An unusual four-step cascade reaction for accessing furo[3,4-c]pyridine-1,4-diones via rhodium catalysis

作者：Li, Yidi; Xu, Huiying; Zhou, Zhi^*; Huang, Lin; Tang, Zhenhao; Yi, Wei^*; Wu, Xiaowei^*

来源：Organic Chemistry Frontiers, 2023, 10(18): 4658-4664.

DOI：10.1039/d3qo00909b

• C-H ACTIVATION
• PROPARGYL ALCOHOLS
• GROUP MIGRATION
• BOND
• ANNULATION
• BENZAMIDES
• ALKYNES
• AMIDE
• CYCLIZATION
• AMIDATION

The development of efficient cascade reactions is highly important and appealing because of their desirable step-economy and convenience in constructing multiple chemical bonds and complex molecules in one shot. Herein, we report a rare four-step tandem reaction between acrylamides and 4-hydroxy-2-alkynoates to prepare novel furo[3,4-c]pyridine-1,4-diones which are difficult to synthesize by traditional methods. This unique domino reaction includes C-H activation, Lossen rearrangement, annulation, and lactonization. Additionally, this protocol features good functional group tolerance, obtainment of products by simple filtration, room temperature, and air compatibility. DFT calculations were conducted to shed some light on the reaction mechanism.

• 单位
  南方医科大学; 中国科学院研究生院; 5; 广州医学院