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利用甲醇作为主要 C1 源实现咪唑并吡啶的氧化磺甲基化反应。

Oxidative sulfonamidomethylation of imidazopyridines utilizing methanol as the main C1 source.

机构信息

College of Chemistry and Molecular Engineering, School of Life Sciences, Zhengzhou University, Zhengzhou 450001, People's Republic of China.

出版信息

Org Biomol Chem. 2019 May 15;17(19):4869-4878. doi: 10.1039/c9ob00596j.

Abstract

An efficient one pot, three component synthesis of C3 sulfonamidomethylated imidazopyridines has been disclosed under metal-free conditions, which utilized the commercially available and renewable reagent methanol as the main methylene source. A wide range of substituted imidazopyridines and sulfamides/amines were well tolerated to afford the corresponding products in up to 92% yield. In the isotopic labelling experiment, it was found that a minor part of the methylene also originated from DTBP. Moreover, the radical scavenger reactions were conducted, which suggested that a free-radical mechanism was probably not involved. The current methodology featured several advantages, including broad substrate scope, good functional group tolerance and high reaction efficiency.

摘要

一种高效、一锅煮、三组分的 C3 磺酰甲基化咪唑并吡啶的合成方法在无金属条件下被揭示,该方法利用市售和可再生试剂甲醇作为主要亚甲基源。各种取代的咪唑并吡啶和磺胺/胺都能很好地耐受,以高达 92%的收率得到相应的产物。在同位素标记实验中,发现 DTBP 也为亚甲基的形成提供了少量的甲基。此外,还进行了自由基清除反应,这表明该反应可能不涉及自由基机制。该方法具有许多优点,包括广泛的底物范围、良好的官能团耐受性和高反应效率。

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