Base-catalyzed Formation of Enamines from β,β-Dicyanostyrene Derivatives with N-Bromosaccharin
Abstract A new method for the synthesis of functional enamines from β,β-dicyanostyrene derivatives and N-bromosaccharin(NBSA) was developed. In the presence of $ Na_{2} %$ CO_{3} $, the the reaction of β,β-dicyanostyrene derivatives with NBSA can generate the corresponding enamines smoothly in a mix...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Kang, Nan [verfasserIn] Chen, Zhanguo [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2018 |
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| Schlagwörter: |
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| Übergeordnetes Werk: |
Enthalten in: Chemical Research in Chinese Universities - Jilin University and The Editorial Department of Chemical Research in Chinese Universities, 2012, 34(2018), 5 vom: 14. Sept., Seite 751-757 |
|---|---|
| Übergeordnetes Werk: |
volume:34 ; year:2018 ; number:5 ; day:14 ; month:09 ; pages:751-757 |
| Links: |
|---|
| DOI / URN: |
10.1007/s40242-018-8055-8 |
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SPR032919875 |
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| 520 | |a Abstract A new method for the synthesis of functional enamines from β,β-dicyanostyrene derivatives and N-bromosaccharin(NBSA) was developed. In the presence of $ Na_{2} %$ CO_{3} $, the the reaction of β,β-dicyanostyrene derivatives with NBSA can generate the corresponding enamines smoothly in a mixed solvent of dichloromethane and N,N-dimethylformamide(DMF)(volume ratio 1:1) at 50 °C. The reaction of 14 kinds of β,β-dicyanostyrene derivatives with NBSA was investigated. Screened olefins afforded the corresponding enamines in good to excellent yields(up to 94%), indicating that the method has a wide adaptability for the substrate. The catalyst used is inexpensive and stable for storage. The amino groups of all products in their structures are on the α-position of products, revealing the reaction has an excellent regioselectivity. The possible pathway involving aminobromination of β,β-dicyanostyrene derivative with NBSA first and then elimination of HBr process in one pot has been proposed. The structures of all products were confirmed by 1H NMR, 13C NMR and HRMS analysis. | ||
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10.1007/s40242-018-8055-8 doi (DE-627)SPR032919875 (SPR)s40242-018-8055-8-e DE-627 ger DE-627 rakwb eng Kang, Nan verfasserin aut Base-catalyzed Formation of Enamines from β,β-Dicyanostyrene Derivatives with N-Bromosaccharin 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A new method for the synthesis of functional enamines from β,β-dicyanostyrene derivatives and N-bromosaccharin(NBSA) was developed. In the presence of $ Na_{2} %$ CO_{3} $, the the reaction of β,β-dicyanostyrene derivatives with NBSA can generate the corresponding enamines smoothly in a mixed solvent of dichloromethane and N,N-dimethylformamide(DMF)(volume ratio 1:1) at 50 °C. The reaction of 14 kinds of β,β-dicyanostyrene derivatives with NBSA was investigated. Screened olefins afforded the corresponding enamines in good to excellent yields(up to 94%), indicating that the method has a wide adaptability for the substrate. The catalyst used is inexpensive and stable for storage. The amino groups of all products in their structures are on the α-position of products, revealing the reaction has an excellent regioselectivity. The possible pathway involving aminobromination of β,β-dicyanostyrene derivative with NBSA first and then elimination of HBr process in one pot has been proposed. The structures of all products were confirmed by 1H NMR, 13C NMR and HRMS analysis. , (dpeaa)DE-He213 -Dicyanostyrene derivative (dpeaa)DE-He213 Functional enamine (dpeaa)DE-He213 Sodium carbonate (dpeaa)DE-He213 -Bromosaccharin (dpeaa)DE-He213 Chen, Zhanguo verfasserin aut Enthalten in Chemical Research in Chinese Universities Jilin University and The Editorial Department of Chemical Research in Chinese Universities, 2012 34(2018), 5 vom: 14. Sept., Seite 751-757 (DE-627)SPR03290777X nnns volume:34 year:2018 number:5 day:14 month:09 pages:751-757 https://dx.doi.org/10.1007/s40242-018-8055-8 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA AR 34 2018 5 14 09 751-757 |
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10.1007/s40242-018-8055-8 doi (DE-627)SPR032919875 (SPR)s40242-018-8055-8-e DE-627 ger DE-627 rakwb eng Kang, Nan verfasserin aut Base-catalyzed Formation of Enamines from β,β-Dicyanostyrene Derivatives with N-Bromosaccharin 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A new method for the synthesis of functional enamines from β,β-dicyanostyrene derivatives and N-bromosaccharin(NBSA) was developed. In the presence of $ Na_{2} %$ CO_{3} $, the the reaction of β,β-dicyanostyrene derivatives with NBSA can generate the corresponding enamines smoothly in a mixed solvent of dichloromethane and N,N-dimethylformamide(DMF)(volume ratio 1:1) at 50 °C. The reaction of 14 kinds of β,β-dicyanostyrene derivatives with NBSA was investigated. Screened olefins afforded the corresponding enamines in good to excellent yields(up to 94%), indicating that the method has a wide adaptability for the substrate. The catalyst used is inexpensive and stable for storage. The amino groups of all products in their structures are on the α-position of products, revealing the reaction has an excellent regioselectivity. The possible pathway involving aminobromination of β,β-dicyanostyrene derivative with NBSA first and then elimination of HBr process in one pot has been proposed. The structures of all products were confirmed by 1H NMR, 13C NMR and HRMS analysis. , (dpeaa)DE-He213 -Dicyanostyrene derivative (dpeaa)DE-He213 Functional enamine (dpeaa)DE-He213 Sodium carbonate (dpeaa)DE-He213 -Bromosaccharin (dpeaa)DE-He213 Chen, Zhanguo verfasserin aut Enthalten in Chemical Research in Chinese Universities Jilin University and The Editorial Department of Chemical Research in Chinese Universities, 2012 34(2018), 5 vom: 14. Sept., Seite 751-757 (DE-627)SPR03290777X nnns volume:34 year:2018 number:5 day:14 month:09 pages:751-757 https://dx.doi.org/10.1007/s40242-018-8055-8 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA AR 34 2018 5 14 09 751-757 |
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10.1007/s40242-018-8055-8 doi (DE-627)SPR032919875 (SPR)s40242-018-8055-8-e DE-627 ger DE-627 rakwb eng Kang, Nan verfasserin aut Base-catalyzed Formation of Enamines from β,β-Dicyanostyrene Derivatives with N-Bromosaccharin 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A new method for the synthesis of functional enamines from β,β-dicyanostyrene derivatives and N-bromosaccharin(NBSA) was developed. In the presence of $ Na_{2} %$ CO_{3} $, the the reaction of β,β-dicyanostyrene derivatives with NBSA can generate the corresponding enamines smoothly in a mixed solvent of dichloromethane and N,N-dimethylformamide(DMF)(volume ratio 1:1) at 50 °C. The reaction of 14 kinds of β,β-dicyanostyrene derivatives with NBSA was investigated. Screened olefins afforded the corresponding enamines in good to excellent yields(up to 94%), indicating that the method has a wide adaptability for the substrate. The catalyst used is inexpensive and stable for storage. The amino groups of all products in their structures are on the α-position of products, revealing the reaction has an excellent regioselectivity. The possible pathway involving aminobromination of β,β-dicyanostyrene derivative with NBSA first and then elimination of HBr process in one pot has been proposed. The structures of all products were confirmed by 1H NMR, 13C NMR and HRMS analysis. , (dpeaa)DE-He213 -Dicyanostyrene derivative (dpeaa)DE-He213 Functional enamine (dpeaa)DE-He213 Sodium carbonate (dpeaa)DE-He213 -Bromosaccharin (dpeaa)DE-He213 Chen, Zhanguo verfasserin aut Enthalten in Chemical Research in Chinese Universities Jilin University and The Editorial Department of Chemical Research in Chinese Universities, 2012 34(2018), 5 vom: 14. Sept., Seite 751-757 (DE-627)SPR03290777X nnns volume:34 year:2018 number:5 day:14 month:09 pages:751-757 https://dx.doi.org/10.1007/s40242-018-8055-8 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA AR 34 2018 5 14 09 751-757 |
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10.1007/s40242-018-8055-8 doi (DE-627)SPR032919875 (SPR)s40242-018-8055-8-e DE-627 ger DE-627 rakwb eng Kang, Nan verfasserin aut Base-catalyzed Formation of Enamines from β,β-Dicyanostyrene Derivatives with N-Bromosaccharin 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A new method for the synthesis of functional enamines from β,β-dicyanostyrene derivatives and N-bromosaccharin(NBSA) was developed. In the presence of $ Na_{2} %$ CO_{3} $, the the reaction of β,β-dicyanostyrene derivatives with NBSA can generate the corresponding enamines smoothly in a mixed solvent of dichloromethane and N,N-dimethylformamide(DMF)(volume ratio 1:1) at 50 °C. The reaction of 14 kinds of β,β-dicyanostyrene derivatives with NBSA was investigated. Screened olefins afforded the corresponding enamines in good to excellent yields(up to 94%), indicating that the method has a wide adaptability for the substrate. The catalyst used is inexpensive and stable for storage. The amino groups of all products in their structures are on the α-position of products, revealing the reaction has an excellent regioselectivity. The possible pathway involving aminobromination of β,β-dicyanostyrene derivative with NBSA first and then elimination of HBr process in one pot has been proposed. The structures of all products were confirmed by 1H NMR, 13C NMR and HRMS analysis. , (dpeaa)DE-He213 -Dicyanostyrene derivative (dpeaa)DE-He213 Functional enamine (dpeaa)DE-He213 Sodium carbonate (dpeaa)DE-He213 -Bromosaccharin (dpeaa)DE-He213 Chen, Zhanguo verfasserin aut Enthalten in Chemical Research in Chinese Universities Jilin University and The Editorial Department of Chemical Research in Chinese Universities, 2012 34(2018), 5 vom: 14. Sept., Seite 751-757 (DE-627)SPR03290777X nnns volume:34 year:2018 number:5 day:14 month:09 pages:751-757 https://dx.doi.org/10.1007/s40242-018-8055-8 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA AR 34 2018 5 14 09 751-757 |
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10.1007/s40242-018-8055-8 doi (DE-627)SPR032919875 (SPR)s40242-018-8055-8-e DE-627 ger DE-627 rakwb eng Kang, Nan verfasserin aut Base-catalyzed Formation of Enamines from β,β-Dicyanostyrene Derivatives with N-Bromosaccharin 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A new method for the synthesis of functional enamines from β,β-dicyanostyrene derivatives and N-bromosaccharin(NBSA) was developed. In the presence of $ Na_{2} %$ CO_{3} $, the the reaction of β,β-dicyanostyrene derivatives with NBSA can generate the corresponding enamines smoothly in a mixed solvent of dichloromethane and N,N-dimethylformamide(DMF)(volume ratio 1:1) at 50 °C. The reaction of 14 kinds of β,β-dicyanostyrene derivatives with NBSA was investigated. Screened olefins afforded the corresponding enamines in good to excellent yields(up to 94%), indicating that the method has a wide adaptability for the substrate. The catalyst used is inexpensive and stable for storage. The amino groups of all products in their structures are on the α-position of products, revealing the reaction has an excellent regioselectivity. The possible pathway involving aminobromination of β,β-dicyanostyrene derivative with NBSA first and then elimination of HBr process in one pot has been proposed. The structures of all products were confirmed by 1H NMR, 13C NMR and HRMS analysis. , (dpeaa)DE-He213 -Dicyanostyrene derivative (dpeaa)DE-He213 Functional enamine (dpeaa)DE-He213 Sodium carbonate (dpeaa)DE-He213 -Bromosaccharin (dpeaa)DE-He213 Chen, Zhanguo verfasserin aut Enthalten in Chemical Research in Chinese Universities Jilin University and The Editorial Department of Chemical Research in Chinese Universities, 2012 34(2018), 5 vom: 14. Sept., Seite 751-757 (DE-627)SPR03290777X nnns volume:34 year:2018 number:5 day:14 month:09 pages:751-757 https://dx.doi.org/10.1007/s40242-018-8055-8 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA AR 34 2018 5 14 09 751-757 |
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Kang, Nan |
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Kang, Nan misc , misc -Dicyanostyrene derivative misc Functional enamine misc Sodium carbonate misc -Bromosaccharin Base-catalyzed Formation of Enamines from β,β-Dicyanostyrene Derivatives with N-Bromosaccharin |
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Base-catalyzed Formation of Enamines from β,β-Dicyanostyrene Derivatives with N-Bromosaccharin , (dpeaa)DE-He213 -Dicyanostyrene derivative (dpeaa)DE-He213 Functional enamine (dpeaa)DE-He213 Sodium carbonate (dpeaa)DE-He213 -Bromosaccharin (dpeaa)DE-He213 |
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base-catalyzed formation of enamines from β,β-dicyanostyrene derivatives with n-bromosaccharin |
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Base-catalyzed Formation of Enamines from β,β-Dicyanostyrene Derivatives with N-Bromosaccharin |
| abstract |
Abstract A new method for the synthesis of functional enamines from β,β-dicyanostyrene derivatives and N-bromosaccharin(NBSA) was developed. In the presence of $ Na_{2} %$ CO_{3} $, the the reaction of β,β-dicyanostyrene derivatives with NBSA can generate the corresponding enamines smoothly in a mixed solvent of dichloromethane and N,N-dimethylformamide(DMF)(volume ratio 1:1) at 50 °C. The reaction of 14 kinds of β,β-dicyanostyrene derivatives with NBSA was investigated. Screened olefins afforded the corresponding enamines in good to excellent yields(up to 94%), indicating that the method has a wide adaptability for the substrate. The catalyst used is inexpensive and stable for storage. The amino groups of all products in their structures are on the α-position of products, revealing the reaction has an excellent regioselectivity. The possible pathway involving aminobromination of β,β-dicyanostyrene derivative with NBSA first and then elimination of HBr process in one pot has been proposed. The structures of all products were confirmed by 1H NMR, 13C NMR and HRMS analysis. |
| abstractGer |
Abstract A new method for the synthesis of functional enamines from β,β-dicyanostyrene derivatives and N-bromosaccharin(NBSA) was developed. In the presence of $ Na_{2} %$ CO_{3} $, the the reaction of β,β-dicyanostyrene derivatives with NBSA can generate the corresponding enamines smoothly in a mixed solvent of dichloromethane and N,N-dimethylformamide(DMF)(volume ratio 1:1) at 50 °C. The reaction of 14 kinds of β,β-dicyanostyrene derivatives with NBSA was investigated. Screened olefins afforded the corresponding enamines in good to excellent yields(up to 94%), indicating that the method has a wide adaptability for the substrate. The catalyst used is inexpensive and stable for storage. The amino groups of all products in their structures are on the α-position of products, revealing the reaction has an excellent regioselectivity. The possible pathway involving aminobromination of β,β-dicyanostyrene derivative with NBSA first and then elimination of HBr process in one pot has been proposed. The structures of all products were confirmed by 1H NMR, 13C NMR and HRMS analysis. |
| abstract_unstemmed |
Abstract A new method for the synthesis of functional enamines from β,β-dicyanostyrene derivatives and N-bromosaccharin(NBSA) was developed. In the presence of $ Na_{2} %$ CO_{3} $, the the reaction of β,β-dicyanostyrene derivatives with NBSA can generate the corresponding enamines smoothly in a mixed solvent of dichloromethane and N,N-dimethylformamide(DMF)(volume ratio 1:1) at 50 °C. The reaction of 14 kinds of β,β-dicyanostyrene derivatives with NBSA was investigated. Screened olefins afforded the corresponding enamines in good to excellent yields(up to 94%), indicating that the method has a wide adaptability for the substrate. The catalyst used is inexpensive and stable for storage. The amino groups of all products in their structures are on the α-position of products, revealing the reaction has an excellent regioselectivity. The possible pathway involving aminobromination of β,β-dicyanostyrene derivative with NBSA first and then elimination of HBr process in one pot has been proposed. The structures of all products were confirmed by 1H NMR, 13C NMR and HRMS analysis. |
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| title_short |
Base-catalyzed Formation of Enamines from β,β-Dicyanostyrene Derivatives with N-Bromosaccharin |
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https://dx.doi.org/10.1007/s40242-018-8055-8 |
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Chen, Zhanguo |
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2024-07-03T15:27:30.679Z |
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