一种氮-氮苯并咪唑轴手性化合物及其制备方法和应用
The synthesis of nitrogen-nitrogen benzimidazole axial chiral compounds via palladium-catalyzed asymmetric CN coupling reaction overcomes the limitations of existing techniques for synthesizing N-N axial chiral compounds, achieving high yield and enantioselectivity, and exhibiting significant antitumor activity.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- QINGDAO UNIV
- Filing Date
- 2023-10-17
- Publication Date
- 2026-07-17
AI Technical Summary
In the existing technology, the synthesis of NN-axis chiral compounds mainly focuses on electron-rich systems such as pyrrole and indole, and there are no reports on the construction of NN-benzimidazole axial chirality and its biological activity.
Using 2-bromoarylamidinium compounds as starting materials, a palladium-catalyzed asymmetric CN coupling reaction was conducted to synthesize a nitrogen-nitrogen benzimidazole axial chiral compound under mild conditions using commercially available chiral bisphosphine ligands Segphos or Xyl-BINAP. The target product was then purified by silica gel column chromatography.
The efficient synthesis of nitrogen-nitrogen benzimidazole axial chiral compounds was achieved with a yield greater than 60%, an enantioselectivity greater than 85%, and excellent antitumor activity.
Smart Images
Figure CN117402148B_ABST