Synthesis of unsaturated 1,4-heteroatom-containing benzo-fused heterocycles using a sequential isomerization–ring-closing metathesis strategy

• DOI: 10.1016/j.tet.2009.10.061
• Publication Date: 2009-10-22T12:36:34Z
• Authors: Garreth L. Morgans; E. Lindani Ngidi; Lee G. Madeley; Setshaba D. Khanye; Joseph P. Michael; Charles B. de Koning; Willem A.L. van O...
• Keywords: 01 natural sciences; 0104 chemical sciences

A small library of 1,4-benzodioxins and 4H-1,4-benzoxazines was synthesized from the corresponding bis-allyloxy precursors by way of an initial isomerization to the bis-vinyloxy compounds, followed by a ring-closing metathesis using the second generation Grubbs' catalyst (G2). A related strategy, starting from benzene-1,2-dithiol and 2-mercaptophenol, afforded benzodithiin and 1,4-benzoxathiin, respectively.