DMAP‐Catalyzed [4 + 3] Spiroannulation of Ninhydrin‐Derived MBH Carbonates with Acyclic Azadienes: Efficient Access to Multisubstituted Spiro[indanone‐azepine] Scaffolds
Abstract Indanedione‐containing spirocyclic derivatives are of significant interest in medicinal chemistry. However, spirofusion of indanediones with seven‐membered rings remains relatively unexplored. In this study, we report an efficient DMAP‐catalyzed [4 + 3] annulation of ninhydrin‐derived MBH carbonates with acyclic azadienes, providing a series of polysubstituted, pharmacologically interesting spiro[indanone‐azepine] derivatives in good to excellent yields (up to 98%) under mild conditons. The method is practical, tolerant of various functional groups, and allows for the rapid synthesis of a diverse range of products from simple, readily available starting materials. The successful scale‐up reaction and derivatization of the product further demonstrate the practicality and reliability of this method.
Authors
- Xiang‐Hong He (ORCID: https://orcid.org/0000-0002-1108-7880)
- Bo Han (ORCID: https://orcid.org/0000-0003-3200-4682)
- Heping Li (ORCID: https://orcid.org/0000-0003-1314-7944)
- Xiaoling Wu (ORCID: https://orcid.org/0009-0005-3758-7719)
- Qian Zhao
- Xin Zhang (ORCID: https://orcid.org/0000-0003-0047-3134)
Institutions
- Chengdu University of Traditional Chinese Medicine (CN)
Publication Details
- Journal
- Asian Journal of Organic Chemistry
- Published
- 2025-05-22
- DOI
- https://doi.org/10.1002/ajoc.202500226
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.79
Funders
- National Natural Science Foundation of China
- China Postdoctoral Science Foundation
- Chengdu University of Traditional Chinese Medicine
- Jiangxi University of Traditional Chinese Medicine
- Chengdu University