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在水中利用二芳基碘鎓盐实现无金属区域选择性形成C-N键和C-O键:N-芳基喹诺酮和芳氧基喹啉的简便合成

Metal-free regioselective formation of C-N and C-O bonds with the utilization of diaryliodonium salts in water: facile synthesis of N-arylquinolones and aryloxyquinolines.

作者信息

Mehra Manish Kumar, Tantak Mukund P, Arun V, Kumar Indresh, Kumar Dalip

机构信息

Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India.

出版信息

Org Biomol Chem. 2017 Jun 14;15(23):4956-4961. doi: 10.1039/c7ob00940b.

Abstract

Regioselective construction of crucial C-N and C-O bonds leading to N-arylquinolones and aryloxyquinolines has been accomplished by employing easily accessible diaryliodonium salts and quinolones in water under metal- and ligand-free conditions. This operationally simple strategy is significant due to mild reaction conditions, high product yields, recyclability of released iodoarenes and scalability to the gram level. The practical utility of the developed protocol was proved by the arylation of medicinally important heterocycles like acridin-9(10H)-one, 3-methylquinoxalin-2(1H)-one and 1H-benzo[d]imidazol-2(3H)-one.

摘要

通过在无金属和无配体条件下于水中使用易于获得的二芳基碘鎓盐和喹诺酮,实现了关键的C-N和C-O键的区域选择性构建,从而得到N-芳基喹诺酮和芳氧基喹啉。这种操作简单的策略具有重要意义,因为其反应条件温和、产物收率高、释放的碘芳烃可回收且可扩大至克级规模。所开发方法的实用性通过对吖啶-9(10H)-酮、3-甲基喹喔啉-2(1H)-酮和1H-苯并[d]咪唑-2(3H)-酮等具有药用价值的杂环进行芳基化得到了证明。

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