Tetrahedron

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

…, LG Madeley, SD Khanye, JP Michael, CB de Koning…

Index: Morgans, Garreth L.; Ngidi, E. Lindani; Madeley, Lee G.; Khanye, Setshaba D.; Michael, Joseph P.; de Koning, Charles B.; van Otterlo, Willem A.L. Tetrahedron, 2009 , vol. 65, # 51 p. 10650 - 10659

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Citation Number: 21

Abstract

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.

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