Synthesis of alkyl-substituted N-protected indoles via acylation and reductive deoxygenation

DM Ketcha, BA Lieurance, DFJ Homan…

文献索引：Ketcha, Daniel M.; Lieurance, Brett A.; Homan, Dominic F. J.; Gribble, Gordin W. Journal of Organic Chemistry, 1989 , vol. 54, # 18 p. 4350 - 4356

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被引用次数: 74

摘要

The synthesis of 2-, 3-, and 5-alkyl-l-(phenylsulfonyl) indoles involving Friedel-Crafts acylation followed by reductive deoxygenation is described. The application of this acylation- deoxygenation sequence to 3-acyl-l-(phenylsulfony1) indoles bearing potentially reducible functionalities was explored using sodium borohydride in trifluoroacetic acid. While halogen atoms attached to the 2-position display a predictable range of lability toward this reducing ...