Tunable Synthesis of 3-Hydroxylisoquinolin-1,4-dione and Isoquinolin-1-one Enabled by Copper-Catalyzed Radical 6-endo Aza-cyclization of 2-Alkynylbenzamide
In this work, switchable synthesis of isoquinolin-1-one and 3-hydroxylisoquinolin-1,4-dione from 2-alkynylbenzamide is reported. The transformation works well with good yields and a broad reaction scope. The synthetic switch for providing isoquinolin-1-one and 3-hydroxylisoquinolin-1,4-dione is enabled by the use of a N2 or O2 atmosphere. Mechanism studies show that the reaction proceeds in a regioselective manner via a N-center radical 6-endo-dig aza-cyclization pathway.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2019 |
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| Erschienen: |
2019 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:84 |
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| Enthalten in: |
The Journal of organic chemistry - 84(2019), 18 vom: 20. Sept., Seite 11763-11773 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Liu, Renzhi [VerfasserIn] |
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| Links: |
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| Themen: |
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| Anmerkungen: |
Date Completed 16.04.2020 Date Revised 16.04.2020 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.joc.9b01643 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM300459173 |
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| 245 | 1 | 0 | |a Tunable Synthesis of 3-Hydroxylisoquinolin-1,4-dione and Isoquinolin-1-one Enabled by Copper-Catalyzed Radical 6-endo Aza-cyclization of 2-Alkynylbenzamide |
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| 500 | |a Date Completed 16.04.2020 | ||
| 500 | |a Date Revised 16.04.2020 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a In this work, switchable synthesis of isoquinolin-1-one and 3-hydroxylisoquinolin-1,4-dione from 2-alkynylbenzamide is reported. The transformation works well with good yields and a broad reaction scope. The synthetic switch for providing isoquinolin-1-one and 3-hydroxylisoquinolin-1,4-dione is enabled by the use of a N2 or O2 atmosphere. Mechanism studies show that the reaction proceeds in a regioselective manner via a N-center radical 6-endo-dig aza-cyclization pathway | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 700 | 1 | |a Li, Meng |e verfasserin |4 aut | |
| 700 | 1 | |a Xie, Wenlin |e verfasserin |4 aut | |
| 700 | 1 | |a Zhou, Hongwei |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Yajing |e verfasserin |4 aut | |
| 700 | 1 | |a Qiu, Guanyinsheng |e verfasserin |4 aut | |
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