Total synthesis of indoles from Tricholoma species via Bartoli/heteroaryl radical methodologies
Total synthesis of indoles from Tricholoma species via Bartoli/heteroaryl radical methodologies
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DOI：
10.1021/jo0057396
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发表时间：
2001-01-26
影响因子：
3.6
通讯作者：
Dobbs, A
中科院分区：
文献类型：
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作者：
Dobbs, A
Bartoli吲哚合成是邻位取代的硝基芳族化合物与3当量的乙烯基溴化镁反应得到7-取代的吲哚，1，2，该方法已迅速成为合成这种取代模式的吲哚的最短和最灵活的方法。1-5我们最近报道了这种方法的扩展，这表明它可能不仅限于7-取代吲哚的合成，但也可以通过这种方法获得其他取代模式的适度产率。6然而，毫无疑问，当硝基芳族化合物具有邻位取代基时，获得最好的产率，从而在3，3-σ迁移重排和随后的环化步骤中增强选择性。当然，当Bartoli方法可能是有利的时，这种邻位取代基在许多吲哚的合成中是不希望的。
The Bartoli indole synthesis is the treatment of an ortho-substituted nitro-aromatic compound with 3 equiv of vinylmagnesium bromide to give the 7-substituted indole, 1, 2 and this method has rapidly become the shortest and most flexible synthesis for indoles of this substitution pattern. 1-5 We have recently reported an extension to this methodology, suggesting that it may not be limited exclusively to the synthesis of 7-substituted indoles but that modest yields of other substitution patterns may also be obtained via this methodology. 6 However, there is no doubt that the best yields are obtained when the nitro-aromatic compound possesses an ortho substituent, enforcing selectivity in the 3, 3-sigmatropic rearrangement and subsequent cyclization step. This ortho substituent is, of course, undesirable in the synthesis of many indoles when a Bartoli approach may be advantageous.