Synthesis of heterocyclic homotriptycenes.
Synthesis of heterocyclic homotriptycenes.
复制标题
杂环同三蝶烯的合成。
DOI：
10.1021/jo200110w
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发表时间：
2011
期刊：
影响因子：
--
通讯作者：
H. Meier
中科院分区：
文献类型：
--
作者：
Hong Zhang;D. Cao;Wenjie Liu;Huanfeng Jiang;H. Meier
以10，10-二杂芳基甲基-9，10-二氢蒽-9-醇6a-f为原料，通过分子内脱水反应合成了一系列含呋喃、噻吩和吡啶环的杂环同三蝶烯化合物7a-f。在酸的存在下，仲醇6a-f显示出不同的反应，这取决于所连接的杂环的电子密度。最初形成的碳正离子与富电子杂环发生亲电取代反应。跨环桥（1，7-消除）的形成导致高收率的高三蝶烯。当杂环具有中等电子密度时，存在两个竞争反应，分别通过1，4-消除反应和重排反应得到9-单取代蒽和9，10-二取代蒽。缺电子的杂环化合物发生反硝化反应，生成烃和酮。
A series of novel heterocyclic homotriptycenes bearing furan, thiophene, and pyridine rings, 7a-f, were synthesized by intramolecular dehydration reactions of 10,10-dihetarylmethyl-9,10-dihydroanthracen-9-ols 6a-f. In the presence of acids, the secondary alcohols 6a-f show different reactions which depend on the electron densities of the attached heterocyclic rings. The initially formed carbenium ions react in an electrophilic substitution with electron-rich heterocycles. The formation of a transannular bridge (1,7-elimination) leads to homotriptycenes in high yields. When the heterocyclic ring has a moderate electron density, two competitive reactions exist, which afford 9-monosubstituted anthracenes by 1,4-elimination or 9,10-disubstituted anthracenes by a rearrangement, respectively. Electron-deficient heterocycles undergo a disproportionation to give hydrocarbons and ketones.
影响因子：
4.9
作者：
Ghanem, Bader S.;Msayib, Kadhum J.;Walton, Allan
通讯作者：
Walton, Allan