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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis of C-N or C-C Spiroindolines via Rearrangement Coupling Reaction
Xiaoling Liu1, Panpan Qiao1, Hui Chen1
1Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, Fujian 350116, China.
A new rearrangement coupling reaction enables the synthesis of C-N and C-C spiroindolines from tetrahydro-β-carbolines. This efficient method offers operational simplicity and mild conditions for constructing complex molecules.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Tetrahydro-β-carbolines are versatile heterocyclic scaffolds.
- Spiroindoline structures are prevalent in biologically active compounds.
Purpose of the Study:
- To develop a general and efficient method for synthesizing C-N and C-C spiroindolines.
- To utilize tetrahydro-β-carbolines as starting materials in a novel rearrangement coupling reaction.
Main Methods:
- A rearrangement coupling reaction was employed.
- Intermolecular coupling of tetrahydro-β-carbolines with anilines or indoles.
Main Results:
- The reaction effectively constructed C-N and C-C spiroindolines.
- The method demonstrated operational simplicity and mild reaction conditions.
- Good to excellent yields were achieved for a wide range of substrates.
Conclusions:
- A novel synthetic route to spiroindolines has been established.
- The developed method offers a practical approach for accessing valuable spiroindoline derivatives.
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