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Updated: Jul 12, 2025
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
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Gold Catalyzed 7-endo-dig Hydroaminations Yielding 1,4-Diazepineones
Matthew R Nelli1, Rachel L Cantrell1, Ryan E Looper1
1Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, United States.
The Journal of Organic Chemistry
|October 27, 2023
Summary
Researchers developed a gold-catalyzed hydroamination to synthesize the 1,4-diazepindiones core found in TAN-1057 natural products. This efficient method uses readily available starting materials, creating valuable heterocyclic compounds.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Natural Product Synthesis
Background:
- The TAN-1057 family of natural products possesses a unique 1,4-diazepindiones heterocyclic core.
- Accessing this core structure is crucial for understanding and potentially synthesizing novel therapeutic agents.
Purpose of the Study:
- To develop an efficient synthetic strategy for constructing the 1,4-diazepindiones core.
- To explore gold-catalyzed reactions for accessing complex heterocyclic systems.
Main Methods:
- Synthesis of precursor amino-yneamides from readily available 1,2-diamines and alkynoic acids.
- Gold-catalyzed intramolecular hydroamination of the tethered amino-yneamides.
- Characterization of the resulting diazepineone products.
Main Results:
- Successful synthesis of the 1,4-diazepindiones heterocyclic core.
- Demonstration of a gold-catalyzed hydroamination of yneamide tethered amines as an effective cyclization strategy.
- Efficient preparation of diazepineones from accessible starting materials.
Conclusions:
- The developed gold-catalyzed hydroamination provides a robust and efficient route to the 1,4-diazepindiones core.
- This methodology facilitates access to TAN-1057 analogs and related heterocyclic compounds.
- The strategy highlights the utility of gold catalysis in constructing complex nitrogen-containing heterocycles.
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