetic entry to 1,3-dihydr-2H-1,5-benzodiazepin-2-ones, a class of molecules with important biological properties.

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