Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi 563000, China.
Key Laboratory of Basic Pharmacology of Ministry of Education and Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi 563000, China.
J Org Chem. 2022 Mar 18;87(6):4112-4123. doi: 10.1021/acs.joc.1c02909. Epub 2022 Mar 8.
An inexpensive copper-catalyzed sequential reaction process, proceeding via a nucleophilic attack of amine to Cu-carbene generated in situ from heterocyclic -tosylhydrazone precursors followed by a 1,2-H shift/oxidative cyclization cascade of -ylides, has been described, smoothly generating the corresponding structurally various spiro-dihydropyrrolo[1,2-]quinoxaline derivatives. Furthermore, the significance of this protocol can be also highlighted by its diverse conversions of the synthetic compounds to the potentially bioactive molecules such as the 2-substituted pyrrolo[1,2-]quinoxalins.
已描述了一种廉价的铜催化的顺序反应过程，该过程通过胺对原位生成的杂环 -对甲苯磺酰腙前体的铜卡宾的亲核攻击进行，然后进行 -ylides 的 1,2-H 转移/氧化环化级联，顺利地生成了相应的结构多样的螺二氢吡咯并[1,2-]喹喔啉衍生物。此外，该方案的重要意义还可以通过将合成化合物转化为潜在的生物活性分子（例如 2-取代的吡咯并[1,2-]喹喔啉）来突出显示。
