级联碘化、色酮环化和氰化反应用于 2-氰基色酮的位点选择性合成。
Cascade Iodination, Chromone Annulation, and Cyanation for Site-Selective Synthesis of 2-Cyanochromones.
机构信息
National Engineering Research Center for Carbohydrate Synthesis, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China.
International Innovation Center for Forest Chemicals and Materials, Nanjing Forestry University, Nanjing 210037, China.
出版信息
J Org Chem. 2023 Mar 17;88(6):4017-4023. doi: 10.1021/acs.joc.3c00206. Epub 2023 Mar 2.
A facile cascade reaction for the site selective synthesis of 2-cyanochromones is described. By using simple -hydroxyphenyl enaminones and potassium ferrocyanide trihydrate (K[Fe(CN)]·3HO) as starting materials and I/AlCl as promoters, the products are furnished via tandem chromone ring formation and C-H cyanation. The formation of 3-iodochromone and a formal 1,2-hydrogen atom transfer (HAT) process account for the unconventional site selectivity. In addition, the synthesis of 2-cyanoquinolin-4-one has been realized by employing corresponding 2-aminophenyl enaminone as substrate.
描述了一种用于 2-氰基色酮的选择性合成的简便级联反应。以简单的 -羟基苯亚胺酮和三水合亚铁氰化钾（K[Fe(CN)]·3HO）为起始原料，I/AlCl 为促进剂，通过串联色酮环形成和 C-H 氰化反应得到产物。3-碘色酮的形成和一个形式的 1,2-氢原子转移（HAT）过程解释了非传统的位置选择性。此外，通过使用相应的 2-氨基苯亚胺酮作为底物，实现了 2-氰基喹啉-4-酮的合成。
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