Citation: Zhiguo Zhang, Bingbing Shi, Xiyang Cao, Nana Ma, Hao Wu, Xingjie Zhang, Guisheng Zhang. Anion cascade reactions Ⅲ: Synthesis of 3-isoquinuclidone bridged polycyclic lactams[J]. Chinese Chemical Letters, ;2024, 35(2): 109184. doi: 10.1016/j.cclet.2023.109184 shu

Anion cascade reactions Ⅲ: Synthesis of 3-isoquinuclidone bridged polycyclic lactams

Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

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zhangzg@htu.edu.cn

mann076@htu.edu.cn

zgs@htu.edu.cn

Received Date: 18 August 2023
Revised Date: 27 September 2023
Accepted Date: 7 October 2023
Available Online: 11 October 2023

Figures(6)

Bridged polycyclic lactams are important structural units in organic functional materials, natural products, and pharmaceuticals. A flexible and efficient anion cascade reaction was developed for the preparation of bridged polycyclic lactams from readily available malonamides and 1, 4-dien-3-ones. Various highly substituted bridged polycyclic lactams were synthesized in good to excellent yields by tandem nucleophilic sequences in the presence of BuOK in commercially available EtOH solvent at 60 ℃. Notably, the simple reactions can be run on a gram scale. Mechanistically, bis-Michael addition reaction and hemiaminalization reactions are involved in the tandem transformation.
- Anion cascade reactions,
- 3-Isoquinuclidone,
- Bridged polycyclic lactams,
- Bis-Michael addition reaction,
- Hemiaminalization
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