A new and efficient one-pot synthesis of 2-hydroxy-1,4-dihydrobenzoxazines via a three-component Petasis reaction

Louisa Chouguiat (1) , Raouf Boulcina (1) , Bertrand Carboni (2) , Albert Demonceau (3) , Abdelmadjid Debache (1)

1 Laboratoire de Synthèse des Molécules d'intérêts Biologiques
2 ISCR - Institut des Sciences Chimiques de Rennes
3 Laboratoire de Chimie Macromoléculaire et de Catalyse Organique

The secondary amines synthesized by the reaction between 2-aminophenols and aromatic aldehydes, via the reduction of the corresponding imines, were employed in the synthesis of new 2-hydroxy-2H-1,4-benzoxazine derivatives via a one-pot Petasis multicomponent reaction in good to excellent yields.

Keywords: 2-Hydroxy-2H-1; 4-benzoxazine; Petasis reaction; Secondary amines; Multicomponent reaction

Domains: Chemical Sciences; Organic chemistry

Louisa Chouguiat, Raouf Boulcina, Bertrand Carboni, Albert Demonceau, Abdelmadjid Debache. A new and efficient one-pot synthesis of 2-hydroxy-1,4-dihydrobenzoxazines via a three-component Petasis reaction. Tetrahedron Letters, 2014, 55 (37), pp.5124-5128. ⟨10.1016/j.tetlet.2014.07.093⟩. ⟨hal-01079729⟩