NbCl5-Mg Reagent System in Regio- and Stereoselective Synthesis of (2Z)-Alkenylamines and (3Z)-Alkenylols from Substituted 2-Alkynylamines and 3-Alkynylols
The reduction of N,N-disubstituted 2-alkynylamines and substituted 3-alkynylols using the NbCl5-Mg reagent system affords the corresponding dideuterated (2Z)-alkenylamine and (3Z)-alkenylol derivatives in high yields in a regio- and stereoselective manner through the deuterolysis (or hydrolysis). The reaction of substituted propargylamines and homopropargylic alcohols with the in situ generated low-valent niobium complex (based on the reaction of NbCl5 with magnesium metal) is an efficient tool for the synthesis of allylamines and homoallylic alcohols bearing a 1,2-disubstituted double bond. It was found that the well-known approach for the reduction of alkynes based on the use of the TaCl5-Mg reagent system does not work for 2-alkynylamines and 3-alkynylols. Thus, this article reveals a difference in the behavior of two reagent systems-NbCl5-Mg and TaCl5-Mg, in relation to oxygen- and nitrogen-containing alkynes. A regio- and stereoselective method was developed for the synthesis of nitrogen-containing E-β-chlorovinyl sulfides based on the reaction of 2-alkynylamines with three equivalents of methanesulfonyl chloride in the presence of stoichiometric amounts of niobium(V) chloride and magnesium metal in toluene.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:26 |
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| Enthalten in: |
Molecules (Basel, Switzerland) - 26(2021), 12 vom: 18. Juni |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Kadikova, Rita N [VerfasserIn] |
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| Links: |
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| Themen: |
2-alkenylamines |
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| Anmerkungen: |
Date Revised 02.04.2024 published: Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.3390/molecules26123722 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM327539038 |
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| 100 | 1 | |a Kadikova, Rita N |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a NbCl5-Mg Reagent System in Regio- and Stereoselective Synthesis of (2Z)-Alkenylamines and (3Z)-Alkenylols from Substituted 2-Alkynylamines and 3-Alkynylols |
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| 500 | |a Date Revised 02.04.2024 | ||
| 500 | |a published: Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a The reduction of N,N-disubstituted 2-alkynylamines and substituted 3-alkynylols using the NbCl5-Mg reagent system affords the corresponding dideuterated (2Z)-alkenylamine and (3Z)-alkenylol derivatives in high yields in a regio- and stereoselective manner through the deuterolysis (or hydrolysis). The reaction of substituted propargylamines and homopropargylic alcohols with the in situ generated low-valent niobium complex (based on the reaction of NbCl5 with magnesium metal) is an efficient tool for the synthesis of allylamines and homoallylic alcohols bearing a 1,2-disubstituted double bond. It was found that the well-known approach for the reduction of alkynes based on the use of the TaCl5-Mg reagent system does not work for 2-alkynylamines and 3-alkynylols. Thus, this article reveals a difference in the behavior of two reagent systems-NbCl5-Mg and TaCl5-Mg, in relation to oxygen- and nitrogen-containing alkynes. A regio- and stereoselective method was developed for the synthesis of nitrogen-containing E-β-chlorovinyl sulfides based on the reaction of 2-alkynylamines with three equivalents of methanesulfonyl chloride in the presence of stoichiometric amounts of niobium(V) chloride and magnesium metal in toluene | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a 2-alkenylamines | |
| 650 | 4 | |a chlorothiolation | |
| 650 | 4 | |a homopropargylic alcohols | |
| 650 | 4 | |a magnesium metal | |
| 650 | 4 | |a methanesulfonyl chloride | |
| 650 | 4 | |a niobium(V) chloride | |
| 650 | 4 | |a substituted 2-alkynylamines | |
| 700 | 1 | |a Gabdullin, Azat M |e verfasserin |4 aut | |
| 700 | 1 | |a Mozgovoj, Oleg S |e verfasserin |4 aut | |
| 700 | 1 | |a Ramazanov, Ilfir R |e verfasserin |4 aut | |
| 700 | 1 | |a Dzhemilev, Usein M |e verfasserin |4 aut | |
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| 773 | 1 | 8 | |g volume:26 |g year:2021 |g number:12 |g day:18 |g month:06 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.3390/molecules26123722 |3 Volltext |
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