N-Atom Deletion in Nitrogen Heterocycles.
Haitao Qin1, Wangshui Cai1, Shuang Wang1
1Institute of Chemistry and BioMedical Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.
Angewandte Chemie (International Ed. in English)
|July 6, 2021
Summary
This study introduces a novel method for removing nitrogen atoms from N-heterocycles, enabling the creation of new molecular structures. This versatile N-atom excision strategy facilitates the synthesis of complex cyclic compounds and functionalization of inert C-H bonds.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Molecular skeletal editing is crucial for novel compound synthesis.
- Nitrogen atom excision from N-heterocycles remains an underexplored area in synthetic chemistry.
Purpose of the Study:
- To develop a versatile method for N-atom excision from N-heterocycles.
- To demonstrate the application of this method in synthesizing diverse cyclic products and modifying natural products.
Main Methods:
- N-atom excision via N-sulfonylazidonation of N-heterocycles.
- Rearrangement of sulfamoyl azide intermediates to yield cyclic products.
- Application in natural product modification and synthesis of chiral O-heterocycles.
Main Results:
- A versatile method for N-atom excision from various N-heterocycles was established.
- The method successfully generated diverse cyclic products, including chiral O-heterocycles.
- Demonstrated utility in modifying natural products and achieving formal C-H functionalization.
Conclusions:
- The developed N-atom excision strategy offers a powerful tool for skeletal editing.
- This method expands synthetic possibilities for creating complex molecules and functionalizing C-H bonds.
- The N-atom can act as a traceless directing group in synthetic sequences.
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