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Synthesis: 中国作者论文精选 2022-04-22

Synthesis 2021; 53(11): 1989-1999
DOI: 10.1055/s-0040-1706658

paper

Haifeng YuKehua WangXue ZhangWenju Wang

Complementary and Regioselective Synthesis of Isomeric 3-[Isoxazol-3(or 5)-yl]indoles from β-Ethylthio-β-indolyl-α,β-unsaturated Ketones

通过将β-乙硫基-β-吲哚基-α,β-不饱和酮与盐酸羟胺发生区域选择性环合反应,为异构 3-[异噁唑-3(或5)-基]吲哚的合成开发了一种简单高效互补和区域选择性合成方法。试验发现,在存在过量 NaOEt 和 EtOH 回流条件下进行环合反应,可以高收率得到 3-[异噁唑-5-基]吲哚,而采用 NaOAc 在沸腾 AcOH 中环合,可以高收率得到 3-[异噁唑-3-基]吲哚。

A simple and efficient method for the complementary and regioselective synthesis of isomeric 3-(isoxazol-5-yl)indoles and 3-(isoxazol-3-yl)indoles has been developed by the regioselective cyclocondensation reaction of β-ethylthio-β-indolyl-α,β-unsaturated ketones and hydroxylamine hydrochloride. It was found that the cyclocondensation reaction in the presence of excess NaOEt in refluxing EtOH gives 3-(isoxazol-5-yl)indoles in good yields, whereas using NaOAc in boiling AcOH gives 3-(isoxazol-3-yl)indoles in good yields.

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Synthesis

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