I2/O2 促进的色酮或 3-羟基吲哚啉-2-酮衍生物与烯胺酮的多米诺反应。
I2/O2-promoted domino reactions of isatins or 3-hydroxyindolin-2-one derivatives with enaminones.
机构信息
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, ‡College of Pharmaceutical Sciences, Soochow University , Suzhou 215123, China.
出版信息
J Org Chem. 2013 Dec 20;78(24):12362-73. doi: 10.1021/jo401773j. Epub 2013 Dec 10.
I2-promoted domino reactions of isatins or 3-hydroxyindolin-2-one derivatives with enaminones under O2 conditions have been established. The reactions of isatins with enaminones afforded functionalized tetracyclic pyrrolo[2,3,4-kl]acridine derivatives in moderate to good yields through domino cyclization and C-H oxidation. The reactions of 3-hydroxyindolin-2-one derivatives with enaminones proceeded well to give functionalized pyrrolo[2,3,4-kl]acridine derivatives via tandem ring-opening/recyclization/methyl migration sequences with two C-C bonds cleaved.
已建立了在 O2 条件下，色酮或 3-羟基吲哚啉-2-酮衍生物与烯胺酮的 I2 促进的多米诺反应。色酮与烯胺酮的反应通过多步环化和 C-H 氧化，以中等至良好的收率得到官能化的四环吡咯并[2,3,4-kl]吖啶衍生物。3-羟基吲哚啉-2-酮衍生物与烯胺酮的反应进行得很好，通过串联开环/重排/甲基迁移序列得到官能化的吡咯并[2,3,4-kl]吖啶衍生物，其中两条 C-C 键断裂。
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