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

Juan-Carlos Castillo (1) , Marc Presset (2) , Rodrigo Abonia (1) , Yoann Coquerel (2) , Jean Rodriguez (2)

1 Departamento de Química
2 STeRéO

The microwave irradiation of a series of 2-diazo-1,3-diket- ones 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.

Mots clés: Annulation; Diazo compounds; Microwave chemistry; Nitrogen heterocycles; Domino reactions

Domaines: Chimie organique

Juan-Carlos Castillo, Marc Presset, Rodrigo Abonia, Yoann Coquerel, Jean Rodriguez. Microwave-Assisted Domino Benzannulation of α-Oxo Ketenes: Preparation of 1,3-Dihydro-2H-1,5-benzodiazepin-2-ones. European Journal of Organic Chemistry, 2012, pp.2338-2345. ⟨10.1002/ejoc.201200093⟩. ⟨hal-00703287⟩