College of Chemistry and Molecular Engineering, School of Life Sciences, Zhengzhou University, Zhengzhou 450001, People's Republic of China.
Org Biomol Chem. 2019 May 15;17(19):4869-4878. doi: 10.1039/c9ob00596j.
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.
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。