ハロゲノベンゼンおよびニトリル間のBenzyne反応によるシアノメチル誘導体の合成とそのイソキノリン合成への応用 : 複素環式化合物の合成研究第323報

概要

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Based on a previous work that the benzyne reaction of ortho-substituted halogenobenzenes with acetonitrile gave meta-substituted benzyl cyanides as an important starting material for the syntheses of isoquinolines in a comparatively good yield, the reaction of various ortho-halogenobenzenes with nitriles, except acetonitrile, was examined for the formation of the desired meta-substituted benzyl cyanides. In this case, meta-substituted amino compounds, formed by the addition of ammonia to the benzyne intermediate, was obtained as a by-product. The benzyne reaction of halogenobenzene with other nitriles, such as phenethyl cyanide, 2-phenyl-n-butyronitrile, methylene dicyanide, and isobutyronitrile, was carried out, but the expected compounds were not obtained. Reduction of 2-(3-methoxyphenyl)propionitrile and 2-(3-benzyloxyphenyl)propionitrile gave β-methyl-3-methoxyphenethylamine and β-methyl-3-hydroxyphenethylamine, respectively, which were used as the starting materials for the synthesis of isoquinoline. Several kinds of unknown isoquinoline derivatives were obtained by phenolic cyclization or by application of Bischler-Napieralski reaction through a few steps.
公益社団法人日本薬学会の論文
1969-09-25