Synthesis of 3,4,5-trisubstituted indoles via iterative directed lithiation of 1-(triisopropylsilyl)gramines
Synthesis of 3,4,5-trisubstituted indoles via iterative directed lithiation of 1-(triisopropylsilyl)gramines
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DOI：
10.1016/j.tet.2005.04.064
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发表时间：
2005-07-11
期刊：
影响因子：
2.1
通讯作者：
Iwao, M
中科院分区：
文献类型：
--
作者：
Fukuda, T;Akashima, H;Iwao, M
1-（三异丙基甲硅烷基）芦竹碱1与叔丁基锂的直接锂化，随后与三甲基甲硅烷基甲基叠氮化物反应，产生4-氨基-1-（三异丙基甲硅烷基）芦竹碱7。N-叔丁氧基羰基衍生物8在C-5处用叔丁基锂选择性地锂化，并且锂化的物质与各种亲电试剂反应，得到5-官能化的化合物9和10。从而建立了一种从容易获得的芦竹碱衍生物制备3，4，5-三取代吲哚的简便方法。(c)2005爱思唯尔有限公司保留所有权利。
Directed lithiation of 1-(triisopropylsilyl)gramines 1 with tert-butyl lithium followed by reaction with trimethylsilylmethyl azide produced 4-amino-1-(triisopropylsilyl)gramines 7. The N-tert-butoxycarbonyl derivatives 8 were lithiated selectively at C-5 with tert-butyllithium and the lithiated species were reacted with a variety of electrophiles to give 5-functionalized compounds, 9 and 10. A facile method to produce 3,4,5-trisubstituted indoles from readily available gramine derivatives is thereby established. (c) 2005 Elsevier Ltd. All rights reserved.