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

被引:28
|
作者
Morgans, Garreth L. [1 ]
Ngidi, E. Lindani [1 ]
Madeley, Lee G. [1 ]
Khanye, Setshaba D. [1 ]
Michael, Joseph P. [1 ]
de Koning, Charles B. [1 ]
van Otterlo, Willem A. L. [1 ]
机构
[1] Univ Witwatersrand, Sch Chem, Inst Mol Sci, ZA-2050 Johannesburg, South Africa
基金
新加坡国家研究基金会;
关键词
Ring-closing metathesis; Isomerization; 1,4-Benzodioxins; 4H-1,4-Benzoxazines; Benzodithiin; 1,4-Benzoxathiin; DOUBLE-BOND MIGRATION; OPENING/CROSS-METATHESIS; NORBORNENE DERIVATIVES; RUTHENIUM CARBENE; RECEPTOR AGONISTS; SYSTEMS; ALLYL; COMPLEXES; CATALYSTS; 1,4-BENZODIOXINS;
D O I
10.1016/j.tet.2009.10.061
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:10650 / 10659
页数:10
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