Department of Organic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, 771 46 Olomouc, Czech Republic.
J Org Chem. 2023 Mar 3;88(5):3228-3237. doi: 10.1021/acs.joc.2c03025. Epub 2023 Feb 16.
Immobilized l-glutamic acid β-methyl ester was sulfonylated with 4-nitrobenzenesulfonyl chloride and alkylated with various α-haloketones. The resulting sulfonamides were reacted with potassium trimethylsilanolate. Then, upon cleavage from the polymer support, tetrasubstituted pyridines were produced as the result of one-step C-arylation, aldol condensation, and oxidation. When cleavage from the resin occurred before the trimethylsilanolate treatment, C-arylation was followed by enamination, which yielded trisubstituted pyrazines. Through the developed protocols, targeted synthesis of novel heterocyclic derivatives was performed using mild reaction conditions and a number of readily available starting materials.
固定化 l-谷氨酸 β-甲酯与 4-硝基苯磺酰氯进行磺化反应，并与各种α-卤代酮进行烷基化反应。得到的磺酰胺与三甲硅醇钾反应。然后，从聚合物载体上裂解后，通过一步 C-芳基化、醛醇缩合和氧化反应生成四取代吡啶。当在三甲基硅醇盐处理之前从树脂上裂解时，C-芳基化后进行烯胺化，生成三取代吡嗪。通过开发的方案，使用温和的反应条件和多种易得的起始原料，对新型杂环衍生物进行了目标合成。
