Selective C-O Bond Forming Reactions at Indole-C2-Position toward Polycyclic Indolone or Indolinone Derivatives
Zongkang Wang1, Liqiang Yin1, Mengdan Wang1
1School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai, 200241, China.
A new chemoselective synthesis method creates complex tetracyclic indole compounds. This approach utilizes cross dehydrogenative coupling or nucleophilic addition reactions for efficient molecular construction.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Tetracyclic indole scaffolds are prevalent in biologically active molecules.
- Efficient synthetic routes to complex fused heterocycles remain a key challenge in organic synthesis.
Purpose of the Study:
- To develop a novel chemoselective methodology for synthesizing tetracyclic [1,3]oxazino[3,2-a]indol-4-one and [1,3]oxazino[3,2-a]indoline-4-one derivatives.
- To explore the utility of cross dehydrogenative coupling (CDC) and nucleophilic addition (NA) reactions in constructing these fused ring systems.
Main Methods:
- Chemoselective synthesis of tetracyclic fused heterocycles.
- Cross dehydrogenative coupling (CDC) reaction using I2 and K2CO3.
- Nucleophilic addition (NA) reaction employing a TfOH system.
Main Results:
- Successfully synthesized tetracyclic [1,3]oxazino[3,2-a]indol-4-one compounds via CDC.
- Obtained tetracyclic [1,3]oxazino[3,2-a]indoline-4-ones through NA reactions.
- Demonstrated the chemoselectivity and efficiency of both synthetic pathways.
Conclusions:
- A versatile and efficient methodology for constructing complex tetracyclic indole derivatives has been established.
- The developed CDC and NA reactions offer distinct routes to valuable fused heterocyclic scaffolds.
- This work provides a foundation for accessing novel compounds with potential pharmaceutical applications.
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