富含融合 sp3 的咪唑的合成。

IF 2.5 4区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

ChemistryOpen Pub Date : 2024-11-13 DOI:10.1002/open.202400272

Viacheslav Lysenko, Anton Portiankin, Tetiana Shvydenko, Svitlana Shishkina, Kostiantyn Nazarenko, Aleksandr Kostyuk

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引用次数: 0

摘要

研究人员开发了一种合成方法，用于合成具有 S、SO2、NH 和 NCbz 的饱和六元环的咪唑。它是通过结合 Neber 重排和 Marckwald 反应实现的。将 Neber 重排反应应用于环酮，使我们能够以百克为单位制备出以前未知的 α-氨基酮。不稳定的甲苯酮肟在制备后无需纯化就可立即使用。α-氨基酮与硫氰酸钾和氰酸钾发生反应，几乎可以得到高纯度的咪唑-2-硫酮或咪唑-2-酮。使用雷尼镍对咪唑-2-硫酮进行脱硫处理，可以高产率生成以前未知的 2-未取代的融合咪唑。

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Synthesis of Fused sp³-Enriched Imidazoles.

A synthetic approach to imidazoles annulated to saturated six-membered cycles featuring S, SO₂, NH, NCbz was developed. It was achieved by combining the Neber rearrangement and the Marckwald reaction. The Neber rearrangement applied to cyclic ketones allowed us to prepare in hundred gram quantities previously unknown α-amino ketones. Unstable tosyl ketoximes were used without purification immediately after their preparation. α-Amino ketones react with potassium thiocyanate and cyanate in almost a quantitative yield affording highly pure imidazol-2-thiones or imidazol-2-ones. Desulfurization of imidazole-2-thiones using Raney nickel led to the formation of previously unknown 2-unsubstituted fused imidazoles in high yields.

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来源期刊

ChemistryOpen CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

4.80

自引率

4.30%

发文量

143

审稿时长

1 months

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