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.

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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

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article

DMAP‐Catalyzed [4 + 3] Spiroannulation of Ninhydrin‐Derived MBH Carbonates with Acyclic Azadienes: Efficient Access to Multisubstituted Spiro[indanone‐azepine] Scaffolds

Xiang‐Hong He, Bo Han, Heping Li, Xiaoling Wu et al.
1 citations
Asian Journal of Organic Chemistry
Fluorine in Organic Chemistry
0.79
article

DMAP‐Catalyzed [4 + 3] Spiroannulation of Ninhydrin‐Derived MBH Carbonates with Acyclic Azadienes: Efficient Access to Multisubstituted Spiro[indanone‐azepine] Scaffolds

Xiang‐Hong He, Bo Han, Heping Li, Xiaoling Wu, Qian Zhao, Xin Zhang
article en
1 citations

Abstract

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.

Asian Journal of Organic ChemistryVol. 14(8)
Chengdu University of Traditional Chinese Medicine (CN)
National Natural Science Foundation of China, China Postdoctoral Science Foundation, Chengdu University of Traditional Chinese Medicine, Jiangxi University of Traditional Chinese Medicine, Chengdu University
Openalex Percentile: Top 27%
Fluorine in Organic Chemistry
0.79
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