Furan recyclization reaction as a new approach to isochromenes
Furan recyclization reaction as a new approach to isochromenes
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DOI：
10.1055/s-2008-1072580
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发表时间：
2008-06-02
影响因子：
2.6
通讯作者：
Shashkov, Alexander S.
中科院分区：
文献类型：
--
作者：
Butin, Alexander V.;Abaev, Vladimir T.;Shashkov, Alexander S.
作为我们对由邻位取代的苄基呋喃合成苯环杂环化合物的持续兴趣的一部分，我们研究了[o-(羟甲基)芳基]二呋喃甲烷的环化反应。结果表明，在酸性条件下，这些化合物中的邻羟甲基起亲核作用，并通过环合-环合串联序列形成四环异色烯衍生物。或者，可以通过用氢化铝锂还原相应的异色酮衍生物来合成这些化合物。通过异色酮衍生物与过量的甲基碘化镁相互作用，还得到了具有生物活性的大麻类类似物。
As part of our ongoing interest in the synthesis of benzannelated heterocycles from o-substituted benzylfurans, recyclization of [o-(hydroxymethyl)aryl] difuryl methanes was studied. It was shown that, under acidic conditions, the o-hydroxymethyl group in these compounds acts as a nucleophile and tetracyclic isochromene derivatives are formed via a recyclization-cyclization tandem sequence. Alternatively, these compounds can be synthesized by reduction of the corresponding isochromone derivatives with lithium aluminum hydride. The potent biologically active analogues of cannabinoids were also obtained by interaction of isochromone derivatives with excess of methylmagnesium iodide.