Catalyst-free and atom-economical 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines: Facile synthesis of isoquinoline-fused spirocycles
A highly efficient and environmentally benign 1,3-dipolar cycloaddition of C,N - cyclic azomethine imines with 5-alkenyl thiazolones and 2-arylidenindane-1,3-diones is developed for the construction of congested quaternary spiro-carbon centers. All these transformations can be smoothly performed in...
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| Format: | Article |
| Language: | English |
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KeAi Communications Co. Ltd.
2022-02-01
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| Series: | Green Synthesis and Catalysis |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666554921001071 |
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| author | Lesong Li Tao Liu Xiaoli Zhang Xiaohan Hou Hao Dong Xiaoyang Li Weiwu Ren Yang Wang |
| author_facet | Lesong Li Tao Liu Xiaoli Zhang Xiaohan Hou Hao Dong Xiaoyang Li Weiwu Ren Yang Wang |
| author_sort | Lesong Li |
| collection | DOAJ |
| description | A highly efficient and environmentally benign 1,3-dipolar cycloaddition of C,N - cyclic azomethine imines with 5-alkenyl thiazolones and 2-arylidenindane-1,3-diones is developed for the construction of congested quaternary spiro-carbon centers. All these transformations can be smoothly performed in ethanol at room temperature, providing a catalyst-free and atom-economical access to diversely substituted novel isoquinoline-fused spirocycles in almost quantitative yields with high diastereoselectivities. The promising anti-tumor activity of these structurally novel spirocyclic compounds is reported as well. |
| first_indexed | 2024-12-11T10:12:40Z |
| format | Article |
| id | doaj.art-d325902b83e747f18a0dac73ba74e440 |
| institution | Directory Open Access Journal |
| issn | 2666-5549 |
| language | English |
| last_indexed | 2024-12-11T10:12:40Z |
| publishDate | 2022-02-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Green Synthesis and Catalysis |
| spelling | doaj.art-d325902b83e747f18a0dac73ba74e4402022-12-22T01:11:42ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492022-02-01316978Catalyst-free and atom-economical 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines: Facile synthesis of isoquinoline-fused spirocyclesLesong Li0Tao Liu1Xiaoli Zhang2Xiaohan Hou3Hao Dong4Xiaoyang Li5Weiwu Ren6Yang Wang7Molecular Synthesis Center & Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, ChinaMolecular Synthesis Center & Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, ChinaMolecular Synthesis Center & Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, ChinaMolecular Synthesis Center & Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, ChinaMolecular Synthesis Center & Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, ChinaMolecular Synthesis Center & Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, ChinaMolecular Synthesis Center & Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, China; Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology (QNLM), Qingdao, 266237, ChinaMolecular Synthesis Center & Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, China; Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology (QNLM), Qingdao, 266237, China; Corresponding author. Molecular Synthesis Center & Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, China.A highly efficient and environmentally benign 1,3-dipolar cycloaddition of C,N - cyclic azomethine imines with 5-alkenyl thiazolones and 2-arylidenindane-1,3-diones is developed for the construction of congested quaternary spiro-carbon centers. All these transformations can be smoothly performed in ethanol at room temperature, providing a catalyst-free and atom-economical access to diversely substituted novel isoquinoline-fused spirocycles in almost quantitative yields with high diastereoselectivities. The promising anti-tumor activity of these structurally novel spirocyclic compounds is reported as well.http://www.sciencedirect.com/science/article/pii/S2666554921001071Catalyst-freeAtom-economical1,3-Dipolar cycloadditionC,N-cyclic azomethine imine5-Alkenyl thiazolone2-Arylidenindane-1,3-dione |
| spellingShingle | Lesong Li Tao Liu Xiaoli Zhang Xiaohan Hou Hao Dong Xiaoyang Li Weiwu Ren Yang Wang Catalyst-free and atom-economical 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines: Facile synthesis of isoquinoline-fused spirocycles Green Synthesis and Catalysis Catalyst-free Atom-economical 1,3-Dipolar cycloaddition C,N-cyclic azomethine imine 5-Alkenyl thiazolone 2-Arylidenindane-1,3-dione |
| title | Catalyst-free and atom-economical 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines: Facile synthesis of isoquinoline-fused spirocycles |
| title_full | Catalyst-free and atom-economical 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines: Facile synthesis of isoquinoline-fused spirocycles |
| title_fullStr | Catalyst-free and atom-economical 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines: Facile synthesis of isoquinoline-fused spirocycles |
| title_full_unstemmed | Catalyst-free and atom-economical 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines: Facile synthesis of isoquinoline-fused spirocycles |
| title_short | Catalyst-free and atom-economical 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines: Facile synthesis of isoquinoline-fused spirocycles |
| title_sort | catalyst free and atom economical 1 3 dipolar cycloaddition of c n cyclic azomethine imines facile synthesis of isoquinoline fused spirocycles |
| topic | Catalyst-free Atom-economical 1,3-Dipolar cycloaddition C,N-cyclic azomethine imine 5-Alkenyl thiazolone 2-Arylidenindane-1,3-dione |
| url | http://www.sciencedirect.com/science/article/pii/S2666554921001071 |
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