DABCO-Catalyzed Mono-/Diallylation of <i>N</i>-Unsubstituted Isatin <i>N</i>,<i>N</i>′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates
Allylation of <i>N</i>-unsubstituted isatin <i>N</i>,<i>N</i>′-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1–10 mol% DABCO in DCM at room temperature, rapidly gave <i>N</i>-allylated and <i>N</i>, <i...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/7/3002 |
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| author | Qiumi Wang Sicheng Li Guosheng Yang Xinyu Zou Xi Yin Juhua Feng Huabao Chen Chunping Yang Li Zhang Cuifen Lu Guizhou Yue |
| author_facet | Qiumi Wang Sicheng Li Guosheng Yang Xinyu Zou Xi Yin Juhua Feng Huabao Chen Chunping Yang Li Zhang Cuifen Lu Guizhou Yue |
| author_sort | Qiumi Wang |
| collection | DOAJ |
| description | Allylation of <i>N</i>-unsubstituted isatin <i>N</i>,<i>N</i>′-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1–10 mol% DABCO in DCM at room temperature, rapidly gave <i>N</i>-allylated and <i>N</i>, <i>β</i>-diallylated isatin <i>N</i>,<i>N</i>′-cyclic azomethine imine 1,3-dipoles in moderate to high yields. The reaction features mild reaction conditions, easily practical operation, and short reaction times in most cases. Furthermore, the alkylated products were transformed into novel bicyclic spiropyrrolidine oxoindole derivatives through the [3+2] or [3+3]-cycloaddition with maleimides or Knoevenagel adducts. |
| first_indexed | 2024-03-11T05:29:20Z |
| format | Article |
| id | doaj.art-03ae2ea68b9949bab2b7c1d36e1b76d6 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T05:29:20Z |
| publishDate | 2023-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-03ae2ea68b9949bab2b7c1d36e1b76d62023-11-17T17:12:06ZengMDPI AGMolecules1420-30492023-03-01287300210.3390/molecules28073002DABCO-Catalyzed Mono-/Diallylation of <i>N</i>-Unsubstituted Isatin <i>N</i>,<i>N</i>′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman CarbonatesQiumi Wang0Sicheng Li1Guosheng Yang2Xinyu Zou3Xi Yin4Juhua Feng5Huabao Chen6Chunping Yang7Li Zhang8Cuifen Lu9Guizhou Yue10College of Science, Sichuan Agricultural University, Ya’an 625014, ChinaThe Yingjing County Emergency Management Agency, Ya’an 625200, ChinaCollege of Science, Sichuan Agricultural University, Ya’an 625014, ChinaCollege of Science, Sichuan Agricultural University, Ya’an 625014, ChinaCollege of Science, Sichuan Agricultural University, Ya’an 625014, ChinaCollege of Science, Sichuan Agricultural University, Ya’an 625014, ChinaCollege of Agronomy, Sichuan Agricultural University, Chengdu 611130, ChinaCollege of Agronomy, Sichuan Agricultural University, Chengdu 611130, ChinaCollege of Science, Sichuan Agricultural University, Ya’an 625014, ChinaHubei Collaborative Innovation Center for Advanced Organochemical Materials, Ministry-of-Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei University, Wuhan 430062, ChinaCollege of Science, Sichuan Agricultural University, Ya’an 625014, ChinaAllylation of <i>N</i>-unsubstituted isatin <i>N</i>,<i>N</i>′-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1–10 mol% DABCO in DCM at room temperature, rapidly gave <i>N</i>-allylated and <i>N</i>, <i>β</i>-diallylated isatin <i>N</i>,<i>N</i>′-cyclic azomethine imine 1,3-dipoles in moderate to high yields. The reaction features mild reaction conditions, easily practical operation, and short reaction times in most cases. Furthermore, the alkylated products were transformed into novel bicyclic spiropyrrolidine oxoindole derivatives through the [3+2] or [3+3]-cycloaddition with maleimides or Knoevenagel adducts.https://www.mdpi.com/1420-3049/28/7/3002azomethine imineallylationdipoleMBH carbonatecycloaddition |
| spellingShingle | Qiumi Wang Sicheng Li Guosheng Yang Xinyu Zou Xi Yin Juhua Feng Huabao Chen Chunping Yang Li Zhang Cuifen Lu Guizhou Yue DABCO-Catalyzed Mono-/Diallylation of <i>N</i>-Unsubstituted Isatin <i>N</i>,<i>N</i>′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates Molecules azomethine imine allylation dipole MBH carbonate cycloaddition |
| title | DABCO-Catalyzed Mono-/Diallylation of <i>N</i>-Unsubstituted Isatin <i>N</i>,<i>N</i>′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates |
| title_full | DABCO-Catalyzed Mono-/Diallylation of <i>N</i>-Unsubstituted Isatin <i>N</i>,<i>N</i>′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates |
| title_fullStr | DABCO-Catalyzed Mono-/Diallylation of <i>N</i>-Unsubstituted Isatin <i>N</i>,<i>N</i>′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates |
| title_full_unstemmed | DABCO-Catalyzed Mono-/Diallylation of <i>N</i>-Unsubstituted Isatin <i>N</i>,<i>N</i>′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates |
| title_short | DABCO-Catalyzed Mono-/Diallylation of <i>N</i>-Unsubstituted Isatin <i>N</i>,<i>N</i>′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates |
| title_sort | dabco catalyzed mono diallylation of i n i unsubstituted isatin i n i i n i cyclic azomethine imine 1 3 dipoles with morita baylis hillman carbonates |
| topic | azomethine imine allylation dipole MBH carbonate cycloaddition |
| url | https://www.mdpi.com/1420-3049/28/7/3002 |
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