Thiol-Triggered Tandem Dearomative Michael Addition/Intramolecular Henry Reaction of 2-Nitrobenzofurans : Access to Sulfur-Containing Polyheterocyclic Compounds
An efficient dearomative cyclization of 2-nitrobenzofurans via a thiol-triggered tandem Michael addition/intramolecular Henry reaction has been developed. A range of thiochromeno[3,2-b]benzofuran-11-ols and tetrahydrothieno[3,2-b]benzofuran-3-ols could be obtained in up to 99% yield and up to >20:1 dr. The valuable thiochromone fused benzofurans could be prepared with the reaction of 2-nitrobenzofurans and 2-mercaptobenzaldehyde via the tandem dearomative Michael addition/intramolecular Henry reaction/rearomatization/oxidative dehydrogenation process in a one-pot two-step operation. A mechanism for the reaction was tentatively proposed.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:26 |
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| Enthalten in: |
Organic letters - 26(2024), 13 vom: 05. Apr., Seite 2623-2628 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Zhuo, Jun-Rui [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Revised 05.04.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.orglett.4c00646 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM370116488 |
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| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a An efficient dearomative cyclization of 2-nitrobenzofurans via a thiol-triggered tandem Michael addition/intramolecular Henry reaction has been developed. A range of thiochromeno[3,2-b]benzofuran-11-ols and tetrahydrothieno[3,2-b]benzofuran-3-ols could be obtained in up to 99% yield and up to >20:1 dr. The valuable thiochromone fused benzofurans could be prepared with the reaction of 2-nitrobenzofurans and 2-mercaptobenzaldehyde via the tandem dearomative Michael addition/intramolecular Henry reaction/rearomatization/oxidative dehydrogenation process in a one-pot two-step operation. A mechanism for the reaction was tentatively proposed | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Zhao, Jian-Qiang |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Lei |e verfasserin |4 aut | |
| 700 | 1 | |a Wu, Yu-Lu |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Yan-Ping |e verfasserin |4 aut | |
| 700 | 1 | |a You, Yong |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Zhen-Hua |e verfasserin |4 aut | |
| 700 | 1 | |a Zhou, Ming-Qiang |e verfasserin |4 aut | |
| 700 | 1 | |a Yuan, Wei-Cheng |e verfasserin |4 aut | |
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