Thiol-promoted intermolecular cyclization to synthesize 1,2,4-oxadiazoles including tioxazafen under transition metal-free conditions
A simple and efficient one-pot intermolecular annulation reaction for the synthesis of 1,2,4-oxadiazoles from amidoximes and benzyl thiols has been developed, in which benzyl thiols act as not only reactants but also organo-catalysts. The control experiments proved that thiol substrates could facilitate the dehydroaromatization step. High yield, functional group diversity and transition metal-free, extra oxidant-free, and mild conditions are the important practical features. Moreover, this protocol provides an effective alternative method for the synthesis of a commercially available broad-spectrum nematicide, tioxazafen.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:21 |
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| Enthalten in: |
Organic & biomolecular chemistry - 21(2023), 27 vom: 12. Juli, Seite 5616-5621 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Yan, Congcong [VerfasserIn] |
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| Links: |
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| Themen: |
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| Anmerkungen: |
Date Completed 12.07.2023 Date Revised 18.07.2023 published: Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1039/d3ob00770g |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM358782996 |
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| 245 | 1 | 0 | |a Thiol-promoted intermolecular cyclization to synthesize 1,2,4-oxadiazoles including tioxazafen under transition metal-free conditions |
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| 500 | |a published: Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a A simple and efficient one-pot intermolecular annulation reaction for the synthesis of 1,2,4-oxadiazoles from amidoximes and benzyl thiols has been developed, in which benzyl thiols act as not only reactants but also organo-catalysts. The control experiments proved that thiol substrates could facilitate the dehydroaromatization step. High yield, functional group diversity and transition metal-free, extra oxidant-free, and mild conditions are the important practical features. Moreover, this protocol provides an effective alternative method for the synthesis of a commercially available broad-spectrum nematicide, tioxazafen | ||
| 650 | 4 | |a Journal Article | |
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| 700 | 1 | |a Li, Jiaxin |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Jinli |e verfasserin |4 aut | |
| 700 | 1 | |a Wu, Yangjie |e verfasserin |4 aut | |
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