Citation: Yan Luo, Yan-Jiao Lu, Mei-Mei Pan, Yu-Feng Liang, Wei-Min Shi, Chun-Hua Chen, Cui Liang, Gui-Fa Su, Dong-Liang Mo. Rapidly diastereoselective assembly of ten-membered N-heterocycles between two 1,3-dipoles and their diversity to access fused N-heterocycles[J]. Chinese Chemical Letters, ;2025, 36(5): 110207. doi: 10.1016/j.cclet.2024.110207 shu

Rapidly diastereoselective assembly of ten-membered N-heterocycles between two 1,3-dipoles and their diversity to access fused N-heterocycles

Yan Luo ^{a, 1} ,
Yan-Jiao Lu ^{a, 1} ,
Mei-Mei Pan ^{a, 1} ,
Yu-Feng Liang ^a ,
Wei-Min Shi ^c ,
Chun-Hua Chen ^{b, *,} ,
Cui Liang ^a ,
Gui-Fa Su ^{a, *,} ,
Dong-Liang Mo ^{a, *,}

a.
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, China
b.
Key Laboratory of Chemistry and Engineering of Forest Products, State Ethnic Affairs Commision, Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, School of Chemistry and Chemical Engineering, Guangxi Minzu University, Nanning 530006, China
c.
School of Medicine, Guangxi University of Science and Technology, Liuzhou 545006, China

ChenChunHua@gxmzu.edu.cn

gfysglgx@163.com

moeastlight@mailbox.gxnu.edu.cn

Received Date: 16 April 2024
Revised Date: 26 June 2024
Accepted Date: 2 July 2024
Available Online: 2 July 2024

Figures(10)

The development of general and practical strategies toward the construction of medium-sized rings is still challenging in organic synthesis, especially for the multiple stereocenters control of substituted groups on the ring owing to the long distance between groups. Thus, stereoselective synthesis of multi-substituted ten-membered rings is attractive. Herein, a rapid assembly of various highly substituted ten-membered nitrogen heterocycles between two 1,3-dipoles through a tandem [3 + 3] cycloaddition/aza-Claisen rearrangement of N-vinyl-α,β-unsaturated nitrones and aza-oxyallyl or oxyallyl cations are disclosed. Products containing two or multiple stereocenters could be obtained in up to 96% yield with high regioselectivity and diastereoselectivity. Selective N-O bond cleavages of ten-membered nitrogen heterocycles lead to various novel 5,6,6-perifused benzofurans, bicyclo[4.4.0] or bicyclo[5.3.0] skeletons containing three or multiple continuous stereocenters in good yields and high diastereoselectivity. Biological tests show that the obtained ten-membered N-heterocycles and bicyclo[4.4.0] skeletons inhibited nitric oxide generation in LPS-stimulated RAW264.7 cells and might serve as good anti-inflammatory agents.
- 1,3-Dipole,
- Ten-membered N-heterocycles,
- Aza-Claisen rearrangement,
- [3+3] Cycloaddition,
- Nitrone,
- Anti-inflammatory
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