Convenient synthesis of 5-substituted-6-methoxy or 6-hydroxy-2,3-dihydro-1,4-benzodioxins via lithiated intermediates

Thierry Besson (1) , Mohamed Hretani , Gérard Coudert , Gerald Guillaumet (2)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 ICOA - Institut de Chimie Organique et Analytique

The 6-methoxy and 6-tetrahydropyranyloxy-2,3-dihydro-1,4-benzodioxins can be lithiated at the 5-position to give intermediate lithio derivatives which react with various electrophiles to afford, after hydrolysis, 5-substituted-6-methoxy and 6-hydroxy-2,3-dihydro-1,4-benzodioxins.

Domains: Chemical Sciences; Organic chemistry; Chemical Sciences; Analytical chemistry; Chemical Sciences; Catalysis; Chemical Sciences; Medicinal Chemistry

Thierry Besson, Mohamed Hretani, Gérard Coudert, Gerald Guillaumet. Convenient synthesis of 5-substituted-6-methoxy or 6-hydroxy-2,3-dihydro-1,4-benzodioxins via lithiated intermediates. Tetrahedron, 1993, 49 (7), pp.1421-1430. ⟨10.1016/S0040-4020(01)90194-2⟩. ⟨hal-02889858⟩