Department of Chemistry, Oklahoma State University, Stillwater, OK 74078-3071, USA.
Molecules. 2020 Nov 6;25(21):5168. doi: 10.3390/molecules25215168.
An efficient synthetic route to highly functionalized naphthalenes and quinolines has been developed using domino reactions between Morita-Baylis-Hillman (MBH) acetates and active methylene compounds (AMCs) promoted by anhydrous KCO in dry ,-dimethylformamide (DMF) at 23 °C. The substrates incorporate allylic acetates positioned adjacent to a Michael acceptor as well as an aromatic ring activated toward a SAr ring closure. A control experiment indicated that the initial reaction was an S2'-type displacement of a side chain acetoxy by the AMC anion to afford the alkene product bearing the added nucleophile to the SAr aromatic ring acceptor. Thus, equilibration of the alkene geometry of the initial product was required prior to cyclization. Products were isolated in good to excellent yields. Numerous cases (24) are reported, and several mechanistic possibilities are discussed.
已开发出一种使用 Morita-Baylis-Hillman (MBH) 醋酸盐和活性亚甲基化合物 (AMC) 之间的多米诺反应，在 23°C 的无水 KCO 在干燥的 -二甲基甲酰胺 (DMF) 中促进高度官能化的萘和喹啉的有效合成途径。这些底物包含烯丙基醋酸盐，其位于迈克尔受体相邻位置，以及对 SAr 环闭合具有活性的芳环。对照实验表明，初始反应是侧链乙酰氧基的 S2'-型取代，由 AMC 阴离子提供，从而获得带有添加亲核试剂的烯烃产物，亲核试剂 到 SAr 芳环受体。因此，在环化之前需要初始产物的烯烃几何平衡。在良好到优秀的产率下分离出产物。报道了许多情况（24），并讨论了几种可能的机制。
