中国化学快报(英文版)2024,Vol.35Issue(2) :426-430.DOI:10.1016/j.cclet.2023.109184

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

Zhiguo Zhang Bingbing Shi Xiyang Cao Nana Ma Hao Wu Xingjie Zhang Guisheng Zhang
中国化学快报(英文版)2024,Vol.35Issue(2) :426-430.DOI:10.1016/j.cclet.2023.109184

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

Zhiguo Zhang 1Bingbing Shi 1Xiyang Cao 1Nana Ma 1Hao Wu 1Xingjie Zhang 1Guisheng Zhang1
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作者信息

  • 1. 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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Abstract

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 sub-stituted bridged polycyclic lactams were synthesized in good to excellent yields by tandem nucleophilic sequences in the presence of tBuOK in commercially available EtOH solvent at 60 ℃.Notably,the simple reactions can be run on a gram scale.Mechanistically,bis-Michael addition reaction and hemiaminaliza-tion reactions are involved in the tandem transformation.

Key words

Anion cascade reactions/3-Isoquinuclidone/Bridged polycyclic lactams/Bis-Michael addition reaction/Hemiaminalization

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基金项目

国家自然科学基金(21772032)

国家自然科学基金(21877206)

国家自然科学基金(22101074)

高等学校学科创新引智计划(111计划)(D17007)

Excellent Youth Foundation of Henan Scientific Committee(222300420012)

中国博士后科学基金(2019M660173)

河南省自然科学基金(202300410233)

Henan Key Laboratory of Organic Functional Molecules and Drug Innovation()

出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCD
影响因子:0.771
ISSN:1001-8417
参考文献量97
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